How To Find Your Style with Simon Goldman

Hi guys, welcome back to Guy's Set, a guy's guide to what should be talked about. Today we are joined by Simon Goldman, a 24 year old menswear and style expert and consultant. I reached out to him because like many of you, I am completely overwhelmed by the menswear space and just style in general if I'm being honest with you, and just don't really know where to start. In this episode we talk about the one thing that can instantly upgrade any outfit.

how to build a wardrobe from scratch without breaking the bank and why your pants might be ruining your entire look. Simon shares his scrappy journey of sneaking into fashion events and cold DMing 40 brands a day with practically no followers to landing deals with brands like Ralph Lauren and gaining over 500,000 followers across social media. He gives the exact five pieces or items every guy needs in their closet, reveals the best places to shop for different budgets and breaks down what to wear for dates and to work.

This conversation is packed with actionable tips and advice that will change the way you think about getting dressed and the stress you feel around it. Without further ado, please welcome Simon Goldman to Gatsby.

Josh Felgoise (01:31.598)

All right. So Simon, can you introduce yourself and tell everybody who you are and what you do? OK, well, I'm Simon. I'm originally from Chicago and I've been in New York for about six years. At the core of everything I do is I am a menswear designer and pattern maker. So I've used to, know, so sample make and pattern make and work for lot of designers around New York. And now I pivoted, you know, middle of late covid into more.

content creation social media and that journey has changed a lot. It started with actually, know, fashion school videos, you know, what to have in your portfolio, you know, answering all the questions that nobody can really find because, you know, I struggled, you know, I don't come from a creative family. So like I was struggling with, you know, figuring out that whole art school process. And then that turned into, you know, sewing and then it turned into actually runway reviews and stuff like that and collection reviews.

then more generic menswear and now we're in a great spot where it's classic tailoring and heritage brands. They're more like educational brand history lens, which I really, really love. And I also consult for heritage brands as well. anything, whether you're a small tailor or a brand with seven years of history under your belt, and you either want to move into the US markets or want to pushing social media more or just even engaging with the younger generations, I can help with all of that.

So what you said about fashion and style is exactly why I started GuySed. It's like I couldn't find answers to these questions. So I started something to provide them. And I love that you are doing that and started that. How old are you now? I'm 24. OK. So we're the same age. OK. So have you always been interested in menswear, style, fashion and all of that? In some facet, yes. I've definitely always been interested in like craftsmanship and well-made

I don't know if it was always specifically fashion, but whether it was, I mean, like a baseball glove or a bike or something, you know, always researching and finding, you know, know, purchasing well and purchasing once. You know, I come from a family where we're not a stylish family, but my dad will buy, you know, one pair of jeans, but he'll spend, you know, it'll be a very nice pair of jeans from like a good, you know, Japanese mill and then he will wear them too. You can't wear them anymore.

Josh Felgoise (03:52.466)

And stuff like that or like he'll get a custom pair of work boots made that'll literally just laugh to last a lifetime You know, you'll resole it and resole it but it's just you know buying once and buying well But no my my inspiration and my love of style has you know changed a lot whether it started with you know watching Doctor Who and wanting to dress, you know, like some of the characters or You know getting into James Bond or all those old, know spaghetti Western films very early on, you know, it's everything's

you know, changed big time. But I think I've always been conscious about my style and my dressing, especially because when I was growing up, I was a little chubby. So, you know, that definitely, you know, played into, you know, how I got dressed every single day. What is the biggest menswear mistake you see guys making? You know, I think there's definitely a lot of mistakes being made right now, but I think like a major thing that I think could help improve everyone's outfits really easily without, you know,

I never want to get on the internet and tell people like, your style's wrong. What you're wearing is bad really, but it's more so, you know, it all comes down to fit. even if you're, you know, the basic, you know, you're just a finance bro going around, I mean, a fit of a trouser can really impact and change a whole outfit. And if your pants don't fit well, the whole outfit will feel off. It'll either age you, make you look a little bit like awkward or something. So I think, you know, the balance of a trouser and a well balanced...

pant can change up a whole outfit. doesn't matter if you're wearing, you know, you know, the finance bro vest. If your pants fit well, the whole outfit would automatically look better. So I think it's mainly a fit thing. Cause I never want to tell people, you know, wear what you want to wear. You know, everyone has their own style journey, but it really all comes down to fit. So like what, how does somebody know if it fits right? How do you know if it fits well? Like what are the, the tips for that?

I just think like a lot of things, know, I definitely think, you know, stylistically and know, silhouettes have changed a lot and all of it's really cyclical. But you know, no, no one needs a, you know, whether you're wearing like Lululemon ABC trouser or, know, Brooks Brothers or going to Bonobos or whatever, you know, we don't need any suit trousers that taper almost like a jogger sweat pant at the ankle because you know, that'll just throw off. It kind of makes you look like carrot shaped and it just doesn't create like a very, you know,

Josh Felgoise (06:16.138)

well-balanced silhouette even things like pleats, know, if your pants are too tight or they're not sitting well if the pleats are pulling open that'll mess up the whole silhouette and make you look actually like It's just kind of scrunched up or not. Everything's laying, you know flat along the fly of the trouser or even you know, if they're Sitting a little bit too low or something. There's so many little things that can that could be off and I'm not saying you don't if you like like slimmer trousers, you can wear a slimmer trouser, but

Always go for something that know tapers maybe a little bit less but tapers down from the knee and leave some room in the thigh so you can move around because nobody wants pulling everywhere because that's not comfortable for anyone. Going back what you said before about like being a chubby kid and now like obviously slimming down and finding your style and how has finding style and fashion increased your confidence? I think for a lot of reasons like I think I've always been

a little bit confident with how I dress. Because even back in the day, was wearing, I wouldn't call myself stylish at all, but I was wearing, like big, I'm a big old music fan, so was wearing fake glasses to resemble some old weather that's like Roy Orbison or Buddy Holly and a Fronora. I was not stylish, but always confident to wear what I wanted to wear. But I definitely think,

In my style journey just finding things that feel very me has you know definitely Made me feel more confident because you know I am also you know you meet a lot of these Fashion influencers and fashion people that you know are all designered up all the time wearing crazy stuff I am pretty much a uniform dresser You know not like I'm not like Tom Brown wearing the same gray suit every day But there is there is a formula to usually how I get dressed unless it's like a special event. I'm always in a good pair of

really worn in jeans that I've been wearing for years, a good pair of work boots or beat up Alden Oxfords, either a t-shirt, a button down, an old tie, and then some type of jacket or blazer. I stick to what I know works for me and feels comfortable for me, and then you kind of just play around from there.

Josh Felgoise (08:32.984)

For somebody that is starting to build their wardrobe from scratch, like what you just gave about your kind of pieces that you have, that you wear all the time, kind of like a uniform or the same kind of formula, what would you tell a person who has no idea where to start? Honestly, know, I started my style journey and fashion journey, like sewing journey in general, actually I like a thrift store because, I wanted to get

There was a, actually it's like a needles, like sewn together flannel shirt where it's like multiple different flannel shirts sewn together and show my mom. And it was, I think it was like a few hundred bucks and there's just no chance that would ever fly in my family at all. And she was like, just go make it. I think, how I started my sewing journey specifically was going to thrift stores and buying old curtains, blankets, bed sheets, tracing garments that fit me well to start resewing.

But also if you're restarting your wardrobe, just think, you know, go in. I'm not a big fan of shopping online unless I really like need to or I think if you have the luxury of having some type of good stores by you, even if it's, know, whether that's a Banana Republic, a Todd Snyder or a Buck Mason, just go in and find your fit. Because also if you go in, you're like, you know, like let's say I stopped by Buck Mason. They have some incredible silhouettes, very good.

Wardrobe building pieces. I'll always recommend people go there But let's say you put on a pair of pants there and let's say that pair of pants is out of your budget But you know with the fit you like from there works for you You just can go on their website and stuff and I'll have the full sizing breakdown of you know This is how much room is in the thigh This is how much room is you know at the leg opening at the bottom and then you can just go from there and compare that to Maybe stuff in your price point and then you could go online But you know exactly that kind of what measurements and what ballpark you're looking for

to kind of get that fit in a price point that might work for you right now. Because I think fashion is, there's a big spectrum and also like a lot of these ready to wear brands, the buy-in is so ridiculously high right now. Whereas I think you have to be like a little bit scrappier. But also look for places, I always recommend shopping on sites that usually what you're looking for the people wouldn't be shopping on. I love a lot of...

Josh Felgoise (10:59.854)

classic tailoring heritage men's brands and a lot of what I like, you I can go on Depop. I can go on the real real because I know the Depop customer and the real real customer is not looking for the brands that I like wearing. So you can find really amazing deals on those platforms if you just think, know, you know, like it's it's just so much easier. You know, you can find some really fantastic deals for the brands that, you know, those platforms are not advertising to. That's super helpful. And there are so many directions I could go in from what you just said.

I want to start with what brands you recommend like Buck Mason that you said that would be good kind of starter brands for guys to go to start finding their style, start finding things they like to wear and start building from there. What else do you recommend? So I think yeah, I think Buck Mason is kind of the standard right now for doing everything really, really well. And you know, it is not it is a

For what you're getting a lot of stuff is made in the USA I've actually been to the like knitting mill that a lot of the stuff and t-shirts are made at in Pennsylvania, but I think you know For what they're offering and how long it's gonna last I think it is a phenomenal brand to look at because like, know I love brands like Todd Snyder and stuff But if you look at a buck mason's with Todd Snyder Todd Snyder is already way more stylized And way more expensive, you know, some of these some of the buy-ins, you know, you're spending over a thousand dollars for a suit you can spend

three grand on an overcoat at Todd Snyder and I absolutely love, love, love the brand, but it's definitely not the most accessible. I gotta say if you're just starting, you I like Buck Mason, but I just recommend just being a little bit more scrappy, go to flea markets, go to thrift stores, go to consignment shops. I mean, I'm at housing works in New York all the time and like just all wherever I can find stuff because for me it's really shouldn't ever be about the brand name. It should be more about, you know, what just fits you well.

And that's kind of how I get dressed. What are the five pieces that you recommend every guy have in their wardrobe to kind of have that uniform or that fit that they can always throw together or put on any day? Like I definitely think a good like lace-up pair of derbies is great. know, everyone needs a good leather shoe. You know, there's a time and a place for sneakers, but you know, a good derby can be worn with jeans. It could be worn with, you know, suit trousers. I definitely, everyone needs a pair of

Josh Felgoise (13:20.886)

Either whether, stylistically whether you want a flat front or pleated, you know, nice pair of slacks and a good pair of trousers. Everyone needs a good pair of, you know, dark wash denim and then blank tees. You need your range of, need your, I pretty much, I usually don't wear actually any graphic tees. I just have a big collection of black and white, just blank tees. And then also...

What else do really need? An unstructured jacket. If tailoring kind of scares you and you don't want to feel really kind of like bundled up, I definitely think, you know, unstructured, you know, unlined blazer is a good way to go. And I don't even know what number I'm on that over like Oxford cloth button down. I mean, there's no more versatile shirt ever made because you can dress it up, dress it down, wear it open over a t-shirt and, know, automatically, you know, spruce up any outfit.

Are there any brands for like those jackets or the shoes you recommend to the denim? anything? I love your recommendation about like going to like a consignment or go to like a flea market or something. But like for somebody that like, I don't know, is kind of similar to me that is kind of overwhelmed by the fashion space or this, the menswear space and just wants like direction of like, okay, you should check this place out or this place out for these five items.

What do you recommend? I mean, if you want almost that capsule wardrobe that is a mixture of, you know, more casual styles, but also every piece can be dressed up just like if I'm recommending one brand to that, you know, mid 20 upper 20, even 30 year old guy that wants to like needs to start looking a little bit more put together and sophisticated. It's called Natalino.

They're out of London, but you know the most incredible sweaters, incredible shirts, trousers, suits, overcoats, mean jeans, like on all their cuts are really really good. So if I was gonna say one brand that every guy should check out or if you know you're redoing your wardrobe and you have some money to spend, I mean some of the best bang for your buck is is Natalino too. Because also their photos and their direction lends some really really good style inspiration and how to

Josh Felgoise (15:38.488)

put together some looks. Great. OK, cool. And then going back to your kind of social media career, how did you get started online? And like, it sounds like you kind of build your own schedule, build your own day, right? Like you're you kind of work for yourself. So tell me more about that. Like, is what is a day in your life look like and how did you get started on social media? So I got started on social media. I was a freshman in fashion design school. Covid hit. I went back home to Chicago.

And I wanted to know, Chicago is my favorite city in the world, but if there's one thing, it's just great fine art, great music, great everything, know, design wise, but absolutely not really no fashion and no style other than we have a very like thriving, amazing street wear community in Chicago. That's kind of actually like how I got started was by going to as many kind of way there's sneaker events, pop-ups, whatever that may be.

But if you're looking for more, I mean, tailoring and more traditional menswear, there's not really a lot of that because not a lot of people care for that there. everyone, like how I described Chicago is people will spend a few hundred dollars on a good dinner, but if you tell a guy to buy a $200 pair of pants, he'll think you're crazy. So, you know, it's, so I started posting little educational videos when I was in Chicago. And then when, you know, COVID started to, you know,

When people started to understand a little bit more what COVID was, I came back to New York to finish school and that's when I put quite a bit of strategy behind everything because I really don't think everyone will tell you, no, here are the tips to grow on social media, blah, blah, blah, blah. A lot of the times, it's all strategy. mean, I don't think there's a lot of luck in social media. Sometimes you get really lucky with some videos going absolutely crazy. But with me and my journey is I never was looking for that one major video to go

and create like insanely viral overnight. That's not the content I make. I'm extremely niche. I put myself into a corner, which I'm happy with because then I get to talk about what I'm passionate about. my whole thing was how do you slowly build a, with continuous gradual growth, a really good, strong community? And that's kind of, every single step I took in my journey was to...

Josh Felgoise (17:55.47)

follow that path because there's so many people that can get a video, gets a few million views overnight, gain 100, 200,000 followers and then a month later, everything goes back down because it's actually not building a community. You have your moment and then it's passed. So then I got to New York and I was still interning all around, sneaking into events to try to network and meet people. And then it kind of took off because I was very, very much worried about...

moving into the fashion industry and especially the design industry after graduating because there's not a lot of strong menswear design out here and I never really wanted to work in a super corporate environment. So then it was like, how do I position myself to be able to work for myself? And a lot of that was just like hardcore networking, know, sending, you know, 40 cold emails a day just to set up as many coffees as I can, DMs and just being as proactive as possible.

Tell me more about that. I'm really interested in that part of the like scrappy guy like sneaking into like shows or events messaging people like walk me through you at that time. What you even did to start because I think that's exactly how you have to do it in any type of industry when you want to work for yourself. Like tell me more about all of that. I'm really intrigued by it. So I was going through like a weird phase where I was really worried that

know the fashion industry, whoever I was, you know, at these events, you I never told anyone I was still in school. So I think there was like this weird thing where nobody really knew how old I was or whatever. Like I very much, you know, at the time I didn't have a beard. I looked like I was like, you know, 15, 16. I'm, you know, without the beard, I look like I'm 16 years old. But I, you know, I was sneaking into events. My first event that I snuck into was actually an event for...

Jim Moore, was the kind of like head of GQ for a long time, he produced over 500 issues of GQ and it was his first Hungsan Heroes, it was a book launch. And at that event, I got to meet him because he was kind of an idol. Then I started just trying to find where those spaces in the fashion industry that weren't always the coolest and most flashy for my generation of fashion. Everyone wants to go to those pop-up events, DJ sets, all that, but I was looking for...

Josh Felgoise (20:13.646)

What are the rooms to be in that have the people who are making the decisions? So, know, at that point I found, you know, the 92 Y in the Upper East Side has, you know, first off, incredible talks, incredible screenings. Like, I highly recommend every single student, everyone in New York should be going to events there. Because a lot of the student tickets, and a lot of tickets in general are very cheap and you meet some incredible people. But I was going to Fern Malice, who pretty much is one of the founders of New York Fashion Week. She started when...

Fashion Week was at the Bryant Park tents and there was like a real hub for Fashion Week. That was all her. She did these, she still does these talks called her like fashion icon talks where it'll be her on stage interviewing, whether that's a Ralph Lauren, Tommy Hilfiger, Carolina Herrera, all these massive people. And at the time I was just going buying the 20, $30 ticket and sitting there, getting there early, staying there after talking to as many people as I could. You know, we had...

He sadly passed away, but Ivan Bart, who founded, know, who was like the head of IMG, all these huge decision makers, because let's say Carolina Herrera was doing the talk or Wes Gordon was doing the talk, then every one of their friends would be in the audience. So, you know, I was by far the youngest person in the room at the time and I did whatever I could to meet everyone. And I actually eventually through going to those things, I built up a good network where then I actually started working close with her and her team, helping with social media.

where we then launched $10 student tickets to make it more accessible to students. But just finding those events where it's not maybe the most cool and flashy, like you're not walking down SoHo, you see like a party inside of SoHo, like, oh, I wanna be in there. Of course I wanna be in there. But this was kind of that really established generation of the fashion industry with some of these names that maybe a lot of people our age wouldn't know, but are really, have had these incredible careers. So just finding those spaces where those people are gonna be at.

That's kind of how I got started and it kind of all snowballed from there. That's really smart and that type of like grind and hustle is really, think what it takes when you want to build something yourself. Walk me through, I mean, because the type of confidence it takes to walk up to people at those events like isn't easy. Walk me through.

Josh Felgoise (22:32.61)

how you build up the confidence to walk up to those people and what you said and how you introduced yourself and how you positioned yourself. Yeah. Well, I think in like a lot of these events, going back to those, you know, fashion icon talks is you're in a kind of like old school auditorium. is, you know, folding chairs, whatever. It's not a pretentious, glamorous space, really. So it's, know, you're in room with maximum 100 other people and everyone is there seeing their friends. So it's almost like

It's not like they're guards down, but they're in a very comfortable environment where it's not like, they're not worried about seeing every single editor or running to a show right after. It's really, you it was kind of the social club where everyone was getting dinner right after, but a good place to see all these kind of like OG fashion icons. like, I feel like in those spaces, it was almost easy because everyone was really approachable and everyone was there to support whoever was on stage and you know.

to support their storied career. So I think in that realm, was really, know, also my whole thing and kind of how I go about, you know, the fashion industry or any creative industry in general is nobody's coming to find your work. You can be the most, you know, what I learned at art school is you can be at some incredibly talented students surrounding me, but you know, is you can be the most talented person ever, most incredible painter, most incredible designer, but if you don't put your work out there,

you're not showing it off or marketing yourself, nobody's coming to find you. So it's really sad because a lot of the most talented people I've ever met, they don't really have that drive for the business side or they don't want to put their work out there. Just un-private your Instagram, put it out there because I think once you get past that point is nobody's coming to find you, nobody.

you know, knows who you are, you really have to put yourself out there if you want to be seen or if you want to, you know, grow your network. I think that's kind of, you just have to get over that kind of scary leap of, you know, if I want to be in this industry, if I want to do well, it's really just on you. You know, I didn't come from a family that worked in fashion or film or, you know, or have any of those friends in those spaces. So it's kind of, you know, my mom's school teacher, you know, it's, it's, you have to do the work because

Josh Felgoise (24:55.982)

No one's going to do it for you. I love that piece of advice. Nobody's coming to find you and nobody's coming to find your work. I completely agree with you. And if you want to be found, you want to be seen, you have to put yourself out there and get over that feeling. Yeah. Do you have anything? Something else? Yeah. Just like totally. Just put your ideas out there. It could even be for like all these things. Like I was cold DMing like 40 brands a day during COVID just to pitch all these ideas. And that's when I like 19,000 followers and

2,000 followers on Instagram, but it's just all about positioning yourself because if you have the right idea, people will listen and also, know, you know, whether that's you want to start like your own TikTok channel or pitch a TV show or something like that, you might not have the budget or expertise right now to do it in the exact right way. But if you just put yourself out there, then you start training and you're learning as you go. And, know, the most amazing things just start from, you know,

the scrappy way of doing things and you never know how that's gonna or who's gonna see it. When you were in that time, the 19,000 followers, mean, compared to the really kind of massive following you have now, how did you, were you just sending like 40 messages a day, like spending your day being, and like, how did you deal with the rejection at that time? Like when you weren't receiving a lot of responses back, how did you kind of keep pushing through? There's no rejection really, because it's with the cold email, with the cold DM.

You know, let's say I, you know, there was a point during COVID where was like, I'm 40 a day trying to get as much as I can out there. And I still try to do as much cold outreach as I can. I even have a manager still, but it's like, no one's doing all the work for you. You got to rely on yourself a little bit. And I love the strategy backend side, but my whole thing is, know, if I email 20 people and I get one response for a Zoom, that's a win. You know, it's not about, you know, it's...

If I email two people and nobody responds, I mean, that's okay, but it's like, it's this whole industry, everything's a numbers game. So the more, more people you reach out to, you never know who's gonna kind of bite. And also let's say, you know, I email 40 people and then one of those turns into a really cool project and I get no responses from everyone else or even just like a no from everyone else. A no is not like a end of the world thing. It's just no with those brands. It's like.

Josh Felgoise (27:17.558)

either, you everyone has their own schedule. So it's all of this is a timing thing really. And then, you know, I, you know, down the line after the see you working with other brands, it might be a yes in the future from them. So it's, you know, it's not rejection really, because it's there's no harm in just asking. Absolutely. I completely agree with you. And the only harm is not asking, right? Like the only the only downside is not putting yourself out there. Now that you have amassed a following.

You said you keep you're still sending messages out and stuff like how are you continuing to maintain that scrappiness like and will you continue to do that for as long as you as long as you do this? Always, always just because you you work for yourself. So if you're not putting in the work, I mean it's you're leaving so much on the table and also, you know with the uncertainty of everything always in you know, the fashion industry, the creative industry, just in the world in general right now.

you gotta be scrappy. it's like, it's also, you know, I could sit back and wait for brand deals and things just to come to my inbox. But you know, everything that I'm passionate about and most of the projects that I'm really passionate about and excited about and really exciting partnerships I have are all from me reaching out and starting that because you know, if you're pitching to these brands and you're coming with a full-fledged idea and you know, all this excitement.

they're much more willing to work with you because you know, my whole thing is you know, in the influencer world, like I never want to be doing those fit checks. You know, lot of brands will still send me, here's three outfits, make a video about them, talk about them. But you know, what is the next step? You know, social media for me has never been the end goal. It has been the jumping off point to build a platform so I can do, you know, whatever I want or move into whatever industry I want to. So it's more of a, it is a case study and it's something I'm really passionate about, but.

You know, what is, you know, the next step from here? How do we make these partnerships more impactful? Even something I posted recently, I did a, you know, Seinfeld character breakdown. And that's something that me and a manager at my agency pitched. And, you know, it's just like all these ideas. And that was like a thing we pitched up to them and not content they've ever really done before. And I mean that, you know, got 150,000 views for a post with, you know, the partnership add on, which is kind of like,

Josh Felgoise (29:41.868)

an anomaly for this, it shows what really unique partnerships can do. Even I'm doing something with Dove Men's Plus Care right now. And how exciting can you make body wash? But what we're gonna do is I'm gonna sew a jacket based off the scent. the body wash can do something where you're adding that little extra excitement or something a little bit cool because everyone can do social media, but you have to have your angle so you can stand out.

You know, there is everyone's like this industry so over saturated. I'm like, there's a lot of people doing it. But if you have your own unique voice, then you know, you're not really competing with other people and there's space for everyone to succeed. You know, that's my favorite thing is, you know, I love whether that's putting my friends on with brands, bringing them to events and stuff like that is, know, everyone, you know, even if I have 10 menswear guys, influencers in a room with me, we all have such different voices and it's more fun to do these projects, be at these events.

with your friends, so you just want everyone to do well, because you want everyone to succeed, because nobody's stepping on anyone else's toes, because everything we do is we're hitting different types of messaging for these brands, and they're looking for all of that. Yeah, I also love what you just said about it's not over-saturated if you have a unique voice or a unique perspective. Like, nothing is too over-saturated. There is no market or no place that...

you can't kind of come into and make noise and break through like if you have that unique kind of selling proposition because that's true. How do you think social media has changed the way guys think about fashion? Well, you definitely see kind of this, you know, mass style shifts on social media. mean, if you look at the kind of like the L.A. fashion scene right now, the baggy, salvaged denim.

cropped small blank tees and all this, you know, I think it actually has done a lot of harm to kind of finding your own personal style, but also at the same time, it has opened up a lot of these kind of areas of style and stuff to the masses, which I think is, you know, making a lot of things a little bit more accessible. Because even, you know, I'm a huge fashion history nut. So, but like that's, you know, just me. So I'll actively go out and try to find, you know,

Josh Felgoise (32:05.858)

these style stories, these different generations of fashion. But you know, if I can just look up, you know, you watch Peaky Blinders, you like that style, but you don't really know anything about it. And if you could just type in ascendance and just start learning about it, I mean, that's pretty, pretty cool. Instead of having to go to, you know, the library and check out a book on 1930s men's fashion and, you know, peel through like, there's some great style history and fashion textbooks out there. But also like a lot of those books, if you want to buy them, are ridiculously expensive.

So I think it's done really amazing things for kind of broadening your concept of style, but also at the same time, things like all these influencer brands coming up that, in general, I'm a fashion designer at heart. There's a reason I haven't started a brand yet, because solely we just don't need more brand. We don't need more clothing. There's so much incredible stuff already being made, and that already has been made. You just have to find it.

It's amazing because it has, you know, opened up the kind of gates for a lot of people to explore these avenues. But at the same time, I mean, it's, know, with a tick tock shop and all these, you know, fast fashion brands kind of really like kind of abusing these platforms. It has caused a lot of harm as well. Speaking of the history of fashion, how has men's or guys relationship with fashion changed over the past decade? In your opinion? I think it's interesting. I mean, there's like

Two truths that are going on right now like it's either men are buying a lot more into the fast fashion and also at the same time men are looking to buy things that are a lot better made and will last longer. But I think it all you know it all depends on where you are and kind of what content you're picking up. You know I think you know we're finally moving back towards all these styles and know tailoring everything is cyclical. I think we're finally moving out of this.

Really terrible tailoring era where everything was shrunken and a little bit too tight, you know You know, I know we're seeing a lot of this, know 90s tailoring resurgence on the like the with these luxury brands But it's also you know, there's a lot of really good stuff even like if you look at suit supply in the past You know six plus years they started at out as the most, you know unstylish slim tailoring cropped pants

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that you can see and now they're, mean, if you look at the range of what they're doing, I mean, it's really incredible to see some of the styles they are coming out with. So I think, you know, once brands like that are picking up on like, this era of good tailoring is coming up, everything's like a whole lot more exciting right now, I think. You know, we're finally moving back towards things that are fitting well. And also hopefully, I'm just hoping we stop with this kind of like over consumption thing, but.

We'll see, because there's also the whole side of shopping. Just because you're shopping secondhand doesn't mean you're shopping sustainably. So there's also some, think Elliott Dupree made a really good video on that recently that I highly recommend checking out. But I mean, I'm sadly the wrong person to be asking about for some of these trends right now. Better than me, I'm loving, I've always loved the boat too. I think it's got a terrible rep throughout the years.

You know, not everything has to be super, super preppy and everything. There's a lot of amazing bo-choos out there. So I'm always excited to rock those. And then what else right now? I love seeing a lot of these kind of like brands re-embracing the kind of like wider lapels. So that's really, really fun for me. And then I'm trying to think.

I don't know, I'm really not good with trends solely because I don't wear a lot of super modern, modern things. I love everything going on with, as we've seen throughout the years, this Western wear resurgence and stuff like that, even more like a cowboy Western yoke on a shirt, pearl snap button ups, things like that I really, really love. I love all these styles, subcultures, and all these things that were made for...

practicality first and for a very specific task kind of being, you know, blown up for the masses. I think that's really cool as well. For somebody that doesn't know where to start with like dressing. I want to ask about a season specifically. Like what do you recommend guys wear this summer? Always. I mean, always, always, always linen button downs. You know, I think there's something beautiful in a kind of like scrunched up kind of wrinkled, you know, oversized button down.

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You know, everyone needs just a plain crisp white tee. I think is really really great. I'm honestly Such a fall winter dresser. So I will literally dress I'll wear denim Cordura I'll be wearing wool year-round but you know also just a linen unstructured blazer beat the hell out of it I mean, there's nothing cooler than I have a few really really great like destroyed You know, there's you know, everything is kind of you know fraying on it linen blazers that I love wearing

But yeah, I think there's so many different things that I recommend for this summer season. I'm doing a video with Banana Republic, but stripes, just wear stripes. Stripes make everything a little bit more fun in my opinion. And then if you are going a little bit more formal or something, a knit tie is like the coolest accessory. I'm always so excited to start wearing them when it gets nice out. And then now that you said fall, I'm not trying to jump ahead because the season is just starting, but what do you recommend a guy wears in the fall?

Everyone needs some corduroy. I love fall because I love textures and I love layering. Everyone needs to stop with those short overcoats and get something a little bit longer, a little bit more commanding. love a big overcoat can make any outfit much cooler. And just play around with fabrics. I mean, love moleskin. I love corduroy. I love some tweeds and different types of knitwear like cable knits. But anything that adds texture to an outfit, I couldn't recommend more.

I want to ask you a couple of specific like situations of what what to wear. So what do you recommend a guy wears on a date? I mean, very much depends where you're at. I think like a good pair of jeans fits for like any occasion. You know, either do that with, you know, a leather derby or a good loafer. A great way to spice up any outfit is fun colored socks. I'm most days wearing bright orange socks.

Bright red socks or honestly maroon socks in my opinion truly go with any single outfit But you know a fun color sock can honestly make any outfit much much more fun And for like fall winter just a good sweater or like a more casual, know button-up and then some type of like light jacket Or if it's in the summer I mean, I love a good like rugby like long-sleeve like polo rugby's are great because they're you know

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a little bit more casual, a little bit more fun, but also, you know, there's some good like weight and boxiness to them. Do you have like color recommendations? Like what colors are like the best for like the the lightweight jacket or any of that stuff? I mean, everyone needs like a good like kind of like, you know, more beige jacket. I love, you know, anything dark forest green in the fall, forest green, brown, all of that. I really, really love.

In the summer, my favorite colors actually are like a tobacco brown, like a tobacco brown, like linen blazer or shirt or something is one of my favorite things you can wear. And then anything sage green. I'm always excited to bring out some like nice sage green during the summer. What about what to wear on the first day of work? It totally depends because I know there are some weird unwritten rules that all these different like finance jobs and banks and

You know, that's a really hard one to say just because like it totally depends on what you are doing. I always have to say, you know, Oxford cloth button down, some type of, you know, like a worsted wool jacket or full, you know, if you're going full suit, you can go full suit. But I also love suit separates as well because it might feel like a little bit more approachable, like a good player, like pleated trousers, some type of, you know,

nice wool jacket and then an Oxford cloth button down either open if you don't want to wear a tie but it really I mean it's so job and company dependent because I was like I've talked with so many finance guys and you know help style them but there are so many of these weird like unwritten rules where it's like you have to stand you know you really don't want to stand out in some places some places you do you don't want to dress in a full suit because you know you don't want to look more put together in the body it's just so it's so odd

Wait, what do mean when you say you've helped some finance guys figure out their style? What do you mean by that? I have so many people hitting me up to kind of help them in their tailoring journey, whether it's my friends, my sister's friends, or just random mutuals online. I've helped a lot of people in their bespoke tailoring process finding the right suit for their wedding or for their job. I'm definitely not a stylist. I truly can't dress.

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other people than myself, but I've found some for the right for the right things. I could be semi helpful. No, I like that. I think that's I think like any guy would take something away from that. How about like where someone should go shopping for a work outfit? Like if they're just graduating, just starting a job, where should they go?

I mean, know, J-Press is a classic Ivy American icon. You know, get a good shaggy dog sweater with like a brushed wool. They're some of the best sweaters ever made. They have great shirts, great trousers. mean, Banana Republic and J. Crew are really killing it now. I couldn't, know, everything from very casual stuff to full suits, you know, the Ludlow suit at J. Crew is like...

Arguably it's a huge icon. mean Todd Snyder. I'm pretty sure that was his invention when he was at J. Crew But you know any any of those those major brands too are a great place to start and also It's not what it used to be. Sadly, it's you know, the oldest continuously running brand clothing brand in the US Brooks Brothers Once in a while they have these crazy sales. It's like three shirts for like 150 bucks or something But keep checking for that because you can get some really good deals and I still make some really amazing shirts

Whose style inspires you? Like who do you look up to for their style and for inspiration? It's really hard because there's a lot of people I look to as like I think they're incredibly stylish. But like my style, I'm very set in my ways about what I dress right now too. But I think, you know, some of the best dressed men in the world, know, Ethan Wong, he's based in LA. He's one of the most stylish people ever. There's this other guy, his username is Urban Composition, Peter Zatolo, who's

He's the epitome of the most like stylish, well put together man. Because there's also so many people, you I love stylistically that I know it wouldn't work on myself. You know, I think, you know, my friend Elliot wears some really funky cool stuff and I couldn't pull off half of it. But yeah, I I think for style inspiration, you know, I usually don't look towards a lot of people or movies. It's mainly just like old photographs because I like collect a lot of old, you know, black and white photographs. So it's more so.

Josh Felgoise (43:33.302)

old, you know, people attending old events and stuff like that. That's kind of where I, I look to. What is like an item or a piece of clothing that you'll never get rid of? I mean, there's a lot, like I have a few pairs of these custom work boots that I wear about every day, but it's all, you know, handmade lasts to fit your shoe, like your foot. And those will last me forever. You know, I'm wearing a pair of, you know, 1960s, know, biggie, salvage Levi's right now that are just perfection. And, know,

you know, the crotch and there's things that'll like blow out on these and I'll just keep mending them. So I have a few things like that. And then I a few like vintage items, some like beautiful like hand-knit sweaters from like the 40s, some good like, I'm a big collector of like 1920s to 1940s tailoring, so I have some great, you know, old handmade suits that I, even if they don't fit me, I'll just, as a reference item, I can't get rid of. What is one thing you wish every guy knew about menswear and style?

Ooh, that's a tough one. really think everything, you know, as we started this podcast with is everything comes down to the fit. It doesn't matter where you're buying your clothes from. It doesn't matter, you know, if you know all these style rules, if you're spending $2,000 an outfit or, you know, $120 on an outfit is, you know, a nicely fitting shirt where the shirt sleeves are the correct length with a jacket where the shirt sleeves...

are a little bit shorter than the short shirts you see like where everything is just kind of balanced, know, a well balanced outfit can, you know, I'm not, I hate like the idea of like commanding a room or whatever, but like, we'll just make you feel better too, you know, there's like, I can see, you know, you can be shopping at Charles Turwitt or something, which is, know, a lot of these finance guys shop at, which is a, you know, a good entry level price point.

And you know, it's the stuff, or you shop at men's warehouse and it doesn't matter, but if like a shirt fits you well, the pants sit nicely, you will look great. You know, that's the thing is I never, you never want to shame people or tell people like, don't shop here, you shouldn't do this because if it fits well, like I have a suit that men's warehouse made me actually this year. And it's, they launched a program where it's, you know, my bar mitzvah suit was men's warehouse. It was not a good suit, but they launched a program where it's, know,

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sub $1,000 made in the US, you know, made to measure suit from like reputable fabric from reputable mills. And the person that fit me for that suit knew what they were doing. And it is a nice fitting suit. Like I've truly no issues with it. Am I gonna be wearing it all the time? No, but that's just because I'm absolutely crazy and I own way too many suits. But I mean, it doesn't matter where you're shopping from. If something fits well, it fits well. I think that's really, really good advice.

Can you tell me about an interaction you've had over these past couple years of starting your own thing and becoming a creator that has really stuck with you, whether it's with somebody in the fashion industry or another guy in the space that you've met, somebody that's really, yeah. I mean, I've had so many amazing friends that I've made throughout the year. It's been a really good community builder for me.

And you know, I've had a few like made it moments, know, I'm the biggest, you know, vintage Ralph Lauren collector, just fan of Ralph Lauren in general, as you know, why it kind of started fashion. And you know, before I ever worked with the brand, I probably made 80 plus organic videos just talking about the brand history, my love of the brand and everything. And you know, the first time the company approached me to do a project with them, I don't think I've ever been like happier because that was like the like, if you really put in the work.

and position yourself well, you never know what's gonna happen. So like, mean, that was a really special moment for me. was the first time working with that team. But then it's also just like so many of the friends that I've made, know, like I, you know, and just adding this community to my life, I don't think there's anything more like, I can't be more grateful for anything than, you know, the community that it's brought and, you know, the kind of social life that it's brought has been really...

amazing for me because I never really wanted to be that like an influencer or content creator or anything, but I've met some really amazing people that also are like me where it's like, you know, they're doing this right now, but they all have a lot of bigger aspirations and really incredible ideas and are using this as their jumping off point. So, you know, I'm really, it's fun to meet like-minded people in that realm. Yeah, that is really cool.

Josh Felgoise (48:04.438)

Is there anything that surprised you about this kind of career or now that you've learned a lot more about the fashion space? Is there anything that's kind of shocked you or surprised, disappointed, anything like that? I mean, there are definitely some characters in this industry, which I quickly learned. But it's also, know, I think a lot of people are like really competitive for for not not not a whole lot of reasons. As I was talking earlier, I mean, you know, if there are 20 menswear influencers at an event or something, everyone's bringing their own thing to the table. Everyone checks off.

a different box for a brand's list. you know, I think a lot of people need to be like a little bit more open and welcoming to be like, yeah, wouldn't I want more people that I know at this event or on this trip or on this campaign because, know, or like, you know, if I'm getting something from a brand, but I have a friend who I think is like would do a crazy good job with it, I'm going to refer them to my friend. You know, it's I think there needs to be more of, know, everyone can succeed mentality than, know, it's me against everyone.

And I've always kind of been like that because you you want nice, hardworking people to do well. So I think, you know, that's something I'd love to see more. And I'd love to see brands, you know, actually leading on the crater a little bit more to, you know, for their ideas instead of just, you know, they give you a very structured brief and you have to do this. But it would I would love for more of the pitching from the ground up, because that's what I love to do. Is there anything from?

the brand side, because now that you've kind of peeled the curtain back into this industry and you were this kind of young, naive kid, really excited about meeting all these people and getting into the room, once you are in the room, is there anything that's kind of let you down or has changed your perspective about this world? I mean, it is interesting. I think there's a lot of

A lot of things have kind of let me down in this space too because you realize like lot of the, like not a lot, but there are some people at these brands that you're so ridiculously passionate about that are there or whether that's on the PR side or the brand side or something that don't really care too much about the projects or the brands. I'm very, I care about every project that I take on. Some things I'll have to do a little bit more for, I want to pay my rent or some of them are even more passionate about, but there's no project I won't give.

Josh Felgoise (50:27.438)

100 % because you know my whole thing is you know if a brand is paying you X amount of money to do something you want to give them the best you know product you can because then hopefully they'll come back so you know it's Sometimes a little hard because you see there are there are some people that you know Don't put in a lot of effort and have a huge payoff from it And there are a lot of people that put in so much so much so much work. I mean there are so many incredible accounts that I follow

These people that have 5,000 followers that are putting out the most insanely informative videos that I really love, but the brands just won't notice that because they're only looking for, they're plugging in their software. New York City, 100,000 plus followers. And I'm like, it'd be really nice if brands were actually looking for the right people instead of the biggest people. Yeah, I think that's exactly in line with what I was thinking too.

And then on the other side of it, there anything that once you were in the room that surprised you in a good way that you were really excited about that kind of invigorated or reignited your spirit around all of this? Yeah, I think a lot of people are much more approachable than I thought they would be. I still have those moments where I'm like, oh, I'm scared to talk to them because I've seen their face online so much. But everyone has been honestly a lot more approachable and almost more normal than you would think they were because there's a lot of characters and stuff you have to realize.

A lot of these people are seeing online are a lot more strategic than you might think. know, everything is very thought out, even if it's just like a silly little video where it's like, they're all putting on these characters and they're all just, a lot of them are just very normal people in real life. So that's been kind of fun to kind of peel back the curtain and see that. But yeah, no, I think that's a, I think that's a good example, honestly. Yeah. And then is there anything else that like you could tell us about the

New York kind of city creator fashion space that like we wouldn't know from just watching you guys. That's a tough one because like I'm such in a little corner of the menswear space. mean moving into kind of like the women's fashion space is just a huge, huge pool of people that I just do not really know. I mean in the men's world there's you know probably like around 40 people that really are

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you know, doing this like, well, there's more, but in like kind of more like the classic menswear space, there's probably about like 40 people that I regularly see at these events and everything. But I think it's really fun. I think like a lot of people like wouldn't know about like a lot of these guys are, you know, meeting up and like filming each other's content just to help out other people too, which is really nice, you know, instead of, you know,

because not everyone, like I'm not spending $1,000 on a videographer for every single reel. There are people that spend thousands of dollars to create each video, but it's really nice when, you know, there are a lot of people that are just like helping out a friend because then they'll film their stuff after. But also it would be really nice, but there's a lot of people who are really talented and have a lot of other passions that just don't show that online because that's not the image they're portraying, but.

I mean, think the world would be very surprised by a lot of how talented some of these people are in the city. Yeah, absolutely. And then you make a lot of videos about like the history of fashion and all of those. I really love all those videos you do. What is like a fun fact that you could share about the history of fashion or the past decades about fashion that guys wouldn't know? that's a tough one. I mean, honestly, just like everything in design right now, like nothing is new. Like that's the biggest thing to like.

that I try to tell everyone, nobody's really inventing anything new in men's work or in fashion. It's all been done. It's all just like a different reference or iteration of something that's been around for decades. So, you know, that's my major takeaway is, you know, everything you're seeing right now, if it's just like a normal jacket or something, you know, every single little detail at the start was not designed for...

style purposes, a lot of it was designed for a specific use. Whether that's on a suit jacket where there's a center vent in the back, that was mainly for equestrians. If you're riding a horse and something like that, everything was made for a specific purpose and then it became stylish. And that's what I kind of love is a lot of what I love about fashion, it was born from a place of practicality and then people figured out how to make it cool. And that's really like, that's one of my biggest takeaways.

Josh Felgoise (55:03.426)

That is really cool and I liked what you said a lot about it being cyclical and like things come back in style again and again. I liked a lot of what you just said there. And then my last question for you is what is your advice to your younger self? My one thing is in this industry, especially in New York, know, cost of living, everything, you know, there are so many distractions. I mean, even just surviving month to month out here can be a little bit of a chore and can get really overwhelming. You can get distracted by all these events is

stick to making things. Right now, I'm in kind of this position where it's how do I continue to do what I'm doing but also make things that feel like maybe a little bit more fulfilling. So getting back to sewing and all these things that are fun creatively, you're trained to and you love doing, but also act as, they're your therapy. just because something's bringing a check or seems like could lead to something good is just focus in on.

Genuinely just what makes you happy. There are so many distractions in New York So I'd say, know, just keep making things not everything, you know All my creative energy is forced into making little videos right now Keep sewing like I'm sitting next to my industrial sewing machine right now that and I've barely used this year So it's you know Staying staying close to the roots of why I started all this I love that and I think there's this side of like

outside of your creativity that other thing that you you do that actually inspires and kind of reinvigorates the other part of the creativity too. I think that's really cool. Well I think people are gonna have a really awesome takeaways from this episode and I think you shared a lot of really great insights into menswear and men's fashion and style that I didn't know before and I think people will take a lot away from this. So thank you so much for the time today. Where can everybody find you online.

look up Simon Gold on Instagram and Tik Tok and I should pop up and yeah, thank you so much. This was really fun. Really good questions, by the way. loved, I love this. was fun. Thank you. Is there anything else that I missed that you wanted to share? I think that's really it. I mean, this is second podcast I've ever done and this is, this was a by far the most easy, easy one. I've, this was fun. This is good. I really, I really appreciate that. Thank you so much and we will, we'll be in touch soon again.

Josh Felgoise (57:17.844)

That is the episode. Thank you so much. Listen, I said a guy's guide to what should be talked about. I'm Josh. I'm 25 years old and I'm here every single week, every single Tuesday to talk about what should we talked about for guys in their twenties. If you liked this episode, I really hope you did. Please like subscribe to this podcast. Five stars in for that's one, two, three, four, five stars, not four and three, two and one, five stars. Thank you so much. I really, really appreciate that. If you're top of that, should we talk to our guys? They're 20 cents. My email or my DMs is that the guy set thgguiset on Instagram, tick tock, all social media platforms or to my email. It's josh at guyset.com. J O S H at guiset.com.

And I will be sure to talk about it. You can also know my website guyset.com G U I S E T.com to leave a comment questions, anything right there. There's a box. You can also check out other blog posts on there. There's a lot of other stuff on there. Thank you so much listening to guys set a guy's guide to what should be talked about. And I will see you guys next Tuesday. See you guys.