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Get the Boot: 10 Chicago Stores For Fall Boots

By Jenny Berg
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Photo: via City Soles
By Jenny Berg

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So long, sandals. Flip-flops? It's been real. It's time to tuck away the summer shoes and prep your soles for colder weather. Here's a list of our 10 essential stores for shopping boots in Chicago this season. Where will you be getting your kicks this fall? Let us know in the comments below.

And if you happen to be shop-hopping from city to city, check out our Racked sister sites' guides to cruising boots in Los Angeles, New York, and more.


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1. A Pied

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2037 West Roscoe Street
Chicago, IL 60618
773-281-2210
773-281-2210
Visit Website
We'd hoof it to Roscoe Village anytime to hit up this totally-devoted-to-shoes shop. With fall boot weather setting in, staffers are helping customers pull on styles from brands such as Corso Como and La Canadienne.

2. Belmont Army Surplus

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1318 N Milwaukee Ave
Chicago, IL
(773) 384-8448
(773) 384-8448
Visit Website
If you're looking for a store where staffers are eager to gush over fall trends, this may not be your spot. If you're looking for no-nonsense, fall-leaf-crushing looks for men and women from lines like Palladium and Doc Martens, welcome to Belmont Army Surplus.

3. Lori's Shoes

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824 W Armitage Ave
Chicago, IL 60614
(773) 281-5655
(773) 281-5655
Visit Website
Lori's tagline isn't "the sole of Chicago" for nothing. The beloved spot for women's shoes specializes in styles that are on-trend (yes!) and affordable (yes-er!) This season, the Armitage Avenue shop carries everything from Calvin Klein's slouchy suede "Rae" boots to Carrol's spiffy, black leather booties with pointy toes.

4. City Soles

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2001 W North Ave
Chicago, IL 60647
(773) 489-2001
(773) 489-2001
Visit Website
An established favorite on the local-boutique scene, City Soles is giving Chicago the boot this fall. New selections include tall, brown leather boots with Native-American-inspired details (staffers they can see Mae West in them), and looks from Damen Frost, P. Monjo, and more for men. Want more detail? Hop over to the City Soles website, which has product reviews on video from the store's sole-obsessed owner.

5. AKIRA Bucktown Footwear

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1849 W North Ave
Chicago, IL 60622
(773) 342-8684
(773) 342-8684
Visit Website
You may be from Chicago if... at least half your shoe selection is from Akira Bucktown Footwear. The hometown hero, which has outlets popping up throughout the city like mad, has its roots in footwear. This fall, look for nontraditional boot styles like The Mist Clear Rain Boot in orange, which may be the only rain boots we can see clubbing in.

6. Alcala's Western Wear

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1733 W Chicago Ave
Chicago, IL 60622
(312) 226-0152
(312) 226-0152
Visit Website
This funky shop in Ukrainian Village has Chicago's largest selection of Western boots. There are alligator, roper, and smooth-leather boots for men; lizard, ostrich, and fringed styles for ladies; and even harness baby booties for wee cowboys and girls. If the styles here aren't completely cutting-edge, they are classic and all-American—and perfect for Chicago denizens who are a little bit country (we're raising our hands over here.)

7. Nordstrom

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55 E Grand Ave
Chicago, IL 60611
(312) 464-1515
(312) 464-1515
Visit Website
The clean, airy, and sprawling shoe section at the Michigan Avenue Nordstrom has a friendly and totally efficient sales staff, which can help when you're stepping in and out of a bazillion pairs of boots. And what boots there are. Styles for men, women, and children bear brand names ranging from Tory Burch to Cole Haan and Sperry.

8. Timberland

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Rustic and durable is the name of the game at this Michigan Avenue shop. If you're into hiking, this is a perfect place to plough through practical-but-still-pretty-cute styles, which cater to men, women, and kids. This fall, we're hot on the trail (heh, get it?) of the Women's Earthkeep Trenton Tall Waterproof Boots, which have a side-zipper for easy entry and leather in a lovely tobacco shade.

9. Bloomingdale's

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900 N Michigan Ave
Chicago, IL 60611
(312) 440-4460
(312) 440-4460
Visit Website
Have you stopped by the spankin' new shoe department at the 900 Shops' Bloomies? Ever since the department moved upstairs and expanded, there's a whole new energy. (And this is a good thing.) Fall boot styles come from Luxury Rebel, Isaac Mizrahi, Burberry, Ted Baker, and more.

10. Florodora Shoes

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348 South Dearborn Street
Chicago, IL 60605
312-212-8860
312-212-8860
Visit Website
Steeped in old-timey charm (it's housed in the historic Monadnak building, and feels like a trapped-in-time boudoir), Florodora gets a great selection of tall and ankle boots for fall and winter. The styles are from lines like Colico, which uses Spanish leather, and the small Italian brand Gidigio. Looks, according to a sales rep, are "classic and for everyday, but they have those European details that make them feel a little vintage-inspired, and handmade." Mm, craftsmanship.

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1. A Pied

2037 West Roscoe Street, Chicago, IL 60618
We'd hoof it to Roscoe Village anytime to hit up this totally-devoted-to-shoes shop. With fall boot weather setting in, staffers are helping customers pull on styles from brands such as Corso Como and La Canadienne.
2037 West Roscoe Street
Chicago, IL 60618
773-281-2210
Visit Website

2. Belmont Army Surplus

1318 N Milwaukee Ave, Chicago, IL
If you're looking for a store where staffers are eager to gush over fall trends, this may not be your spot. If you're looking for no-nonsense, fall-leaf-crushing looks for men and women from lines like Palladium and Doc Martens, welcome to Belmont Army Surplus.
1318 N Milwaukee Ave
Chicago, IL
(773) 384-8448
Visit Website

3. Lori's Shoes

824 W Armitage Ave, Chicago, IL 60614
Lori's tagline isn't "the sole of Chicago" for nothing. The beloved spot for women's shoes specializes in styles that are on-trend (yes!) and affordable (yes-er!) This season, the Armitage Avenue shop carries everything from Calvin Klein's slouchy suede "Rae" boots to Carrol's spiffy, black leather booties with pointy toes.
824 W Armitage Ave
Chicago, IL 60614
(773) 281-5655
Visit Website

4. City Soles

2001 W North Ave, Chicago, IL 60647
An established favorite on the local-boutique scene, City Soles is giving Chicago the boot this fall. New selections include tall, brown leather boots with Native-American-inspired details (staffers they can see Mae West in them), and looks from Damen Frost, P. Monjo, and more for men. Want more detail? Hop over to the City Soles website, which has product reviews on video from the store's sole-obsessed owner.
2001 W North Ave
Chicago, IL 60647
(773) 489-2001
Visit Website

5. AKIRA Bucktown Footwear

1849 W North Ave, Chicago, IL 60622
You may be from Chicago if... at least half your shoe selection is from Akira Bucktown Footwear. The hometown hero, which has outlets popping up throughout the city like mad, has its roots in footwear. This fall, look for nontraditional boot styles like The Mist Clear Rain Boot in orange, which may be the only rain boots we can see clubbing in.
1849 W North Ave
Chicago, IL 60622
(773) 342-8684
Visit Website

6. Alcala's Western Wear

1733 W Chicago Ave, Chicago, IL 60622
This funky shop in Ukrainian Village has Chicago's largest selection of Western boots. There are alligator, roper, and smooth-leather boots for men; lizard, ostrich, and fringed styles for ladies; and even harness baby booties for wee cowboys and girls. If the styles here aren't completely cutting-edge, they are classic and all-American—and perfect for Chicago denizens who are a little bit country (we're raising our hands over here.)
1733 W Chicago Ave
Chicago, IL 60622
(312) 226-0152
Visit Website

7. Nordstrom

55 E Grand Ave, Chicago, IL 60611
The clean, airy, and sprawling shoe section at the Michigan Avenue Nordstrom has a friendly and totally efficient sales staff, which can help when you're stepping in and out of a bazillion pairs of boots. And what boots there are. Styles for men, women, and children bear brand names ranging from Tory Burch to Cole Haan and Sperry.
55 E Grand Ave
Chicago, IL 60611
(312) 464-1515
Visit Website

8. Timberland

Chicago, IL 60611
Rustic and durable is the name of the game at this Michigan Avenue shop. If you're into hiking, this is a perfect place to plough through practical-but-still-pretty-cute styles, which cater to men, women, and kids. This fall, we're hot on the trail (heh, get it?) of the Women's Earthkeep Trenton Tall Waterproof Boots, which have a side-zipper for easy entry and leather in a lovely tobacco shade.

9. Bloomingdale's

900 N Michigan Ave, Chicago, IL 60611
Have you stopped by the spankin' new shoe department at the 900 Shops' Bloomies? Ever since the department moved upstairs and expanded, there's a whole new energy. (And this is a good thing.) Fall boot styles come from Luxury Rebel, Isaac Mizrahi, Burberry, Ted Baker, and more.
900 N Michigan Ave
Chicago, IL 60611
(312) 440-4460
Visit Website

10. Florodora Shoes

348 South Dearborn Street, Chicago, IL 60605
Steeped in old-timey charm (it's housed in the historic Monadnak building, and feels like a trapped-in-time boudoir), Florodora gets a great selection of tall and ankle boots for fall and winter. The styles are from lines like Colico, which uses Spanish leather, and the small Italian brand Gidigio. Looks, according to a sales rep, are "classic and for everyday, but they have those European details that make them feel a little vintage-inspired, and handmade." Mm, craftsmanship.
348 South Dearborn Street
Chicago, IL 60605
312-212-8860
Visit Website