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Chicago, Illinois
Chicagogo Vintage: Where to Find the Coziest Jackets in the Windy City

Buying vintage jackets can be like finding a needle in a haystack –; it’s easy to get lost in the clutter and forget why you started looking in the first place. But fear not, my fellow fashion aficionados, as I’ve rounded up the top 10 places in Chicago to score the coziest, most unique vintage jackets around. Whether you’re a fan of denim, faux fur, leather or bomber styles, these shops will have you covered in more ways than one.

    First on the list is Velvet Goldmine. Located in the Wicker Park neighborhood, this boutique offers a range of vintage leather and suede jackets from the ’60s to the ’90s, with prices averaging around $75.

    Next up is Lost Girls Vintage, which stocks a selection of rare and unusual finds sourced from all over the country. You’ll find everything from ’80s ski jackets to ’60s mod coats at this West Town shop, with prices ranging from $55 to $175.

    For those seeking out the perfect denim jacket, look no further than Kokorokoko Vintage in Logan Square. This colorful store carries a variety of denim styles from the ’70s and ’80s, as well as bomber jackets and military surplus pieces for an edgy, retro aesthetic. Prices start at around $50.

    Another great spot for denim lovers is Dovetail Chicago. Located in Lincoln Square, this shop specializes in vintage Levi’s jackets and other denim garments, with prices averaging around $85.

    Moving on to the North Side, Vintage Quest offers a wide variety of retro jackets from all eras, with silk bombers, leather moto jackets, and wool pea coats on the shelves. Prices range from $50 to $150 depending on the style.

    If you’re looking for something truly unique, head to Knee Deep Vintage in the Ukrainian Village. This shop offers a rotating selection of vintage jackets, blazers, and overcoats, including some one-of-a-kind pieces from the ’20s, ’30s, and ’40s. Prices start at around $75.

    Up next is Tigerlily Vintage in Lakeview, which has been supplying Chicagoans with vintage treasures since 1997. Here you’ll find a mix of classic denim jackets, bomber jackets, and fur-trimmed coats, all with an emphasis on high-quality fabrics and unique details. Prices range from $75 to $200.

    For a more curated experience, check out Shangri-La Vintage where you’ll find hand-picked vintage jackets in excellent condition from the ’50s to the ’80s. Expect to pay a bit more for the luxurious finds, with prices starting at around $150.

    The women-run Kokorokoko Annex in Pilsen offers unique and quirky vintage finds, with a large selection of retro jackets ranging in style from cropped blazers to patchwork denim jackets. Prices start at around $45.

    Last but not least is Crossroads Trading, a second-hand store with locations all over the city, where you can score vintage jackets at incredibly low prices. The selection varies, but you’re sure to find a few gems for under $50.

So there you have it, ten places in Chicago to score the coziest, coolest vintage jackets around. With this guide in hand, you’ll be swathed in retro goodness all winter long –; and looking Chicagogo good while doing it!

Photo by MART PRODUCTION
Photo by Yaritza
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