Where to Find the Best Vintage + Thrift Clothing Shops in Chicago

Vintage Clothing Shop Pilsen Neighborhood Chicago Illinois

I am an avid thrift and vintage clothing shopper, especially after I stopped buying newly produced clothing in 2017 for environmental reasons. Everything that I wear is secondhand, so I know my way around a used clothing store! When I decided to stop buying newly produced clothing, I was worried I would have a hard time finding the full range of clothes I needed. Thankfully, Chicago has an abundant source of secondhand clothing.

Chicago’s vintage clothing scene is surprisingly competitive with lots of people scouring the racks to find hidden gems, but the city’s selection is impeccable.I have compiled a list of my favorite vintage clothing shops and thrift clothing shops in Chicago to help you make your wardrobe a little more sustainable without breaking the bank. There are vintage shops in almost every Chicago neighborhood, but I think the best neighborhoods for secondhand shopping cluster around Wicker Park, Ukrainian Village, and Pilsen. 

Megan in Vintage Clothing Chicago

Best Vintage Clothing Shops in Chicago

Owned by a fellow cat loving lady, Dovetail’s motto is that “You don’t need more stuff. You need better stuff!”. This charming store will equip you with better vintage clothing and home decor items. The owner/curator has a feminine mid-century aesthetic that I love. She finds incredible vintage jewelry that I think is unparalleled in the Chicago market. Many of her pieces are announced on Instagram first, so make sure that you follow her to get a sneak peek. 

This women-of-color owned business is the SH*T. Their branding is spot on, their selection is always amazing, and their brick-and-mortar shop in Ukrainian Village is THE cutest place. It brings me so much joy to walk into their colorful store and find pieces that I fall in love with instantly. Make sure to follow them on social for a preview of all the amazing clothes you can find before even stepping foot into the store! If you can’t visit their storefront, look for their mobile shop inside the colorful orange van named Winnie who frequents street festivals in Chicago.

Lost Girls Vintage Clothing Store Chicago Illinois

This inclusive LGBTQI+ friendly shop has a seriously quirky aesthetic that can be hit or miss, but when it is a hit, it is A HIT. You can find amazing treasures in here, such as a full length faux leopard print coat that is now my party coat or a sparkly one piece swimsuit for your next music festival look. The chatty and friendly owner makes the shopping experience feel personal. 

If you grew up in the 1990s and need of hit of nostalgia every now and then, Kokorokoko is the place for you. Their collection predominantly consists of 80s and 90s sportswear and streetwear. Think swishy tracksuits and graphic Loonytoon tees. Their shop has cheerful murals painted on the walls and a quirky collection of 90s inspired home decor items made by local makers. 

Kokorokoko Vintage Clothing Shop Chicago Illinois

Store B vintage in Wicker Park specializes in early vintage collections for high-end vintage lovers. You’ll find mint condition silk kimonos, perfect 1950s lace cocktail dresses, and even swimwear on the occasion. This place can feel stuffy and unfriendly at times, but the dig can result in some incredible finds. 

This vintage clothing shop has been a strong presence on the Chicago scene for more than a decade, thanks to its amazing collection of affordably priced vintage clothing and accessories, predominantly ranging from 1970s – 1990s. Their helpful and knowledgable staff can typically give you information about where your purchased items were sourced from.

Vintage Clothing Shop Pilsen Neighborhood Chicago Illinois

Part vintage shop, part plant store, I am obsessed with the SHUDIO in Pilsen because their excellently curated collection of on-trend vintage items always has something that I want to wear right now. I have gotten some perfect pieces like pink Levis denim or a velvet overcoat, and my SHUDIO finds always turn into some of my favorite buys. Their friendly staff has always been very cheerful and supportive of my style! 

It is hard to describe this funky vintage store, but you can be sure that it will be packed to the gills with colorful pieces from across the decades. It is well sorted by clothing category, with a large collection of good quality accessories. If you can’t make it to their brick-and-mortar store, they also offer an Etsy shop. 

Vintage Clothing Shop Pilsen Neighborhood Chicago Illinois

Best Thrift Shopping in Chicago

If you follow my MegBethStyle account on Instagram, then you have definitely heard about Crossroads Trading. At any given time, there is a good chance that I am wearing something I bought at one of the four Crossroads Trading locations in Chicago. They are my go-to store for contemporary secondhand clothing. In my opinion, the location in Lakeview is the best of the four because it has lots of space, limited crowds, and a high-intake rate which helps guarantee new pieces all the time. Be careful of bluetag items — they are newly produced items purchased by Crossroads Trading and are often mixed in with used items. 

Megan in Vintage Clothing Chicago

Similar to Crossroads Trading but with a rough-around-the-edges vibe, Buffalo Exchange is my second favorite place for contemporary secondhand clothing in Chicago. Their Wicker Park shop is overwhelmingly crowded with people and merchandise, so the shopping experience can be stressful. But their prices are often better than Crossroads and you can find some unique off-beat items, like an overalls dress or blue suede cape jacket. 

I can never turn down a good thrift shop close to my house, and this one was nearby to my Logan Square apartment. Offering a mixture of furniture, home goods, and lots of contemporary clothes, Monarch Thrift is a reliable source of reasonably priced items. I also love their mission, which funnels proceeds into outreach programming for recently released inmates seeking employment and integration into the community to help reduce recidivism.

Monarch Thirft Shop Logan Square Chicago Illinois

Also in my former neighborhood, the recently opened El Dorado Thrift is located just across the street from the Logan Square Blue Line stop, making for a convenient shopping experience. The spacious shop offers affordable secondhand clothing with inclusive sizing and a good selection of shoes on the back wall. 

With three locations in Chicago, the Brown Elephant is a recognizable chain of thrift shops in Chicago whose proceeds support the Howard Brown Health Center programming for LGBTQI+ communities in the city. The flagship Lakeview location always has a massive assortment of furniture and antiques, but I also think the clothing selection at this location is typically the best. Prices are great!

Photo credits: (1+2) Traverse Blog (3) Lost Girls Vintage (4) Kokorokoko (5-7) Traverse Blog (8) Monarch Thrift (9) Traverse Blog

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