#106 - How To Find Your Style with Simon Goldman
Jun 10, 2025
Simon Goldman, a 24-year-old menswear designer and content creator, is here to share his style advice, brand recommendations, and summer fashion tips. He talks about his journey from sneaking into NYC fashion events as a student to building a massive following of over 500k across social media. He reveals the biggest mistake guys make when getting dressed (hint: it's all about fit), breaks down his essential 5-piece wardrobe formula, and explains his "buy once, buy well" philosophy.
From sending 40 cold emails daily to networking with fashion legends, Simon discusses the hustle required to break into any industry. He also covers practical style advice, the best brands for different budgets, why thrift shopping is a goldmine, and seasonal fashion tips.
Whether you're looking to upgrade your style or learn how to put yourself out there professionally, this conversation is packed with actionable insights.
Topics discussed:
The 5 essential wardrobe pieces every man needs
How to find your perfect fit
Best brands for any budget
Networking and cold outreach strategies
Building confidence through style
More: From Fashion School to Social Media Success: Menswear Designer Simon Goldman's Guide to Building Your Personal Style
A 24-year-old menswear designer and content creator shares his journey from struggling fashion student to successful influencer, plus his essential tips for men's style.
When Simon Goldman started fashion school, he couldn't find answers to basic questions about building a portfolio or navigating the creative industry. Fast-forward a few years, and the 24-year-old Chicago native has built a thriving career as a menswear designer, pattern maker, and social media content creator in New York City.
In a recent interview, Goldman shared his unconventional path to success, his philosophy on men's style, and practical advice for guys looking to upgrade their wardrobes.
The Foundation: Why Fit Trumps Everything Else
The biggest mistake men make with their style? Poor fit.
"It all comes down to fit," Goldman explains. "Even if you're just a finance bro going around, the 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."
His advice is refreshingly practical: avoid pants that taper too aggressively at the ankle, which creates an unflattering "carrot-shaped" silhouette. Instead, look for trousers that have room in the thigh and a subtle taper from the knee down.
Goldman's golden rule: "A well-balanced outfit can make you feel better. You can be shopping at Charles Tyrwhitt or Men's Wearhouse—it doesn't matter, but if a shirt fits you well and the pants sit nicely, you will look great."
Building Your First Wardrobe: The Essential Five
For men starting from scratch, Goldman recommends focusing on these five foundational pieces:
Leather derbies - "A good derby can be worn with jeans or suit trousers"
Well-fitting trousers - Either flat front or pleated, depending on your preference
Dark wash denim - A versatile foundation for casual looks
Blank tees - Goldman prefers black and white basics over graphic tees
Oxford cloth button-down - "There's no more versatile shirt ever made"
Pro tip: Add an unstructured, unlined blazer to easily dress up any casual outfit.
Where to Shop: Quality Over Brand Names
Goldman's approach to shopping is refreshingly democratic. While he loves heritage brands like Buck Mason and Natalino for their quality and style inspiration, he emphasizes that great style doesn't require a massive budget.
Recommended Starting Points:
Buck Mason - "Phenomenal brand" with excellent silhouettes and some made-in-USA pieces
Natalino - London-based brand offering everything from sweaters to suits with "really good style inspiration"
J.Crew and Banana Republic - "Really killing it now" for everything from casual to formal wear
J.Press - Classic American ivy style, famous for their "shaggy dog" sweaters
The Scrappy Approach:
Thrift stores and consignment shops
Flea markets
Online platforms like Depop and The RealReal for vintage finds
Housing Works (for New Yorkers)
"You can find some really fantastic deals for the brands that those platforms are not advertising to," Goldman notes.
Seasonal Style: What to Wear When
Summer Essentials:
Linen button-downs - "Something beautiful in a scrunched up, wrinkled, oversized button down"
Crisp white tees
Unstructured linen blazers - Even better when they're "beat the hell up"
Stripes - "Make everything a little bit more fun"
Knit ties - Goldman's favorite warm-weather accessory
Fall Favorites:
Corduroy - "Everyone needs some corduroy"
Longer overcoats - "Stop with those short overcoats and get something a little bit more commanding"
Textured fabrics - Moleskin, tweeds, and cable knits
Forest green and tobacco brown - Goldman's go-to fall colors
The Power of Details
Sometimes the smallest changes make the biggest impact. Goldman's secret weapon? Colorful socks.
"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—they truly go with any single outfit."
Building Confidence Through Style
Growing up as "a little chubby" kid, Goldman learned early that dressing well could boost confidence. His approach evolved from wearing fedoras and fake glasses to emulate musicians like Roy Orbison and Buddy Holly to developing his current "uniform" style.
"I am pretty much a uniform dresser," he admits. "I'm always in a good pair of really worn-in jeans, good work boots or beat-up Alden Oxfords, either a t-shirt, button-down, an old tie, and some type of jacket or blazer."
The Entrepreneurial Mindset: Building a Career in Fashion
Goldman's journey from fashion student to successful content creator offers valuable lessons for anyone looking to build their own path:
The Power of Cold Outreach:
During COVID, Goldman sent "40 cold emails a day" to brands and industry professionals. His philosophy: "If I email 20 people and I get one response for a Zoom, that's a win."
Finding the Right Rooms:
Instead of chasing trendy events, Goldman sought out established industry spaces like the 92nd Street Y's fashion icon talks, where he could meet decision-makers in a more intimate setting.
The Reality Check:
"Nobody's coming to find your work," Goldman emphasizes. "You can be the most talented person ever, but if you don't put your work out there, nobody's coming to find you."
Style Philosophy: Everything Old is New Again
As both a designer and fashion history enthusiast, Goldman offers this perspective: "Nothing is new in men's wear. It's all been done. Everything you're seeing right now is just a different reference or iteration of something that's been around for decades."
His advice: Focus on timeless principles rather than chasing trends. Build a wardrobe of well-fitting, quality pieces that work for your lifestyle.
Final Thoughts: Stay True to Your Creative Roots
For young creatives, Goldman's parting advice is to "stick to making things" despite the distractions of social media and industry pressures. "Not everything—all my creative energy is forced into making little videos right now. Keep sewing. Stay close to the roots of why I started all this."
Whether you're building your first professional wardrobe or refining your personal style, Goldman's approach proves that great menswear doesn't require breaking the bank—just understanding fit, focusing on quality over quantity, and staying true to what works for you.
Listen to the Full Episode: This article is based on Simon Goldman's appearance on the Guyset podcast with host Josh Felgoise. To hear the complete conversation, including more detailed discussions about fashion history, Goldman's networking strategies, and additional style advice, listen to the full episode on your preferred podcast platform.
Want more menswear advice and style tips? Follow Simon Goldman on Instagram and TikTok @SimonGold for daily style inspiration and fashion history insights.
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See you guys next Tuesday.
