S9 Ep30 STYLEBIDDER: Ken Pickart, American Ivy enthusiast and menswear vintage dealer - on Brooks Brothers, and building a business with social media.

S9 Ep30 STYLEBIDDER: Ken Pickart, American Ivy enthusiast and menswear vintage dealer - on Brooks Brothers, and building a business with social media.

Author: Emily Stochl October 6, 2025 Duration: 50:33

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On today's show, we're chatting with Ken, the founder of Stylebidder, a secondhand shop specializing in vintage and designer menswear. Ken has been selling for over thirteen years, starting out on eBay and Grailed, and he eventually expanded to his own online store and pop-ups events across the northeast including Newport Folk Festival & Alfargo's Marketplace. 

Ken is a true Ivy style enthusiast with deep knowledge of American menswear history, including Brooks Brothers, and in 2024, Stylebidder began an ongoing collaboration with Brooks Brothers sourcing and cataloging vintage pieces from their 200 year history for their seasonal vintage shops.

He shares lessons learned from building his business, including: the power of sharing educational content on social media, navigating the balance between online sales and pop-up markets, and advice for working with consigners

Plus so much more. Let's dive right in!

DISCUSSED IN THE EPISODE:

  • [1:45] Ken's early style influences: from skateboarding to discovering American Ivy style in college
  • [5:09] Going to college in Boston, Ken found the thrift stores were a treasure trove for American Ivy style.
  • [7:20] He started selling part-time on eBay because he found s0 many good finds sourcing for himself, including five Hermès dress shirts at a thrift store
  • [9:30] Things really picked up when he started to take on clients to do consignment.
  • [12:47] The vintage scene in Vermont and building community with other dealers
  • [13:38] His first pop-up at Burlington Vintage Market and the transition from online-only selling
  • [17:23] Developing his vintage specialties of American Ivy menswear brands, tailoring, and Japanese designers
  • [20:15] What defines American Ivy style 
  • [27:27] On working with Brooks Brothers
  • [32:42] How social media, particularly educational content, has helped Stylebidder grow.
  • [37:32] How to strike work-life balance, including between online sales and pop-ups.
  • [41:17] Favorite pieces and personal style : picking through a hayloft, finding Big E Levi's, and hunting for the perfect tweed sport coat

EPISODE MENTIONS: 

LET'S CONNECT: 

SPECIAL THANKS: 

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Every week, Emily Stochl invites you into a conversation that goes far beyond the clothing rack. Pre-Loved Podcast with Emily Stochl is built on the idea that every second-hand garment has a past, and that exploring those histories makes our present style more meaningful. Rather than just offering shopping tips, each episode feels like sitting down with a fascinating friend who shares your passion for vintage, digging into the many layers of what it means to wear pre-owned fashion. You’ll hear from a diverse range of guests-from collectors and stylists to entrepreneurs and historians-as they explore not only personal style but also the practicalities of running a resale business, the complexities of the global second-hand market, and the environmental ethos behind choosing used over new. The heart of this podcast lives in those incredible stories: the serendipitous flea market find, the garment that carries a decade of memories, or the simple, powerful act of giving a piece a new life. Emily guides these discussions with genuine curiosity, making each topic accessible whether you're a seasoned thrifter or just curious about sustainable fashion. It’s a thoughtful, engaging look at how what we wear connects to culture, art, beauty, and the kind of mindful consumption that can reshape an industry. Tune in for a fresh perspective that celebrates the character, sustainability, and deep personal connection found in pre-loved fashion.
Author: Language: English Episodes: 100

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