What People Wore and Shopped at the Pickwick Vintage Show in Chicago
Plus 30+ vintage pieces, mostly under $150, and in sizes XS-XXL, inspired by the vibes!
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I spent last weekend shopping and style-spotting at Pickwick Vintage’s first-ever Chicago show. Pickwick Vintage — founded by Richard Wainwright of Arcade and A Current Affair — features top-notch vintage dealers who bring out the best vintage clothing, designer pieces, jewelry and handbags. It spans all eras: you’re just as likely to find Edwardian lawn dresses as you are Fendi Baguette bags. In general, though, it leans more true-vintage and designer fashions, as opposed to a denim-tees-and-workwear style show.
I went with my bestie, Gail of Found+Formed, and we met up with our Milwaukee-based pals, To Hell & Back, who were dealing. The show was on the eighth floor of the Chicago Athletic Association Hotel (great views of The Bean!) and they let us go up in small groups so the room felt full, but not crowded. The showroom had wood paneling, high ceilings and soaring stained glass windows — like the loveliest vintage fashion cathedral. The team behind these shows know how to curate a space and a vibe.
Right when we walked in, we ran into Ella from Thief Island, and flipping through her treasure trove booth — puddling 1920s lace gowns, circus and theater costumes, side-button pants, and colorful hand-knit sweaters — we knew immediately it was going to be a special kind of day.
When I’m at a vintage show, I’m people-watching as much as I’m booth-browsing. Here, I met several local Chicago stylists, but there were also lots of dealers and fashion folk from L.A. I heard from sellers that after the A Current Affair show in New York the previous weekend, some of the west coast dealers loaded their stuff on the Pickwick truck to pit-stop in Chicago before heading back home to California. One dealer even told me, “Ignore my ‘A Current Affair pricing’—we’ll do a Midwest market rate.” That’s hot!
Let’s talk The Looks. People get dressed for these shows — they’re fashion forward, and of course everyone pulls out their best statement vintage. So naturally, I had to take out my notebook for you all.
The most prevalent styling trend I saw was all the fur hats. Everywhere! We all know a lot of fashion media ink was spilled on fur coats last winter (“the mob wife trend”) but it wasn’t quite cold enough to pull those out yet. Instead, people were accessorizing with fur hats—both pillbox styles and large, fluffy statement pieces.
I also spotted lots of BODE-esque sweaters, statement coats of all kinds, and sculptural jewelry. And these were exactly the kinds of pieces dealers told me were flying fast — they seemed thrilled with the crowds and sales, bagging up statement sweaters and jackets for eager shoppers all day. We stayed from open-to-close, and rumor has it Pickwick will be back in Chicago this spring, so count me for more!
Me personally? I went home with a 1920s bias-cut emerald green velvet dress—extremely ‘Stevie Nicks-Florence Welch-coded’—with draping mutton sleeves and a plunging V-neck. It’s from one of my favorite Chicago shops, Knee Deep Vintage in the Pilsen neighborhood. Carlos picked it off the rack just for me, and when a vintage dealer asks you to try something on because they think it’ll really suit you, YOU DO IT. They’ve got the eye!
Funnily enough, when I got back to my desk on Monday morning, I found the year-end edition of the eBay Watchlist trend report in my inbox, and found it mirrored so much of the vintage trends I spotted at Pickwick: fuzzy mohair cardigans (up 22%) and statement jackets (up 31%). And as a devotee of my leather patchwork jacket (up 37%) and my 90s Coach bags (“shoppers searched for ‘Coach’ 92 times per minute on eBay this year”), I thought —okay, me and eBay and Pickwick, we’re on to something!
So, in this letter, I’ve included a selection of vintage street style inspiration from Chicago’s Pickwick Vintage Show, November 2025, plus 30+ vintage pieces, mostly under $150, and in sizes XS-XXL, inspired by the vibes. Enjoy!
