Order before 1PM PST on 12/23 with FREE SHIPPING for GUARANTEED DELIVERY BEFORE XMAS!Order before 1PM PST on 12/23 with FREE SHIPPING for GUARANTEED DELIVERY BEFORE XMAS!Order before 1PM PST on 12/23 with FREE SHIPPING for GUARANTEED DELIVERY BEFORE XMAS!Order before 1PM PST on 12/23 with FREE SHIPPING for GUARANTEED DELIVERY BEFORE XMAS!

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shoes > Remove Remove productTypeFacet Shoes > Remove Remove categoryFacet Boots > Remove Remove subCategoryFacet Ankle > Remove Remove gender Mens > Remove Remove attrFacet_Style Chukka
162 items found

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Frye - Dakota Mid Lace Thumbnail
New!
Frye
Dakota Mid Lace
 $182.00
Clarks - Un.colonial Thumbnail
New!
Clarks
Un.colonial
 $145.00
Clarks - Wallabee - Mens Thumbnail
New!
Clarks
Wallabee - Mens
 $150.00
Clarks - Wallabee - Mens Thumbnail
New!
Clarks
Wallabee - Mens
 $150.00
Cole Haan - Air Dryden Chukka Thumbnail
New!
Cole Haan
Air Dryden Chukka
 $227.95

Donald J Pliner - Upton Thumbnail
New!
Donald J Pliner
Upton
 $265.00
Donald J Pliner - Upton Thumbnail
New!
Donald J Pliner
Upton
 $265.00
John Varvatos - Ginsburg Chukka Thumbnail
New!
John Varvatos
Ginsburg Chukka
 $202.00
John Varvatos - Fillmore Chukka Thumbnail
New!
John Varvatos
Fillmore Chukka
 $369.00
John Varvatos - Ginsburg Chukka Thumbnail
New!
John Varvatos
Ginsburg Chukka
 $202.00

John Varvatos - Fillmore Chukka Thumbnail
New!
John Varvatos
Fillmore Chukka
 $369.00
Clarks - Wallabee - Mens Thumbnail
Clarks
Wallabee - Mens
 $115.00
Clarks - Wallabee Boot- Mens Thumbnail
Clarks
Wallabee Boot- Mens
 $120.00
Skechers - Mariner Thumbnail
Skechers
Mariner
 $69.00
Dunham - Pelham Thumbnail
Dunham
Pelham
 $129.00
SALE!
$109.63

Dickies - WD6930 Thumbnail
Dickies
WD6930
 $89.00
SALE!
$80.10
ECCO - Berlin GTX Boot Thumbnail
ECCO
Berlin GTX Boot
 $200.00
Sperry Top-Sider - Barracuda Chukka Boot Thumbnail
Sperry Top-Sider
Barracuda Chukka Boot
 $99.90
SALE!
$82.00
Clarks - Roar Thumbnail
Clarks
Roar
 $110.00
Clarks - Roar Thumbnail
Clarks
Roar
 $110.00

The North Face - Men's Hayden Chukka Thumbnail
The North Face
Men's Hayden Chukka
 $99.95
Frye - Owen Crepe Chukka Thumbnail
Frye
Owen Crepe Chukka
 $202.00
Frye - Owen Crepe Chukka Thumbnail
Frye
Owen Crepe Chukka
 $202.00
UGG - Worley Thumbnail
UGG
Worley
 $154.00
Clarks - Roar Thumbnail
Clarks
Roar
 $110.00
SALE!
$88.00

Columbia - Mckenzie River® Chukka Thumbnail
Columbia
Mckenzie River® Chukka
 $100.00
Columbia - Mckenzie River® Chukka Thumbnail
Columbia
Mckenzie River® Chukka
 $94.95
Clarks - Wallabee Boot Thumbnail
Clarks
Wallabee Boot
 $130.00
Dr. Martens - Aiken Thumbnail
Dr. Martens
Aiken
 $119.95
Dr. Martens - Robson Griffin-4 Eye Plain Toe Chukka Thumbnail
Dr. Martens
Robson Griffin-4 Eye Plain Toe Chukka
 $99.95

Dr. Martens - Robson Griffin-4 Eye Plain Toe Chukka Thumbnail
Dr. Martens
Robson Griffin-4 Eye Plain Toe Chukka
 $99.95
Dr. Martens - Monkey Peter-7 Eye With White Sole Thumbnail
Dr. Martens
Monkey Peter-7 Eye With White Sole
 $124.95
SALE!
$106.01
Dr. Martens - Monkey Peter-7 Eye Boot Thumbnail
Dr. Martens
Monkey Peter-7 Eye Boot
 $109.95
SALE!
$89.06
Oakley - Sabot Mid Thumbnail
Oakley
Sabot Mid
 $100.00
Oakley - Sabot High Thumbnail
Oakley
Sabot High
 $114.00

Oakley - Sabot Mid Thumbnail
Oakley
Sabot Mid
 $100.00
Oakley - Sabot High Thumbnail
Oakley
Sabot High
 $114.00
Frye - Manny Chukka Thumbnail
Frye
Manny Chukka
 $252.00
Frye - Manny Chukka Thumbnail
Frye
Manny Chukka
 $252.00
Timberland - Earthkeepers® Leather and Fabric Chukka Thumbnail
Timberland
Earthkeepers® Leather and Fabric Chukka
 $109.95
SALE!
$85.35

Timberland - Earthkeepers® Leather and Fabric Chukka Thumbnail
Timberland
Earthkeepers® Leather and Fabric Chukka
 $109.95
SALE!
$87.96
Timberland Urban - Rugged Street Chukka Thumbnail
Timberland Urban
Rugged Street Chukka
 $84.95
SALE!
$76.28
Timberland Urban - Rugged Street Chukka Thumbnail
Timberland Urban
Rugged Street Chukka
 $84.95
Timberland Urban - F3 Chukka Thumbnail
Timberland Urban
F3 Chukka
 $94.95
SALE!
$80.12
Timberland Urban - F3 Chukka Thumbnail
Timberland Urban
F3 Chukka
 $94.95
SALE!
$85.46

Dr. Martens - Charles 7 Tie Lace To Toe Chukka Thumbnail
Dr. Martens
Charles 7 Tie Lace To Toe Chukka
 $129.95
SALE!
$104.50
Dr. Martens - Charles 7 Tie Lace To Toe Chukka Thumbnail
Dr. Martens
Charles 7 Tie Lace To Toe Chukka
 $129.95
Dr. Martens - Charles 7 Tie Lace To Toe Chukka Thumbnail
Dr. Martens
Charles 7 Tie Lace To Toe Chukka
 $129.95
SALE!
$92.94
Fila - Bull Strap Thumbnail
Fila
Bull Strap
 $69.95
Red Wing Shoes - Heritage Work Chukka Thumbnail
Red Wing Shoes
Heritage Work Chukka
 $229.95

Red Wing Shoes - Heritage Work Chukka Thumbnail
Red Wing Shoes
Heritage Work Chukka
 $229.95
Lassen - Richie Thumbnail
Lassen
Richie
 $89.00
SALE!
$80.10
Lassen - Joe Thumbnail
Lassen
Joe
 $89.00
SALE!
$80.10
Lassen - Richie Thumbnail
Lassen
Richie
 $89.00
SALE!
$76.03
Lassen - Joe Thumbnail
Lassen
Joe
 $89.00
SALE!
$72.75

Columbia - Terratrek® Mid Omni-Tech® Thumbnail
Columbia
Terratrek® Mid Omni-Tech®
 $114.95
Columbia - Terratrek® Mid Omni-Tech® Thumbnail
Columbia
Terratrek® Mid Omni-Tech®
 $114.95
Columbia - Vizza® Chukka Thumbnail
Columbia
Vizza® Chukka
 $109.95
Columbia - Vizza® Chukka Thumbnail
Columbia
Vizza® Chukka
 $109.95
Dr. Martens - Whitfield 3-Eye Boot Thumbnail
Dr. Martens
Whitfield 3-Eye Boot
 $119.95

Dr. Martens - Graham Thumbnail
Dr. Martens
Graham
 $89.95
Dr. Martens - Whitfield 3-Eye Boot Thumbnail
Dr. Martens
Whitfield 3-Eye Boot
 $119.95
Dr. Martens - Aiken Thumbnail
Dr. Martens
Aiken
 $119.95
Dr. Martens - Graham Thumbnail
Dr. Martens
Graham
 $89.95
Frye - Manny Chukka Thumbnail
Frye
Manny Chukka
 $252.00

Fossil - Jacobson Boot Thumbnail
Fossil
Jacobson Boot
 $144.00
Fossil - Jacobson Boot Thumbnail
Fossil
Jacobson Boot
 $144.00
Columbia - Mckenzie River® Chukka Thumbnail
Columbia
Mckenzie River® Chukka
 $100.00
Clarks - Cobra Thumbnail
Clarks
Cobra
 $110.00
SALE!
$88.00
Clarks - Cobra Thumbnail
Clarks
Cobra
 $110.00

Clarks - Cobra Nylon Thumbnail
Clarks
Cobra Nylon
 $90.00
SALE!
$81.00
Clarks - Cobra Nylon Thumbnail
Clarks
Cobra Nylon
 $90.00
SALE!
$78.00
Clarks - Adder Thumbnail
Clarks
Adder
 $100.00
Clarks - Adder Thumbnail
Clarks
Adder
 $100.00
Clarks - Adder Thumbnail
Clarks
Adder
 $100.00

Clarks - Desert Lynx Thumbnail
Clarks
Desert Lynx
 $110.00
Clarks - Desert Lynx Thumbnail
Clarks
Desert Lynx
 $110.00
SALE!
$96.80
Clarks - Ecosteps Wallabee Thumbnail
Clarks
Ecosteps Wallabee
 $140.00
SALE!
$112.00
Clarks - Ecosteps Wallabee Thumbnail
Clarks
Ecosteps Wallabee
 $140.00
Clarks - Un.dylan Thumbnail
Clarks
Un.dylan
 $145.00

Clarks - Un.dylan Thumbnail
Clarks
Un.dylan
 $145.00
Johnston & Murphy - Runnell Chukka Boot Thumbnail
Johnston & Murphy
Runnell Chukka Boot
 $134.00
Johnston & Murphy - Runnell Chukka Boot Thumbnail
Johnston & Murphy
Runnell Chukka Boot
 $134.00
Ahnu - Fillmore Thumbnail
Ahnu
Fillmore
 $113.95
Dunham - Windsor Mid Cut Thumbnail
Dunham
Windsor Mid Cut
 $116.00

Dunham - Windsor Mid Cut Thumbnail
Dunham
Windsor Mid Cut
 $116.00
Hush Puppies - Drivetrain Thumbnail
Hush Puppies
Drivetrain
 $127.95
Hush Puppies - Drivetrain Thumbnail
Hush Puppies
Drivetrain
 $127.95
Skechers - Trended Thumbnail
Skechers
Trended
 $75.90
Skechers - Trended Thumbnail
Skechers
Trended
 $75.90
SALE!
$67.50

Skechers - Trended Thumbnail
Skechers
Trended
 $75.90
SALE!
$67.50
Rockport - Trudell Thumbnail
Rockport
Trudell
 $129.95
Rockport - Brosnihan Thumbnail
Rockport
Brosnihan
 $109.95
Wolverine - Omni MX® Waterproof Lace-Up Chukka Thumbnail
Wolverine
Omni MX® Waterproof Lace-Up Chukka
 $134.00
Rockport - Brosnihan Thumbnail
Rockport
Brosnihan
 $109.95

Earth - Vanish Thumbnail
Earth
Vanish
 $133.00
Earth - Vanish Thumbnail
Earth
Vanish
 $133.00
Allen-Edmonds - Calhoun Thumbnail
Allen-Edmonds
Calhoun
 $219.00
Allen-Edmonds - Calhoun Thumbnail
Allen-Edmonds
Calhoun
 $219.00
Allen-Edmonds - Calhoun Thumbnail
Allen-Edmonds
Calhoun
 $219.00