Thrifting for Style Staples in Chicago

Thrifting for Style Staples in Chicago

Logan Square | Wicker Park | Lincoln Park

During our trip to Chicago for the ALL IN Wrestling event, I actually stayed in the city with friends and left Adam to his wrestling weekend. To kill some time before my friend Kristina (Stina) got off from work, I wandered around with her hubby Tom in their neighborhood of Logan Square. After grabbing a coffee I inquired about thrifting or vintage outlets in the area. This guy is probably a seasoned professional when it comes to shopping. His wifey Stina used to be a manager for Urban Outfitters for YEARS and I happened to be staying in their spare bedroom aka Stina’s closet space. Seriously, this girl needs to host a garage sale or something! I mentioned that I’m constantly on the hunt for the perfect vintage Levi’s/Wrangler denim jacket or denim jeans that I can turn into cutoffs. Tom lead the way to the train and we headed to the Wicker Park neighborhood to a place where I could die and go to heaven…


This chain retailer based in the midwest sells a plethora of basics, vintage resale, Hawaiian shirts, 90s/80s prints, cheap sunglasses of all shapes and sizes, FANNY PACKS and so much more.

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Photo: @ragstock

I walked in my jaw dropped. Inside Ragstock were graphic tees, menswear, denim cutoffs and skirts. A giant wall of jewel toned sunglasses drew me in like a moth to light. There’s this giant wall of sunglasses for like $7.00 a piece and they had every shape and size, color, lens filter and frame. Around the corner was a wall of FANNY PACKS… and then I bumped into this round rack stuffed with VINTAGE DENIM jackets. Fucking score. Poor Tom, my shopping buddy was stuck carrying all my shit, like the gentleman he is. Ragstock had two floors. I reminded me of Red Light Vintage in Seattle. The upstairs is dedicated to new stock and vintage items for men and women from leather jackets to 80s motif prints. Downstairs is dedicated to a lot of sale items, tights, accessories, Hawaiian shirts and Halloween stuff.

Crossroads Trading Co.

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Photo: Timeout Chicago

This buy/sell/trade staple is scattered all over the United States in most major cities and nearby college towns. The collegiate market is perfect for this thrift chain. They buy seasonally and on-trend items from all different brands from fast fashion to designer labels. I used to frequent the one in my own college town near the University of Washington in Seattle. My closet would fluctuate so much from walking around campus in all four seasons to working at H&M all throughout college, I would take and sell stuff at Crossroads just to make an extra buck, or I would trade it in for some new life for my style.

Urban Outfitters Clark Street aka The Surplus Store

So, I have a love/hate relationship with Urban Outfitters. My Internet husband and I have both worked for the company and have both left the company and the retail industry in general. My friend Kristina, who hosted me in Chicago worked for them for nearly 5+ years and even she can’t stay away. Sometimes they can make some damn good prints and I simply love them for graphic T-shirts, business casual blouses, and their shoe selection. Pick and choose your battles, people.

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They USED to make great denim, but lately their BDG skinny jeans are not the greatest quality. If you shopped there in 2008 up to present day, you know what I’m talking about. On the other hand, their “Mom jeans” and “destroyed” jeans are really great quality denim if you want that loose, boyfriend fit.


Photo: Back when I worked for Urban Outfitters I was dubbed the “denim specialist” and put together make shift look books with selfie mirror pictures. Cringing! 

Anyway, I digress… so, we ended up at the Clark Street Urban Outfitters, the surplus store of Chicago. Which means, it’s not merchandised like the boutique atmosphere that all stores have, but instead it is just racks on racks of tops, pants, denim, outerwear, menswear, lingerie, swimwear and “dime out” pieces, which are like super sale items that are discontinued. So, what that all means is that it’s basically all sale items. On top of that, it being Labor Day weekend, there was an extra 40% off sale… on top of sale markdowns. Need I say more?

There are many many neighborhoods that I didn’t venture out to, since our trip was so short, but Logan Square and a few train stops away in Wicker Park and Lincoln Park there are a lot more treasures that need a home in your style rotation. If you find yourself in Chicago: check out a few of these neighborhoods and their thrift & resale shops.



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