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In this episode, Tim sits down with Stephen, the founder of Classicfella, a men’s underwear brand rooted in tradition but updated for today’s discerning wearer. Based out of Atlanta and made in Italy, Classicfella takes iconic pieces like white briefs, tanks, and boxers and gives them a refined touch with high-quality fabrics and thoughtful design. Stephen shares the inspiration behind the brand—his transition into midlife, a desire for maturity in his wardrobe, and the gap he saw between basic bulk-store briefs and ultra-luxury options.

Listeners will learn about the design process, the importance of fabric and fit, and how feedback from customers is shaping the brand’s next evolution—including new sizing, updated materials, and tagless options. The conversation dives into design decisions like the importance of waistband aesthetics, the relevance of classic styles today, and why even a button-fly brief could have a comeback.

Classicfella isn’t just recreating the past—it’s reimagining it with purpose, quality, and authenticity.

Quotes to Share:

• “I reached an age where I looked at my underwear drawer and thought, ‘I don’t identify with any of this.’”


• “We’re not a white-labeled brand. Every element was custom cut and sewn in Italy for our customer.”


• “Classic doesn’t mean outdated. It means refined, elevated, and rooted in timeless design.”


• “Our core audience? Mid-20s to 50s professionals who want something better—but not flashy.”


• “Vanity sizing was something I didn’t expect, but now I understand it completely.”


• “The waistband isn’t just functional—it says something about you.”

Where to Shop:

Visit Classicfella.com (that’s fella with an “a”!) for timeless briefs, boxers, tanks, and more. Get 10% off your first order and volume discounts when you buy multiple pairs.

Links:

• Store –
  
  
  
  • https://www.rmac.store/TIM77812
  
  
  
  


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