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Floradora Shoes

The best shoe stores in Chicago

The best shoe stores in Chicago have all the brands and styles you love, from high-end to comfy and functional

By Jess Keys and Laura Rote

The best shoe stores in Chicago offer the best kind of shop until you drop experience. After all, shoes can take an outfit from boring to fabulous, help you make a great impression on a romantic date, and they never make you feel fat. Whether you need new shoes to go with a great new ensemble you got from one of Chicago's best clothing stores or something special to wear out to dinner at a new fine dining restaurant, these shops are a great place to start. 


The best shoe stores in Chicago

Photograph: Courtesy Click

1. Click Shoes

Shopping Shoes Wrigleyville

You know that big rush of happiness that comes along with scoring a great pair of shoes at a great price? You'll experience a lot of that at this staple shoe store on Southport. It's often referred to as a "hidden gem" for good reason. The shop is known for its stylish shoes, accessories and apparel—brands like Vince Camuto and Sam Edelman, Sundry, Michael Lauren and more—often at hefty discounts.

John Fluevog Shoes
Photograph: Crystal Garcia

2. John Fluevog Shoes

Shopping Shoes Wicker Park

For high-end, standout styles that add the element of funk you were looking for to any outfit, look no further than John Fluevog. Besides being in a cool space in Wicker Park, you can also bank on good customer service. If you're looking for a new pair of kicks that will turn heads, this is your store.

Dursen Shoes
Photograph: Courtesy Dursen Shoes

3. Dursen Shoes

Shopping Shoes Wicker Park

Dapper dudes know this Chicago shoe shop is the spot to score quality and stylish dress shoes, oxfords, boots and loafers at prices that won't break their budgets. (Seriously—they start at $85). Stop by to browse the selection of American-designed, genuine Italian leather footwear, or feel free to stay awhile and play some pool. 

4. Florodora Shoes

Shopping Shoes Loop

Housed in the same historic Monadnock Building as the original Florodora boutique, this sibling features some of the most unique women’s shoes in the city. The selection includes funky, smaller brands like Coclico, Ann Roth and Mea Shadow. In addition to kicks, the shop also stocks accessories like handbags and jewelry. The storefront was actually occupied by a shoe store called Hassel’s about 100 years ago, so we like to think that the space is going back to its roots.

Photograph: Max Herman

5. A Pied

Shopping Shoes North Center

The charming A Pied isn't huge, but we always find something we love at this Roscoe Village women's shoe boutique: flats, booties, pumps, heels, sandals, you name it. Even better: The shoes are cute, comfortable and always unique. While you may not have heard of all the brands here, these shoes will definitely get you some attention.

6. BucketFeet

Shopping Shoes Loop

Chicago-based shoe retailers BucketFeet are just one of the many stores to take up residence in Block 37. This shop stocks a wide selection of the brand's signature shoes, each decorated with an artist's custom design. New designs are added frequently, so check back often to find the latest footwear masterpieces. You'll also find a location in Bucktown.


7. Lori's Designer Shoes and Accessories

Shopping Shoes Lincoln Park

In a collective quest for the latest in designer shoes, stylish women cautiously navigate this 4,500-square-foot Lincoln Park boutique's thigh-high stacks of shoeboxes. The shop's large selection (curated by Lori herself) includes major brands like Dolce Vita and Jeffrey Campbell and makes battling the weekend crowds worth it. Lori's also stocks a small selection of handbags, jewelry and apparel.

8. Tom's Shoes

Shopping Shoes Wicker Park

Shop for those ubiquitous slip-ons and contribute to a great cause, all while getting your caffeine fix. One of the few Tom's locations to boast a "One for One" coffee shop, this Wicker Park spot is a great place to kill a few birds with one stone. Have a latte while browsing men's and women's shoes, eyewear, apparel and accessories.

Akira Shoes
Photograph: Marzena Abrahamik

9. Akira–Downtown Footwear

Shopping Boutiques Loop

Akira is a Chicago fashionista’s dream—the perfect combination of youthful trends and affordability. The footwear stores are even more enthralling than the awesome men’s and women’s clothing stores, as new, innovative designers cover tables with spiked boots and platforms. You can also often find student-friendly sales and tons of new stock.


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