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

Oct 6, 2025

Ask episode

Chapters

Transcript

Episode notes

This episode is brought to you by ThredUp —and big news: their tech just got a serious upgrade, go check it out! Plus, new customers get 50% off and free shipping when you use the code: PRELOVEDPOD.

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:

📸Instagram: @emilymstochl
🐦Threads: @emilymstochl
🎥TikTok: @emilymstochl
📧 Substack: https://prelovedpod.substack.com/
🎧Patreon: https://www.patreon.com/prelovedpod

SPECIAL THANKS:

A special thanks goes out to my Patron Insiders – your support makes Pre-Loved Podcast possible!

Patty Weber
Kathy Brand
Lisa of Queenie & Pearl
KT
Lydia Welp
Michael A.
Megan Morris
Jennifer
Alana Rivero
Jerrica Yasumura