#13 - Body Image and Fashion with Ryan Winter
Sep 5, 2023
Ryan Winter (aka Ryan Schumack) is a style and fashion TikToker, model, and owner of Sweet Bee cafe in Brooklyn. I’ve been following him on TikTok and Instagram for about a year now and think he's got a great sense of style so naturally he was one of the first people I had in mind when I created Guyset. We ended up talking about way more than fashion tips and got into a lot of the topics I really want to dive deeper into on this podcast including body image, fitness standards, workout routines, and eating disorders. Ryan was incredibly honest and willing to get into the topics that guys simply don’t talk about enough. We also talk about the modeling industry, style and fashion tips, skincare, shaving and so much more.
From Male Model to TikTok Success: Ryan's Honest Take on Body Image, Style, and Building Your Own Path
How a Minnesota model ditched traditional beauty standards, opened a Brooklyn café, and built a following by being authentically human
Ryan Winter's journey from modeling runways to creating viral TikTok content while running a Brooklyn café isn't your typical success story. At 30, he's built a following by being unapologetically real about topics most guys won't touch: body image struggles, eating disorders, and finding your authentic style.
His story offers powerful lessons for any guy in his twenties navigating the pressures of social media, dating, career uncertainty, and the constant comparison game.
The Modeling Reality Check: Beauty Standards Are BS
Ryan's modeling career started like many others—with compliments at malls and encouragement from his girlfriend. But moving to New York at 23 with $300 to his name gave him a brutal education in the industry's realities.
"When you're seeing those cool editorial photographs, you make nothing," Ryan explains. "You get paid like $500 to be in Vogue. The photos you see on websites with models wearing whatever—that's where you make money, but it's not glamorous."
The pressure to maintain a specific look led Ryan down a dark path. Despite being professionally successful (his abs graced Calvin Klein underwear boxes for three years), he developed an eating disorder.
"I had bulimia for a while. I was really sick and really unhealthy," he shares. "There was a correlation between my bulimia and drinking. When you're not eating, you barely drink and you're wasted. Then it's like, 'Well, I'm gonna throw up when I get home anyway.'"
The Lesson: The people who look "perfect" on the outside often struggle the most with body image. External validation doesn't fix internal issues.
Breaking the Body Image Cycle
Ryan's turning point came through understanding how addiction and eating disorders work in the brain. He discovered Michael Pollan's research showing that depression, anxiety, and eating disorders operate similarly—through "overactive neural pathways" that keep you fixated on one thing.
"Understanding that helped me give myself grace to be imperfect," Ryan says. "If I go out and eat too much and throw up, I'm disappointed, but I didn't fail. I fell victim to how my brain operates. I start again tomorrow."
His approach to recovery focused on:
Stopping alcohol for a year to break the cycle
Changing his relationship with food to something more sacred
Recognizing that food and sharing meals is about community, not just consumption
Accepting that setbacks are human, not personal failures
The Truth About Male Body Image: "It's harder for guys to talk about it. It's not as spoken about, but I think a lot of guys have an unhealthy relationship to fitness."
Style Wisdom: Feel First, Rules Second
Unlike most fashion influencers who push specific brands or trends, Ryan's style philosophy is refreshingly simple: start with feeling.
"Everything is kind of from a place of feeling. I never go into outfit creation knowing where it's gonna end up. I start with an item that I wanna wear and then I try on stuff until I find something I like."
Ryan's Style Essentials for Guys:
The Foundation:
Straight-fit jeans (he recommends Nudie Jeans "Tough Tony" or Gap's 90s loose fit)
Dress pants from thrift stores, tailored to fit ($7 pants + $30-40 tailoring = perfect trousers)
Basic tees and tank tops
First Date Formula:
Dress pants (not too formal)
Casual top (t-shirt or tank)
Light jacket or overshirt for layering
Hard-bottom shoes (boots or loafers)
Belt (doesn't have to perfectly match shoes)
Anti-Rules Approach:
"Don't pay that much attention to what's going on online"
"Listen to yourself before you listen to anyone else"
"Get your shit tailored—it makes all the difference"
The TikTok Transition: Building Community Through Vulnerability
Ryan started TikTok in 2021 as a marketing strategy for his café. What began as a business move became something deeper—a way to connect authentically with people struggling with similar issues.
"There's so much oversharing on social media platforms," he admits. "But I also want to share my experience so people know they're not alone when they're going through these experiences."
His content evolved from simple fashion videos to honest discussions about body image, relationships, and mental health—topics rarely addressed by male influencers.
Building a Business While Building Yourself
Sweet B Café in Brooklyn became Ryan's passion project during COVID. Starting with $300 and a dream, he found his business partner through an Instagram story asking for investors.
The café represents more than just a business—it's a community space that validates Ryan's belief that relationships matter more than appearance or social media metrics.
"When I'm on my deathbed, I'm never gonna look back and think 'thank God my body fat percentage was X at 25.' I'm gonna look back at the fun I had with friends, the experiences I had."
Dating Advice That Actually Makes Sense
When it comes to dating, Ryan's approach is surprisingly grounded:
"Go on a lot of dates and find out what you do and don't like. Learn—is this actually what I find sexy? Or is this what I think I should find attractive because of beauty standards?"
His biggest insight: Conventional beauty standards don't have to dictate who you're attracted to. Finding someone genuinely attractive to you is more important than meeting societal expectations.
Practical Grooming and Style Tips
Ryan keeps grooming simple but effective:
Skincare:
Basic moisturizer (Neutrogena or CeraVe)
SPF during the day
Under-eye cream as you get older
Grooming:
Harry's razors for shaving
Dove Men sensitive skin deodorant
Simple approach to everything
Cologne:
YSL (his daily driver for 10+ years)
Versace Dylan Blue for special occasions
The Mental Health Reality Check
Perhaps Ryan's most important message is about destigmatizing mental health discussions among men:
"We're all going to fall short of being the person we want to be. That doesn't make you a bad person. It makes you human."
His journey shows that:
Seeking help isn't weakness—it's necessary for growth
Perfect people on social media are often struggling the most
Community and relationships matter more than individual achievement
Recovery is ongoing, not a destination
The Bottom Line: Authenticity Over Everything
Ryan's success comes from being genuinely human in a space that often demands perfection. He's built a community by:
Sharing struggles openly and without seeking pity
Prioritizing real connections over follower counts
Building something tangible (the café) alongside digital presence
Staying true to his values even as trends change
For guys in their twenties, Ryan's story offers a different model of masculinity—one that embraces vulnerability, values mental health, and defines success by relationships and personal growth rather than traditional markers.
"No one makes content and is cool doing it," he laughs. "To always remind myself of that helps me not take it so seriously."
In a world obsessed with image, Ryan's authenticity stands out. He's proof that being genuinely yourself—flaws, struggles, and all—is not only okay but powerful.
Find Ryan on TikTok @youngfontina and Instagram @rswinter. Visit Sweet B Café in Brooklyn's Clinton Hill neighborhood. Subscribe to Guyset for more honest conversations about navigating your twenties as a guy.
I loved this conversation and I hope you do too! You can check out Ryan on Instagram @rswinter or on TikTok @yung_fontina.
Timestamps:
3:47 Interview starts
4:56 Why Ryan started on TikTok
13:22 How he started modeling
18:09 We talk about validation from modeling
21:12 We dive into the modeling industry
24:07 What he’s most proud of in his modeling career
From here on out we talk about body image, fitness standards, working out, and eating disorders until 58:48 (this is my favorite part of the podcast)
26:06 Working out and Ryan’s first few years in NYC
31:19 Body image/ eating disorders
44:52 We talk about alcohol
51 My commentary on this conversation for guys in their 20s
52 Body image and social media
54 We talk about working out and body image
58:48 His recommendations for what to wear going out
1:04 His jeans and pants recommendations
1:10 Mindset when buying new items
1:12 First date outfit recommendation
1:16 Cologne and deodorant recommendations
1:18 We talk skincare and shaving (your face and balls)
1:22 More fashion tips
1:23 We talk about his cafe in Brooklyn SweetBee
1:28 Ryan's dating advice
1:30 we talk about the conversation we just had and say goodbye
Send in any questions, things you want me to talk about, or things that should be talked about for guys in their 20s to josh@guyset.com
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See you next Tuesday.