What People Wear To Brimfield

Pre-Loved street style from the largest and oldest vintage market in the U.S.

May 22, 2025

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Picture this: Brimfield — where vintage fashion is an extreme sport and your outfit needs to survive three seasons, an ice cream cone melting down your arm, the occasional flash flood, treasure-hunting on your hands and knees, and 20,000+ steps.

All in one day.

For those uninitiated to the madness, Brimfield Flea Market is the largest and oldest outdoor vintage market in the U.S., featuring 21 sprawling fields across 100+ acres, 5,000+ dealers from around the globe, and endless treasures along one mile-long country road… or eccentric runway, depending on how you look at it!

Three times a year (May, July, September), this rural Massachusetts town is swarmed by us “flea people” and it totally transforms into — at once — a campground, industry event, state fair, and fashion epicenter.

I go full gonzo journalist at Brimfield, embedding myself in the dealer’s world Monday through Friday (the industry folks mostly take off before the weekend’s crowds get there…) and documenting every detail for Pre-Loved readers. From sunrise to dinner, I'm detailing the little moments that make Brimfield legendary.

Coming up: dealer deep dives, chit-chats with the most knowledgeable vintage-hunters in the world, the incredible stories behind the finds, and all the vintage lore your heart desires.

But today? We're doing style-spotting — that’s street style but country-gravel-road-vintage market version! Ever wondered what shoes survive sloshing through the fields? Which messenger bags the dealers use to tote their treasures? How people shield themselves from sun while still looking effortlessly cool? I've got answers.

Just because you’re digging in the $5 piles doesn’t mean you can’t pull an absolute ‘fit!

I saw people styling their creature comforts and camp-gear, turning practical get-ups into personal style statements. I clocked the DIY masterpieces, and documented those micro-style moments where an accent transforms utility into something vibrant and one’s own..

And I can’t wait to go back.

Below are a selection of style shots from Brimfield, May 2025:

Lexie Butterfly Vintage (top) sewed vintage gloves to her dress for the opening day of Hertan’s field.

Note on the weather: I'm a May devotee — supposedly the sweet spot for temperature (before the summer scorchers in July and September) and the most coveted finds (because dealers save their discoveries from over the winter for the opening of the new season).

Though the LL Bean Boat and Tote remains a Brimfield staple, the hot bag of the year was definitely the vintage newspaper messenger bag. Though my pals Nate and Andrea of To Hell and Back Vintage (third photo) say these bags hold less than you might think…

Pictured: Michelle of Allegra Vintij at Shelton’s field; incredible patched pants at Dealers’s Choice; Kaylee of Jive Finds shopping Heart-o-the-Mart wearing 69 Tearz senior cords; Madi of White Witch Vintage in the Mahogany Ridge Fashion Tent; and lastly — me!

As Beyonce said: “Denim on denim, on denim, on denim.” — followed by an incredible round-up of lace-up boots to close out this show…

I'm always hunting for more vintage market stories and style-spotting moments. Are there incredible outfits at your local flea? Let me know, and maybe Pre-Loved will dispatch near you!

And if this peek into Brimfield's fashion got you excited, subscribe today for more vintage adventures from the fields to come: