Log In
/
Logout
My Account
Help
Shopping Bag
Search
Search
Daily Deals & Offers
Sign Up
View More Departments
Shoes
Clothing
Bags & Handbags
Watches
Sunglasses
Accessories
Jewelry
Electronics
Housewares
Beauty
Gift Guide
Women
Men
Kids
Shoes
Clothing
Bags
Accessories
Gift Guide
Women's
Men's
Kids'
Brands
shoes
>
Mens
>
Shoes
>
Boots
>
Ankle
>
D
465
items found
Narrow Your Choices
Style
Chukka
(51)
Athletic
(21)
Demi Boot
(18)
Bootie
(11)
Pac Boot
(10)
Moccasin
(5)
Size
3.5
5
6
6.5
7
7.5
8
8.5
9
9.5
10
10.5
11
11.5
12
12.5
13
13.5
14
15
16
17
OS
Color
Brown
(179)
Black
(162)
Tan
(29)
Gray
(18)
Multi
(13)
Beige
(8)
Green
(8)
Blue
(6)
Taupe
(6)
White
(6)
Khaki
(5)
Olive
(5)
Red
(5)
Mahogany
(3)
Metallic
(3)
Burgundy
(2)
Neutral
(2)
Yellow
(2)
Bronze
(1)
Gold
(1)
Silver
(1)
Brand
310 Motoring
(1)
A. Testoni
(1)
Acorn
(2)
Alexander Hotto
(3)
Allen-Edmonds
(1)
Ariat
(2)
Asolo
(8)
Baffin
(3)
Banana Blues
(4)
Bass
(1)
Bearpaw
(2)
Bedstu
(4)
Ben Sherman
(3)
Bikkembergs
(1)
Blokes
(3)
Boreal
(2)
BRUNO MAGLI
(3)
Calvin Klein
(6)
Camper
(3)
Carhartt
(4)
Carolina
(3)
Caterpillar
(6)
Chippewa
(6)
Clarks
(1)
Cole Haan
(11)
Columbia
(9)
Converse
(1)
Costume National
(4)
Creative Recreation
(1)
Deer Stags
(3)
Dickies
(4)
Diesel
(6)
Dockers
(1)
Donald J Pliner
(26)
Dr. Martens
(20)
DSQUARED2
(4)
Earth
(2)
ECCO
(2)
Ecko Unltd
(3)
Fitzwell
(12)
Fratelli Rossetti
(7)
GBX
(3)
Giorgio Brutini
(2)
Givenchy
(1)
Golden Retriever
(1)
GoLite
(5)
Gravis
(1)
Harley-Davidson
(10)
Harrys of London
(5)
Hi-Tec
(4)
Hunter
(3)
Ipath
(1)
Irish Setter
(4)
Jeffrey Fitzhugh
(3)
John Fluevog
(2)
John Varvatos
(3)
Johnston & Murphy
(2)
JUMP
(1)
Kamik
(3)
Kayland
(2)
Keen
(4)
Kenneth Cole New York
(1)
Kenneth Cole Reaction
(10)
La Sportiva
(5)
Lacoste
(2)
Laredo
(1)
Lassen
(8)
Lowa
(5)
Lugz
(10)
Mad Rock
(1)
Magnum
(1)
Mark Nason
(9)
Montrail
(1)
New Balance Classics
(3)
Nunn Bush
(1)
Oakley
(8)
Old Gringo
(2)
ONETrueSaxon
(2)
Pikolinos
(1)
PUMA
(3)
Raichle
(1)
Ralph Lauren Collection
(3)
Red Wing Shoes
(4)
Robert Wayne
(7)
Rockport
(1)
Roper
(1)
Ryan Rowe
(1)
Salomon
(3)
Scarpa
(2)
Schmoove
(1)
Sebago
(1)
SKECHERS
(5)
SKECHERS Work
(1)
Sorel
(10)
Sperry Top-Sider
(3)
Stacy Adams
(1)
Steve Madden
(13)
Swear
(1)
Taryn Rose
(2)
Ted Baker
(4)
Teva
(2)
The North Face
(11)
Timberland
(22)
To Boot New York
(2)
Tommy Hilfiger
(2)
Triple Five Soul
(1)
Tsubo
(4)
Type Z
(6)
UGG
(1)
Vans
(2)
Vasque
(4)
Via Spiga
(1)
Wolverine
(12)
WORX by Red Wing Shoes
(7)
Heel Height
Flat (0in - 5/8in)
Low (5/8in - 1 1/4in)
Medium (1 3/8in - 2 1/2in)
Sort By:
Newest
Most Popular
Name
Lowest Price
Highest Price
% Off
1
2
3
4
...
5
Next
Ryan Rowe
Campbell
$52.90
(
81% off
MSRP $275.00)
Donald J Pliner
Moritz
$86.14
(
80% off
MSRP $428.00)
Donald J Pliner
Blane
$70.04
(
80% off
MSRP $348.00)
Donald J Pliner
Blane
$70.04
(
80% off
MSRP $348.00)
Donald J Pliner
Moritz
$93.40
(
78% off
MSRP $428.00)
Alexander Hotto
31022
$101.60
(
69% off
MSRP $332.00)
Alexander Hotto
31052
$100.80
(
69% off
MSRP $320.00)
Alexander Hotto
31045
$105.60
(
69% off
MSRP $336.00)
John Varvatos
Shearling Scuttlebutt
$175.20
(
65% off
MSRP $498.00)
John Varvatos
Warren Chucka Boot
$167.20
(
65% off
MSRP $475.00)
Tsubo
Warra
$50.75
(
64% off
MSRP $140.00)
Bedstu
Deputy
$60.00
(
64% off
MSRP $165.00)
John Fluevog
Shawn
$54.00
(
64% off
MSRP $148.50)
Bedstu
Blown
$80.00
(
64% off
MSRP $220.00)
Bedstu
Blown
$80.00
(
64% off
MSRP $220.00)
Jeffrey Fitzhugh
One Twenty
$48.00
(
64% off
MSRP $135.00)
Jeffrey Fitzhugh
El Cap
$56.00
(
64% off
MSRP $155.00)
Jeffrey Fitzhugh
El Cap
$56.00
(
64% off
MSRP $155.00)
John Fluevog
Murdoch
$115.60
(
64% off
MSRP $318.00)
Harrys of London
Bentley
$196.00
(
64% off
MSRP $550.00)
Harrys of London
Bentley
$196.00
(
64% off
MSRP $550.00)
Lassen
Bancroft
$46.00
(
63% off
MSRP $125.00)
Allen-Edmonds
Hayden
$92.50
(
61% off
MSRP $236.00)
Sebago
Whetstone
$60.00
(
60% off
MSRP $150.00)
310 Motoring
Durare
$48.00
(
60% off
MSRP $120.00)
Givenchy
G2164
$201.26
(
59% off
MSRP $495.00)
Via Spiga
Gerald
$55.00
(
58% off
MSRP $130.00)
Ralph Lauren Collection
Cannelton
$292.00
(
58% off
MSRP $695.00)
Ralph Lauren Collection
Erwin
$179.00
(
58% off
MSRP $425.00)
Ralph Lauren Collection
Rangoon
$189.00
(
58% off
MSRP $450.00)
ONETrueSaxon
Bowline
$78.26
(
57% off
MSRP $180.00)
ONETrueSaxon
Bowline
$78.26
(
57% off
MSRP $180.00)
The North Face
Bozeman Boot
$70.85
(
56% off
MSRP $160.00)
Kayland
Super Ice
$192.00
(
56% off
MSRP $439.95)
Swear
Jack 6
$116.00
(
56% off
MSRP $266.00)
Fitzwell
Vicente
$59.00
(
56% off
MSRP $135.00)
Donald J Pliner
Pedro
$185.00
(
56% off
MSRP $420.00)
Ted Baker
Risotto
$255.00
(
56% off
MSRP $575.00)
Mad Rock
Mountain
$79.16
(
55% off
MSRP $175.95)
To Boot New York
Verona
$158.00
(
55% off
MSRP $348.00)
To Boot New York
Shaw
$159.00
(
55% off
MSRP $350.00)
Blokes
Natty Bloke
$180.00
(
55% off
MSRP $398.00)
Kenneth Cole Reaction
Take A Dare
$65.00
(
55% off
MSRP $145.00)
Mark Nason
Blackmore
$225.00
(
55% off
MSRP $495.00)
Harrys of London
Bentley
$260.00
(
55% off
MSRP $575.00)
Harrys of London
Ed
$260.00
(
55% off
MSRP $575.00)
Harrys of London
Ed
$260.00
(
55% off
MSRP $575.00)
Ted Baker
Panna
$310.00
(
55% off
MSRP $695.00)
DSQUARED2
AB320194
$481.00
(
55% off
MSRP $1,074.00)
Blokes
Alpine Bloke
$163.00
(
54% off
MSRP $358.00)
Dr. Martens
Marceaux Patrick-Chelsea Boot
$50.60
(
54% off
MSRP $110.00)
Dr. Martens
Monkey Peter-7 Eye With White Sole
$57.50
(
54% off
MSRP $125.00)
BRUNO MAGLI
Rullo
$290.00
(
53% off
MSRP $615.00)
Vans
Chukka Fleece
$52.25
(
53% off
MSRP $110.00)
Vans
Chukka Fleece
$52.25
(
53% off
MSRP $110.00)
Ariat
Dillon
$75.00
(
53% off
MSRP $159.95)
Ariat
Dillon
$75.00
(
53% off
MSRP $159.95)
Kenneth Cole New York
N-charge
$92.00
(
53% off
MSRP $195.00)
Timberland
2.0
$52.25
(
53% off
MSRP $110.00)
Robert Wayne
Disturb
$60.72
(
53% off
MSRP $130.00)
Ted Baker
Catla
$355.00
(
53% off
MSRP $750.00)
Carolina
Domestic 6" Plain Toe ST
$91.42
(
52% off
MSRP $188.50)
Carolina
Domestic 8" Broad Toe Metatarsal Guard
$95.06
(
52% off
MSRP $196.00)
Creative Recreation
Montana
$80.00
(
52% off
MSRP $166.00)
Kayland
M11
$187.20
(
51% off
MSRP $379.95)
Carolina
Domestic 6" Broad Toe Metatarsal Guard
$89.73
(
51% off
MSRP $185.00)
Fitzwell
Reuben
$56.81
(
51% off
MSRP $115.00)
Fitzwell
Reuben
$56.81
(
51% off
MSRP $115.00)
The North Face
Arctic Pull On
$50.06
(
50% off
MSRP $100.00)
UGG
Eilers
$80.00
(
50% off
MSRP $160.00)
Teva
Tamur Mid
$47.50
(
50% off
MSRP $95.00)
Teva
Kendal
$40.00
(
50% off
MSRP $80.00)
Roper
Hiker/Chukka Design
$60.00
(
50% off
MSRP $120.00)
Golden Retriever
Scout Waterproof Leather ST 6"
$76.00
(
50% off
MSRP $152.00)
Ecko Unltd
Kolb
$35.00
(
50% off
MSRP $70.00)
Ecko Unltd
Vanquish
$33.50
(
50% off
MSRP $67.00)
Wolverine
Telstar Chukka Steel-Toe
$55.00
(
50% off
MSRP $110.00)
Schmoove
Charlie Mountain-Split Nubuck
$120.75
(
50% off
MSRP $242.00)
Calvin Klein
Layton
$92.00
(
49% off
MSRP $180.00)
Bearpaw
Alta
$58.65
(
49% off
MSRP $115.00)
Bearpaw
Alta
$58.65
(
49% off
MSRP $115.00)
Taryn Rose
Enrico
$200.10
(
49% off
MSRP $395.00)
Taryn Rose
Enrico
$200.10
(
49% off
MSRP $395.00)
Bedstu
Bunker Hill
$103.50
(
48% off
MSRP $198.00)
Kenneth Cole Reaction
U Know Who
$70.15
(
48% off
MSRP $135.00)
Blokes
Killer Bloke
$182.85
(
48% off
MSRP $350.00)
PUMA
Puma Explorer
$43.99
(
48% off
MSRP $85.00)
PUMA
Puma Explorer
$43.99
(
48% off
MSRP $85.00)
Donald J Pliner
Jiro
$238.05
(
48% off
MSRP $460.00)
Ecko Unltd
Vale
$51.75
(
48% off
MSRP $100.00)
Dr. Martens
9728
$58.19
(
47% off
MSRP $110.00)
Sorel
Cheyanne®
$45.46
(
47% off
MSRP $85.00)
Sorel
Cold Mountain
$45.46
(
47% off
MSRP $85.00)
Sorel
Cold Mountain® Zip
$45.46
(
47% off
MSRP $85.00)
Sorel
Hood River®
$58.82
(
47% off
MSRP $110.00)
Sorel
Hood River®
$58.82
(
47% off
MSRP $110.00)
Lugz
Port
$41.80
(
47% off
MSRP $79.00)
Timberland
Earthkeepers® Leather and Fabric Chukka
$57.90
(
47% off
MSRP $110.00)
Dr. Martens
Ronnie 8 Eye Boot
$69.00
(
47% off
MSRP $130.00)
Dr. Martens
Charles 7 Tie Lace To Toe Chukka
$69.00
(
47% off
MSRP $130.00)
Sort By:
Newest
Most Popular
Name
Lowest Price
Highest Price
% Off
1
2
3
4
...
5
Next