What's New
Footwear
Close Footwear
Open Footwear
All Men's Footwear
NEW! Men's Ready To Wear
The Express Lane
Men's Goodyear Welt Shoes
Men's Goodyear Welt Boots
Men's Sneakers
Other Men's Shoes
All Women's Footwear
Women's Dress Shoes
Women's Boots
Women's Sneakers
Women's Slippers
Apparel
Close Apparel
Open Apparel
All Apparel
The Essential Tee
Graphic Tees
Sweatshirts
Hoodies
Hats/Beanies
Accessories
Close Accessories
Open Accessories
All Accessories
Belts
Golf Shoes
Socks
Design Your Own
Info
Close Info
Open Info
Our Story
FAQs
Sizing Guide
Contact
Returns/Exchange
Press
Reviews
Blog/News
My Account
Footwear
Close Footwear
Open Footwear
All Men's Footwear
The Express Lane
Men's Goodyear Welt Shoes
Men's Goodyear Welt Boots
Men's Sneakers
Other Men's Shoes
All Women's Footwear
High Heels
Women's Dress Shoes
Women's Boots
Women's Sneakers
Women's Slippers
Apparel
Close Apparel
Open Apparel
Polo Shirts
The Button Up
The Essential Tee
Graphic Tees
Hoodies
Accessories
Close Accessories
Open Accessories
All Accessories
Back Packs/Briefcases
Travel Bags/Duffles
Belts
Golf Shoes
Socks
Info
Close Info
Open Info
Our Story
FAQs
Sizing Guide
Contact
Returns/Exchange
Press
Reviews
Blog/News
My Account
Search
$
0.00
0
Cart
Home
/ Product Collection /
The Chicago Collection
/ Page 32
The Chicago Collection
Design Your Own
Filters
Style
Select content
Style
Brogue Boots (5)
Brogues (15)
Chelsea Boot (11)
Chukka Boot (5)
Derby (34)
Jodhpur Boot (3)
Lace Up Boots (8)
Monkstraps (22)
Oxford (16)
Saddle Shoe (8)
Slip On (12)
Zip Up Boot (4)
Model
Select content
Model
The Armitage Ave. Derby (10)
The Belmont Ave. Oxford (16)
The Cicero Ave. Single Monk (6)
The Damen Ave. Double Monk (16)
The Dearborn St. Brogue Boot (5)
The Devon Ave. Full Brogue (8)
The Elston Ave. Longwing Blucher (7)
The Fulton St. Chelsea Boot (8)
The Grand Ave. Loafer (12)
The Halstead St. Chelsea Boot (3)
The Kinzie St. Balmoral Boot (1)
The Lincoln Ave. Saddle Shoe (8)
The Madison St. Chukka Boot (5)
The Rush St. Jodhpur Boot (3)
The Sedgwick St. Jumper Boot (2)
The State St. Octavian Buckle Boot (4)
The Wabash Ave. Wholecut Oxford (6)
Finish
Select content
Finish
Burnished (16)
Hand Patina Finish (45)
Signature Finish (75)
Patina Style
Select content
Patina Style
Camo (1)
Marble (14)
Museum (3)
Original (18)
Papiro (10)
Reverse (1)
Color
Select content
Color
Black (14)
Blue (8)
Brown (45)
Burgundy (9)
Cognac (25)
Brown - Dark (28)
Fire (3)
Green (2)
Gray (11)
Khaki (1)
Khaki Green (5)
Brown - Light (1)
Brown - Medium (11)
Navy Blue (13)
Olive Green (1)
Plaid (1)
Purple (2)
Red (2)
Sand (1)
Tartan (2)
Tobacco (1)
Turquoise (2)
Tweed (1)
White (2)
Wine (1)
Materials
Select content
Materials
Blackwatch Wool (1)
Box Calf (8)
Tweed (Small Pattern) (2)
Luxe Suede (Calf) (10)
Croco Embossed Calf Leather (10)
Flannel (3)
Full Grain Leather (4)
Plaid (Grey/Blue) (3)
Herringbone Wool (4)
Houndstooth Wool (1)
Italian Hand Patina Leather (45)
Kid Suede (3)
Luxe Calf (11)
Nailhead Wool (1)
Painted Calf Leather (34)
Patent Leather (2)
Pebble Grain Leather (6)
Plaid Wool (3)
Tartan (2)
Tartan (Blue) (2)
Tweed Wool (3)
Waxed Suede (2)
Accents
Select content
Accents
Bow (2)
Cap Toe (3)
Full Punched (1)
Mask (2)
Metal Bit (2)
Plain Toe (5)
Punched Toe (8)
Tassels (3)
Sole
Select content
Soles
Leather Sole with Rubber Button Injections (120)
Last
The 312
(74)
The 773
(30)
The 847
(3)
The 872
(13)
Filters
Style
Select content
Style
Brogue Boots (5)
Brogues (15)
Chelsea Boot (11)
Chukka Boot (5)
Derby (34)
Jodhpur Boot (3)
Lace Up Boots (8)
Monkstraps (22)
Oxford (16)
Saddle Shoe (8)
Slip On (12)
Zip Up Boot (4)
Model
Select content
Model
The Armitage Ave. Derby (10)
The Belmont Ave. Oxford (16)
The Cicero Ave. Single Monk (6)
The Damen Ave. Double Monk (16)
The Dearborn St. Brogue Boot (5)
The Devon Ave. Full Brogue (8)
The Elston Ave. Longwing Blucher (7)
The Fulton St. Chelsea Boot (8)
The Grand Ave. Loafer (12)
The Halstead St. Chelsea Boot (3)
The Kinzie St. Balmoral Boot (1)
The Lincoln Ave. Saddle Shoe (8)
The Madison St. Chukka Boot (5)
The Rush St. Jodhpur Boot (3)
The Sedgwick St. Jumper Boot (2)
The State St. Octavian Buckle Boot (4)
The Wabash Ave. Wholecut Oxford (6)
Finish
Select content
Finish
Burnished (16)
Hand Patina Finish (45)
Signature Finish (75)
Patina Style
Select content
Patina Style
Camo (1)
Marble (14)
Museum (3)
Original (18)
Papiro (10)
Reverse (1)
Color
Select content
Color
Black (14)
Blue (8)
Brown (45)
Burgundy (9)
Cognac (25)
Brown - Dark (28)
Fire (3)
Green (2)
Gray (11)
Khaki (1)
Khaki Green (5)
Brown - Light (1)
Brown - Medium (11)
Navy Blue (13)
Olive Green (1)
Plaid (1)
Purple (2)
Red (2)
Sand (1)
Tartan (2)
Tobacco (1)
Turquoise (2)
Tweed (1)
White (2)
Wine (1)
Materials
Select content
Materials
Blackwatch Wool (1)
Box Calf (8)
Tweed (Small Pattern) (2)
Luxe Suede (Calf) (10)
Croco Embossed Calf Leather (10)
Flannel (3)
Full Grain Leather (4)
Plaid (Grey/Blue) (3)
Herringbone Wool (4)
Houndstooth Wool (1)
Italian Hand Patina Leather (45)
Kid Suede (3)
Luxe Calf (11)
Nailhead Wool (1)
Painted Calf Leather (34)
Patent Leather (2)
Pebble Grain Leather (6)
Plaid Wool (3)
Tartan (2)
Tartan (Blue) (2)
Tweed Wool (3)
Waxed Suede (2)
Accents
Select content
Accents
Bow (2)
Cap Toe (3)
Full Punched (1)
Mask (2)
Metal Bit (2)
Plain Toe (5)
Punched Toe (8)
Tassels (3)
Sole
Select content
Soles
Leather Sole with Rubber Button Injections (120)
Last
The 312
(74)
The 773
(30)
The 847
(3)
The 872
(13)
Showing 497–512 of 1528 results
Sorted by latest
Sort by popularity
Sort by average rating
Sort by latest
Sort by price: low to high
Sort by price: high to low
The Foster Ave. Monk Sneaker No. 3738
Add to wishlist
$
299.00
Select Size
This product has multiple variants. The options may be chosen on the product page
The Foster Ave. Monk Sneaker No. 5622
Add to wishlist
$
399.00
Select Size
This product has multiple variants. The options may be chosen on the product page
The Ashland Ave. Low Top Sneaker No. 5621
Add to wishlist
$
299.00
Select Size
This product has multiple variants. The options may be chosen on the product page
The Ashland Ave. Low Top Sneaker No. 5614
Add to wishlist
$
299.00
Select Size
This product has multiple variants. The options may be chosen on the product page
The Bosworth Ave. Low Kick Sneaker No. 5610
Add to wishlist
Rated
5.00
out of 5
$
299.00
Select Size
This product has multiple variants. The options may be chosen on the product page
The Damen Ave. Double Monk No. 5609
Add to wishlist
Rated
5.00
out of 5
$
554.00
Select Size
This product has multiple variants. The options may be chosen on the product page
The Ashland Ave. Low Top Sneaker No. 5607
Add to wishlist
$
299.00
Select Size
This product has multiple variants. The options may be chosen on the product page
The Bryn Mawr Ave. Trainer No. 5604
Add to wishlist
$
299.00
Select Size
This product has multiple variants. The options may be chosen on the product page
The State St. Double Buckle Boot No. 5661
Add to wishlist
$
499.00
Select Size
This product has multiple variants. The options may be chosen on the product page
The Bryn Mawr Ave. Trainer No. 2585
Add to wishlist
$
299.00
Select Size
This product has multiple variants. The options may be chosen on the product page
The Bryn Mawr Ave. Trainer No. 2660
Add to wishlist
$
299.00
Select Size
This product has multiple variants. The options may be chosen on the product page
The Sedgwick St. Jump Boot No. 5563
Add to wishlist
$
399.00
Select Size
This product has multiple variants. The options may be chosen on the product page
The Yates Ave. Slip-On Sneaker No. 2804
Add to wishlist
$
299.00
Select Size
This product has multiple variants. The options may be chosen on the product page
The Yates Ave. Slip-On Sneaker No. 2893
Add to wishlist
$
299.00
Select Size
This product has multiple variants. The options may be chosen on the product page
The Bosworth Ave. Low Kick Sneaker No. 5507
Add to wishlist
Rated
5.00
out of 5
$
299.00
Select Size
This product has multiple variants. The options may be chosen on the product page
The Bosworth Ave. Low Kick Sneaker No. 5506
Add to wishlist
Rated
5.00
out of 5
$
299.00
Select Size
This product has multiple variants. The options may be chosen on the product page
1
2
3
…
7
8
Next »
Receive the latest news
Save 15% Off Your First Order!
Sign Up For Our Newsletter
Email Address
subscribe