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
The Essential Tee
Graphic Tees
Hoodies
Accessories
Close Accessories
Open Accessories
All Accessories
Back Packs/Briefcases
Travel Bags/Duffles
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 Color /
Gray
/ Page 4
Gray
Design Your Own
Filters
Filters
Showing 49–64 of 200 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 Sedgwick St. Cap Toe Jump Boot No. 5584EX
Add to wishlist
$
399.00
USD
Select Size
This product has multiple variants. The options may be chosen on the product page
The Oak St. Moc Toe Boot No. 5575EX
Add to wishlist
$
499.00
USD
Select Size
This product has multiple variants. The options may be chosen on the product page
The Armitage Ave. Derby No. 5559EX
Add to wishlist
$
339.00
USD
Select Size
This product has multiple variants. The options may be chosen on the product page
The Damen Ave. Double Monk No. 5558EX
Add to wishlist
$
479.00
USD
Select Size
This product has multiple variants. The options may be chosen on the product page
The Madison St. Chukka Boot No. 5534EX
Add to wishlist
$
399.00
USD
Select Size
This product has multiple variants. The options may be chosen on the product page
The State St. Double Buckle Boot No. 5528EX
Add to wishlist
$
499.00
USD
Select Size
This product has multiple variants. The options may be chosen on the product page
The Wabash Ave. Wholecut Oxford No. 5522EX
Add to wishlist
$
349.00
USD
Select Size
This product has multiple variants. The options may be chosen on the product page
The Randolph St. Women’s High Top Sneaker No. 5485
Add to wishlist
$
299.00
USD
Select Size
This product has multiple variants. The options may be chosen on the product page
The Racine Ave. Driving Moccasin No. 5478
Add to wishlist
$
299.00
USD
Select Size
This product has multiple variants. The options may be chosen on the product page
The Bosworth Ave. Low Kick Sneaker No. 5473
Add to wishlist
Rated
5.00
out of 5
$
279.00
USD
Select Size
This product has multiple variants. The options may be chosen on the product page
The Racine Ave. Driving Moccasin No. 5461
Add to wishlist
Rated
5.00
out of 5
$
299.00
USD
Select Size
This product has multiple variants. The options may be chosen on the product page
The Elston Ave. Longwing Blucher No. 5435
Add to wishlist
$
449.00
USD
Select Size
This product has multiple variants. The options may be chosen on the product page
The State St. Double Buckle Boot No. 5431
Add to wishlist
$
359.00
USD
Select Size
This product has multiple variants. The options may be chosen on the product page
The Cicero Ave. Single Monk No. 5424EX
Add to wishlist
$
349.00
USD
Select Size
This product has multiple variants. The options may be chosen on the product page
The Bryn Mawr Ave. Trainer No. 5403
Add to wishlist
$
279.00
USD
Select Size
This product has multiple variants. The options may be chosen on the product page
The Pershing Rd. Monk Strap Loafer No. 5401
Add to wishlist
$
299.00
USD
Select Size
This product has multiple variants. The options may be chosen on the product page
Search
×
All categories
Apparel Collection (150)
Men’s Hosiery (12)
Mid Calf (12)
Outerwear (4)
Hoodies (4)
Shirts (131)
Polo Shirts (3)
Tee Shirts (125)
Graphic Tees (122)
The Cotton Tee (0)
The Eco Blend Tee (0)
The Essential Tee (3)
The Hemp/Cotton Tee (0)
The Button Up (3)
Casual (1)
Dress (2)
Sweatshirts (3)
Graphic Sweatshirts (3)
The Eco Collection (3)
Eco French Terry Zip Hoodie (0)
The Eco Tri-Blend Polo (3)
Collaborations (2)
Custom Products (0)
Custom Products 1167 (0)
Discontinued (0)
DYO (86)
Accessories (13)
Belts (5)
Men’s Boots (12)
Men’s Dress Shoes (10)
Men’s Sneakers (19)
Other Men’s Footwear (10)
Women’s Ballet Flats (1)
Women’s Boots (4)
Women’s Dress Shoes (7)
Women’s Heels (1)
Women’s Slippers (2)
Women’s Sneakers (4)
DYO Golf (9)
Men’s Dress Golf Shoes (9)
DYO-Express (24)
Belts/Accessories (2)
Men’s Boots (7)
Men’s Casual (2)
Men’s Dress Shoes (13)
Gift Cards (1)
Hidden (1)
Luxury Accessories (65)
Belts (26)
The Benton Place Ratchet Belt (1)
The Burton Place Belt (24)
The Delaware Place Belt (1)
Leather Goods (39)
Backpacks/Briefcases (18)
The Logan Square Folio (0)
The Old Town Backpack (10)
The River North Briefcase (8)
The Wicker Park Satchel (0)
The Edgewater Phone Case (0)
The Rogers Park Cigar Case (0)
Travel Bags (22)
The Albany Park Tote (2)
The Bronzeville Duffle Bag (3)
The Bucktown Weekender Bag (3)
The Gold Coast Doctor Bag (5)
The Hyde Park Travel Tote (3)
The Lincoln Park Duffle Bag (2)
The West Loop Gym Bag (1)
The Wrigleyville Tote (3)
Wallets (0)
MTO (1,491)
Men’s Made To Order (1,384)
Men’s Boots (274)
The Dearborn St. Military Brogue Boot (34)
The Elm St. Monk Strap Chukka Boot (3)
The Fulton St. Chelsea Boot (48)
The Halstead St. Chelsea Boot (9)
The Huron St Chelsea Sneaker Boot (7)
The Kinzie St. Balmoral Boot (15)
The Madison St. Chukka Boot (39)
The Oak St. Moc Toe Boot (12)
The Rush St. Jodhpur Boot (37)
The Sedgwick St. Jump Boot (17)
The State St. Double Buckle Boot (39)
The Walton St. Hiking Boot (14)
Men’s Dress Shoes (545)
The Armitage Ave. Derby (49)
The Belden Ave. Split Toe Derby (8)
The Belmont Ave. Oxford (47)
The Cicero Ave. Single Monk (56)
The Damen Ave. Double Monk (101)
The Devon Ave. Full Brogue (48)
The Elston Ave. Longwing Blucher (63)
The Grand Ave. Loafer (91)
The Lincoln Ave. Saddle Shoe (41)
The Wabash Ave. Wholecut Oxford (41)
Men’s Golf Shoes (53)
The Armitage Ave. Derby Golf Shoe (0)
The Belden Ave. Split Toe Golf Shoe (0)
The Belmont Ave. Oxford Golf Shoe (5)
The Cicero Ave. Single Monk Golf Shoe (4)
The Damen Ave. Double Monk Golf Shoe (5)
The Devon Ave. Full Brogue Golf Shoe (5)
The Elston Ave. Longwing Blucher Golf Shoe (8)
The Grand Ave. Loafer Golf Shoe (7)
The Lincoln Ave. Saddle Golf Shoe (16)
The Wabash Ave. Wholecut Oxford Golf Shoe (3)
Men’s High Top Sneakers (46)
Men’s Sneakers (315)
The Adams Ave. Sneaker (2)
The Archer Ave. Corsini Sneaker (0)
The Argyle St. High Top Sneaker (20)
The Ashland Ave. Low Top Sneaker (37)
The Bosworth Ave. Low Kick Sneaker (8)
The Bryn Mawr Ave. Trainer (116)
The California Ave. Sneaker (1)
The Cambridge Ave. Sneaker (1)
The Clark St. High Kick Sneaker (10)
The Division St. High Top (5)
The Foster Ave. Monk Sneaker (29)
The Huron St. Chelsea Sneaker (7)
The Ogden Ave. Sneaker (1)
The Ridge Ave. Sneaker (38)
The Touhy Ave. Belgian Sneaker (22)
The Wells St. High Top Sneaker (4)
The Yates Ave. Slip-On Sneaker (15)
Other Men’s Shoes (201)
The Cermak Rd. Wellington Loafer (48)
The Franklin St. Chukka Boot (2)
The Hubbard St. Chukka Boot (1)
The North Ave. Boat Shoe (0)
The Pershing Rd. Monk Strap Loafer (26)
The Pulaski Rd. Drake Slipper (12)
The Racine Ave. Driving Shoe (42)
The Sheffield Ave. Moccasin (9)
The Sheridan Rd. Belgian Loafer (55)
The Stoney Island Ave. Yacht Loafer (6)
MTO Shirts (0)
Women’s Made to Order (107)
Women’s Boots (34)
The Astor St. Lace Up Brogue (4)
The Canal St. Lace-up Captoe Boot (11)
The Lake St. Military Brogue Boot (8)
The LaSalle St. Chelsea Boot (11)
Women’s Couture Collection (0)
Couture Flats (0)
The Chester Ave. Ballet Flat (0)
The Fairfield Ave Ballet Flat (0)
The Francisco Ave Ballet Flat (0)
Couture Heels (0)
The Adams St. Boot (0)
The Artesian Ave. High Heel (0)
The Austin Ave. High Heel (0)
The Baker Ave. High Heel (0)
The Baldwin Ave. High Heel (0)
The Bell Ave. High Heel (0)
The Beverly Ave. High Heel (0)
The Bowen Ave. High Heel (0)
The Carmen Ave. High Heel (0)
Women’s Dress Shoes (41)
The Clybourn Ave. Derby Wingtip (6)
The Diversey Ave. Saddle Shoe (1)
The Fullerton Ave. Kiltie Monkstrap (10)
The Kedzie Ave. Loafer (6)
The Latrobe Ave. Oxford (3)
The Montrose Ave. Full Brogue (9)
The Rosemont Ave. Double Monk (6)
Women’s Slippers (12)
The Hinsdale Rd. Slipper (3)
The Mannheim Rd. Slipper (9)
Women’s Tennis Shoes and Sneakers (20)
The Burnham Ave. Trainer (11)
The Caldwell Ave. Slip-On Sneaker (3)
The Lawrence Ave. Tennis Shoe (4)
The Randolph St. High Top Sneaker (2)
Out of Stock (3)
RTW (18)
Ready To Wear Footwear (18)
Men’s Dress Shoes (18)
Armitage Ave. Derby RTW (1)
Belden Ave. Split Toe Derby RTW (1)
Belmont Ave. Oxford RTW (3)
Damen Ave. Double Monk RTW (2)
Devon Ave. Full Brogue RTW (1)
Elston Ave. Longwing Blucher (0)
Grand Ave. Loafer RTW (4)
Wabash Ave. Wholecut Oxford RTW (6)
Shoe Care (8)
Insoles (1)
Shoe Laces (3)
Shoe Polish (1)
Shoe Trees (3)
Special Edition (0)
The 8000 Series (215)
The Express Lane (254)
The Armitage Ave. Derby – Express (14)
The Belden Ave. Split Toe Derby – Express (7)
The Belmont Ave. Oxford Express (23)
The Bosworth Ave. Sneaker Express (6)
The Bryn Mawr Ave Trainer Express (22)
The Cicero Ave. Single Monk Express (14)
The Damen Ave. Double Monk Express (21)
The Dearborn St. Military Brogue Express (8)
The Devon Ave. Full Brogue Express (13)
The Elston Ave. Longwing Blucher Express (11)
The Fulton St. Chelsea Boot Express (17)
The Grand Ave. Loafer Express (20)
The Kinzie St. Balmoral Boot Express (4)
The Lincoln Ave. Saddle Shoe Express (4)
The Madison St. Chukka Boot Express (11)
The Oak St. Moc Toe Boot Express (4)
The Rush St. Jodphur Boot Express (6)
The Sedgwick St. Cap Toe Boot Express (6)
The State St. Buckle Boot Express (1)
The Wabash Ave. Wholecut Express (38)
The Walton St. Hiking Boot Express (4)
Uncategorized (0)
Whiskers Laces (0)
Athletic Sneaker Laces (0)
Boot Laces (0)
Dress Laces (0)
Golf Laces (0)
Sneaker Laces (0)
