GOING FAST
EXTRA 20% OFF*
Save on select styles with code EXTRA20
Shop Now
*Exclusions apply

Skip to search results Skip to filters Skip to sort Skip to selected filters

Size 10 Medium Size Chukka Boots

86 items found

Filters

Search Results

Nunn Bush - Circuit DC Plain Toe Chukka. Color Black. On sale for $54.97. MSRP $90.00. 39% off. 3.8 out of 5 stars

Black Nunn Bush Circuit DC Plain Toe Chukka

Black Nunn Bush Circuit DC Plain Toe Chukka

+3

Brand Name: Nunn Bush
Product Name: Circuit DC Plain Toe Chukka
Gender: Men's
Color: Black
Price: $54.97MSRP: $9039% OFF
Rating: 4Rated 4 stars out of 5(54)

Rockport - Classic Break Chukka. Color Dark Brown Leather. $159.95. 4.3 out of 5 stars

Brown Rockport Classic Break Chukka

Brown Rockport Classic Break Chukka

Brand Name: Rockport
Product Name: Classic Break Chukka
Gender: Men's
Color: Dark Brown Leather
Price: $159.95
Rating: 4Rated 4 stars out of 5(215)

Florsheim - Norwalk Plain Toe Chukka Boot. Color Black Crazy Horse. $150.00. 4.6 out of 5 stars

Black Florsheim Norwalk Plain Toe Chukka Boot

Black Florsheim Norwalk Plain Toe Chukka Boot

Brand Name: Florsheim
Product Name: Norwalk Plain Toe Chukka Boot
Gender: Men's
Color: Black Crazy Horse
Price: $150
Rating: 5Rated 5 stars out of 5(76)

Nunn Bush - Ozark 2.0 Plain Toe Chukka Leather Boots. Color Black. On sale for $89.95. MSRP $120.00. 25% off. 4.3 out of 5 stars

Black Nunn Bush Ozark 2.0 Plain Toe Chukka Leather Boots

Black Nunn Bush Ozark 2.0 Plain Toe Chukka Leather Boots

+3

Brand Name: Nunn Bush
Product Name: Ozark 2.0 Plain Toe Chukka Leather Boots
Gender: Men's
Color: Black
Price: $89.95MSRP: $12025% OFF
Rating: 4Rated 4 stars out of 5(13)

Twisted X - MDM0033. Color Bomber/Tan. $149.95. 5.0 out of 5 stars

Brown Twisted X MDM0033

Brown Twisted X MDM0033

Brand Name: Twisted X
Product Name: MDM0033
Gender: Men's
Color: Bomber/Tan
Price: $149.95
Rating: 5Rated 5 stars out of 5(7)

Florsheim - Lodge Plain Toe 3-eye Chukka Boots. Color Brown Crazy Horse. $140.00. 4.0 out of 5 stars

Brown Florsheim Lodge Plain Toe 3-eye Chukka Boots

Brown Florsheim Lodge Plain Toe 3-eye Chukka Boots

+2

Brand Name: Florsheim
Product Name: Lodge Plain Toe 3-eye Chukka Boots
Gender: Men's
Color: Brown Crazy Horse
Price: $140
Rating: 4Rated 4 stars out of 5(5)

Nunn Bush - Denali Plain Toe Chukka. Color Black. On sale for $89.95. MSRP $120.00. 25% off. 4.4 out of 5 stars

Black Nunn Bush Denali Plain Toe Chukka

Black Nunn Bush Denali Plain Toe Chukka

+2

Brand Name: Nunn Bush
Product Name: Denali Plain Toe Chukka
Gender: Men's
Color: Black
Price: $89.95MSRP: $12025% OFF
Rating: 4Rated 4 stars out of 5(107)

Nunn Bush - Odell 2.0 Wingtip Dress Casual Chukka Leather Boots. Color Tan. On sale for $89.95. MSRP $120.00. 25% off. 4.5 out of 5 stars

Tan Nunn Bush Odell 2.0 Wingtip Dress Casual Chukka Leather Boots

Tan Nunn Bush Odell 2.0 Wingtip Dress Casual Chukka Leather Boots

+1

Brand Name: Nunn Bush
Product Name: Odell 2.0 Wingtip Dress Casual Chukka Leather Boots
Gender: Men's
Color: Tan
Price: $89.95MSRP: $12025% OFF
Rating: 4Rated 4 stars out of 5(15)

Born - Harrison. Color Brown Full Grain. $145.00. 4.3 out of 5 stars

Brown Born Harrison

Brown Born Harrison

+2

Brand Name: Born
Product Name: Harrison
Gender: Men's
Color: Brown Full Grain
Price: $145
Rating: 4Rated 4 stars out of 5(115)

Nunn Bush - Karnak Moc Toe Boots Lightweight Comfortable Chukka. Color Black. On sale for $89.95. MSRP $120.00. 25% off. 4.3 out of 5 stars

Black Nunn Bush Karnak Moc Toe Boots Lightweight Comfortable Chukka

Black Nunn Bush Karnak Moc Toe Boots Lightweight Comfortable Chukka

+1

Brand Name: Nunn Bush
Product Name: Karnak Moc Toe Boots Lightweight Comfortable Chukka
Gender: Men's
Color: Black
Price: $89.95MSRP: $12025% OFF
Rating: 4Rated 4 stars out of 5(13)

Johnston & Murphy - Calder Chukka. Color Black Tumbled Full Grain. $178.95. 4.0 out of 5 stars

Black Johnston & Murphy Calder Chukka

Black Johnston & Murphy Calder Chukka

+4

Brand Name: Johnston & Murphy
Product Name: Calder Chukka
Gender: Men's
Color: Black Tumbled Full Grain
Price: $178.95
Rating: 4Rated 4 stars out of 5(3)

Florsheim - Forge Plain Toe Chukka. Color Cognac. $130.00. 4.0 out of 5 stars

Tan Florsheim Forge Plain Toe Chukka

Tan Florsheim Forge Plain Toe Chukka

+3

Brand Name: Florsheim
Product Name: Forge Plain Toe Chukka
Gender: Men's
Color: Cognac
Price: $130
Rating: 4Rated 4 stars out of 5(25)

Johnston & Murphy - Xc+ Parker Chukka. Color Black Waterproof Full Grain. $188.95.

Black Johnston & Murphy Xc+ Parker Chukka

Black Johnston & Murphy Xc+ Parker Chukka

+2

Brand Name: Johnston & Murphy
Product Name: Xc+ Parker Chukka
Gender: Men's
Color: Black Waterproof Full Grain
Price: $188.95
Rating

OluKai - Papaku ‘Ili Chukka Boots. Color Graphite/Graphite. $159.99. 5.0 out of 5 stars

Black OluKai Papaku ‘Ili Chukka Boots

Black OluKai Papaku ‘Ili Chukka Boots

Brand Name: OluKai
Product Name: Papaku ‘Ili Chukka Boots
Gender: Men's
Color: Graphite/Graphite
Price: $159.99
Rating: 5Rated 5 stars out of 5(2)

Florsheim - Lodge Plain Toe Chukka Boots. Color Black Crazy Horse. $145.00. 4.5 out of 5 stars

Black Florsheim Lodge Plain Toe Chukka Boots

Black Florsheim Lodge Plain Toe Chukka Boots

+3

Brand Name: Florsheim
Product Name: Lodge Plain Toe Chukka Boots
Gender: Men's
Color: Black Crazy Horse
Price: $145
Rating: 4Rated 4 stars out of 5(144)

Florsheim - Rucci Plain Toe Chukka Boot. Color Brown Smooth. $154.94. 4.3 out of 5 stars

Brown Florsheim Rucci Plain Toe Chukka Boot

Brown Florsheim Rucci Plain Toe Chukka Boot

Brand Name: Florsheim
Product Name: Rucci Plain Toe Chukka Boot
Gender: Men's
Color: Brown Smooth
Price: $154.94
Rating: 4Rated 4 stars out of 5(53)

Dansko - Tony. Color Tan. $194.95.

Tan Dansko Tony

Tan Dansko Tony

+2

Brand Name: Dansko
Product Name: Tony
Gender: Men's
Color: Tan
Price: $194.95
Rating

Kenneth Cole - Wilhem. Color Mocha. On sale for $99.00. MSRP $164.95. 40% off.

Brown Kenneth Cole Wilhem

Brown Kenneth Cole Wilhem

+2

Brand Name: Kenneth Cole
Product Name: Wilhem
Gender: Men's
Color: Mocha
Price: $99MSRP: $164.9540% OFF
Rating

Clarks - Shacre Boots. Color Beeswax Leather. On sale for $81.21. MSRP $120.00. 32% off. 4.2 out of 5 stars

Brown Clarks Shacre Boots

Brown Clarks Shacre Boots

+4

Brand Name: Clarks
Product Name: Shacre Boots
Gender: Men's
Color: Beeswax Leather
Price: $81.21MSRP: $12032% OFF
Rating: 4Rated 4 stars out of 5(70)

Clarks - Steadwell Mid. Color Black Leather. On sale for $99.00. MSRP $110.00. 10% off.

Black Clarks Steadwell Mid

Black Clarks Steadwell Mid

Brand Name: Clarks
Product Name: Steadwell Mid
Gender: Men's
Color: Black Leather
Price: $99MSRP: $11010% OFF
Rating

Johnston & Murphy - Upton Chukka Boots. Color Tan Full Grain. On sale for $151.60. MSRP $169.00. 10% off. 4.7 out of 5 stars

Tan Johnston & Murphy Upton Chukka Boots

Tan Johnston & Murphy Upton Chukka Boots

Brand Name: Johnston & Murphy
Product Name: Upton Chukka Boots
Gender: Men's
Color: Tan Full Grain
Price: $151.60MSRP: $16910% OFF
Rating: 5Rated 5 stars out of 5(173)

Red Wing Heritage - Work Chukka. Color Briar Oil Slick. $289.99. 4.5 out of 5 stars

Mahogany Red Wing Heritage Work Chukka

Mahogany Red Wing Heritage Work Chukka

Brand Name: Red Wing Heritage
Product Name: Work Chukka
Gender: Men's
Color: Briar Oil Slick
Price: $289.99
Rating: 4Rated 4 stars out of 5(87)

Born - Brock. Color Taupe Distressed Leather. $150.00. 4.5 out of 5 stars

Taupe Born Brock

Taupe Born Brock

Brand Name: Born
Product Name: Brock
Gender: Men's
Color: Taupe Distressed Leather
Price: $150
Rating: 5Rated 5 stars out of 5(20)

Ariat - Spitfire H2O. Color Reliable Brown. $139.95. 4.3 out of 5 stars

Brown Ariat Spitfire H2O

Brown Ariat Spitfire H2O

Brand Name: Ariat
Product Name: Spitfire H2O
Gender: Men's
Color: Reliable Brown
Price: $139.95
Rating: 4Rated 4 stars out of 5(57)

Sperry - Mini Lug Chukka. Color Other Brown. On sale for $105.00. MSRP $150.00. 30% off.

Brown Sperry Mini Lug Chukka

Brown Sperry Mini Lug Chukka

+2

Brand Name: Sperry
Product Name: Mini Lug Chukka
Gender: Men's
Color: Other Brown
Price: $105MSRP: $15030% OFF
Rating

Martin Dingman - Bad Weather Boot. Color Walnut. Low Stock. On sale for $237.00. MSRP $395.00. 40% off.

Low Stock

Brown Martin Dingman Bad Weather Boot

Brown Martin Dingman Bad Weather Boot

+2

Brand Name: Martin Dingman
Product Name: Bad Weather Boot
Gender: Men's
Color: Walnut
Price: $237MSRP: $39540% OFF
Rating

SOREL - Slabtown 62' Stoic Mid. Color Black/Bleached Ceramic. $160.00.

Black SOREL Slabtown 62' Stoic Mid

Black SOREL Slabtown 62' Stoic Mid

+2

Brand Name: SOREL
Product Name: Slabtown 62' Stoic Mid
Gender: Men's
Color: Black/Bleached Ceramic
Price: $160
Rating

ECCO - Metropole Milan Chukka Boots. Color Black. Low Stock. On sale for $175.45. MSRP $194.95. 10% off. 4.0 out of 5 stars

Low Stock

Black ECCO Metropole Milan Chukka Boots

Black ECCO Metropole Milan Chukka Boots

+2

Brand Name: ECCO
Product Name: Metropole Milan Chukka Boots
Gender: Men's
Color: Black
Price: $175.45MSRP: $194.9510% OFF
Rating: 4Rated 4 stars out of 5(1)

Ariat - Spitfire. Color American Flag Print. $129.95. 4.5 out of 5 stars

Multi Ariat Spitfire

Multi Ariat Spitfire

+6

Brand Name: Ariat
Product Name: Spitfire
Gender: Men's
Color: American Flag Print
Price: $129.95
Rating: 5Rated 5 stars out of 5(428)

Sperry - Newton Boots. Color Taupe. On sale for $148.50. MSRP $165.00. 10% off. 5.0 out of 5 stars

Taupe Sperry Newton Boots

Taupe Sperry Newton Boots

Brand Name: Sperry
Product Name: Newton Boots
Gender: Men's
Color: Taupe
Price: $148.50MSRP: $16510% OFF
Rating: 5Rated 5 stars out of 5(1)

Kenneth Cole - Winston. Color Mocha Multi. On sale for $114.98. MSRP $159.95. 28% off.

Brown Kenneth Cole Winston

Brown Kenneth Cole Winston

+2

Brand Name: Kenneth Cole
Product Name: Winston
Gender: Men's
Color: Mocha Multi
Price: $114.98MSRP: $159.9528% OFF
Rating

Steve Madden - Harros. Color Black. Low Stock. On sale for $70.00. MSRP $100.00. 30% off.

Low Stock

Black Steve Madden Harros

Black Steve Madden Harros

+2

Brand Name: Steve Madden
Product Name: Harros
Gender: Men's
Color: Black
Price: $70MSRP: $10030% OFF
Rating

ECCO - London Lace Up Waterproof Chukka Boots. Color Black Nubuck. Low Stock. On sale for $206.95. MSRP $229.95. 10% off. 4.0 out of 5 stars

Low Stock

Black ECCO London Lace Up Waterproof Chukka Boots

Black ECCO London Lace Up Waterproof Chukka Boots

Brand Name: ECCO
Product Name: London Lace Up Waterproof Chukka Boots
Gender: Men's
Color: Black Nubuck
Price: $206.95MSRP: $229.9510% OFF
Rating: 4Rated 4 stars out of 5(2)

Twisted X - MXC0001. Color Brown. $159.95. 4.4 out of 5 stars

Brown Twisted X MXC0001

Brown Twisted X MXC0001

Brand Name: Twisted X
Product Name: MXC0001
Gender: Men's
Color: Brown
Price: $159.95
Rating: 4Rated 4 stars out of 5(7)

Florsheim - Launch Plain Toe Chukka Boots. Color Cognac Multi. On sale for $121.50. MSRP $135.00. 10% off.

Tan Florsheim Launch Plain Toe Chukka Boots

Tan Florsheim Launch Plain Toe Chukka Boots

Brand Name: Florsheim
Product Name: Launch Plain Toe Chukka Boots
Gender: Men's
Color: Cognac Multi
Price: $121.50MSRP: $13510% OFF
Rating

ALDO - Kenora. Color Brown. On sale for $85.00. MSRP $130.00. 35% off. 4.7 out of 5 stars

Brown ALDO Kenora

Brown ALDO Kenora

Brand Name: ALDO
Product Name: Kenora
Gender: Men's
Color: Brown
Price: $85MSRP: $13035% OFF
Rating: 5Rated 5 stars out of 5(3)

Barbour - Barbour Readhead. Color Cognac. $220.00.

Tan Barbour Barbour Readhead

Tan Barbour Barbour Readhead

+2

Brand Name: Barbour
Product Name: Barbour Readhead
Gender: Men's
Color: Cognac
Price: $220
Rating

Born - Erik. Color Brown (Castano). On sale for $120.00. MSRP $160.00. 25% off.

Brown Born Erik

Brown Born Erik

Brand Name: Born
Product Name: Erik
Gender: Men's
Color: Brown (Castano)
Price: $120MSRP: $16025% OFF
Rating

Twisted X - MDM0003. Color Bomber. $139.95. 4.6 out of 5 stars

Bone Twisted X MDM0003

Bone Twisted X MDM0003

Brand Name: Twisted X
Product Name: MDM0003
Gender: Men's
Color: Bomber
Price: $139.95
Rating: 5Rated 5 stars out of 5(25)

Kenneth Cole - Vesto. Color Medium Brown. On sale for $77.47. MSRP $118.95. 35% off.

Brown Kenneth Cole Vesto

Brown Kenneth Cole Vesto

+2

Brand Name: Kenneth Cole
Product Name: Vesto
Gender: Men's
Color: Medium Brown
Price: $77.47MSRP: $118.9535% OFF
Rating

Barbour - Blaine Chukka Boots. Color Choc Suede. Low Stock. $245.00. 5.0 out of 5 stars

Low Stock

Brown Barbour Blaine Chukka Boots

Brown Barbour Blaine Chukka Boots

+2

Brand Name: Barbour
Product Name: Blaine Chukka Boots
Gender: Men's
Color: Choc Suede
Price: $245
Rating: 5Rated 5 stars out of 5(1)

Vance - Blackwell. Color Black. On sale for $62.99. MSRP $89.99. 30% off.

Black Vance Blackwell

Black Vance Blackwell

+2

Brand Name: Vance
Product Name: Blackwell
Gender: Men's
Color: Black
Price: $62.99MSRP: $89.9930% OFF
Rating

Clarks - Wallabee Boots. Color Beeswax. $149.95. 4.5 out of 5 stars

Brown Clarks Wallabee Boots

Brown Clarks Wallabee Boots

+4

Brand Name: Clarks
Product Name: Wallabee Boots
Gender: Men's
Color: Beeswax
Price: $149.95
Rating: 4Rated 4 stars out of 5(62)

Born - Ethan. Color Taupe (Avola). On sale for $97.48. MSRP $150.00. 35% off. 2.0 out of 5 stars

Taupe Born Ethan

Taupe Born Ethan

Brand Name: Born
Product Name: Ethan
Gender: Men's
Color: Taupe (Avola)
Price: $97.48MSRP: $15035% OFF
Rating: 2Rated 2 stars out of 5(1)

Steve Madden - Daviston. Color Brown. On sale for $115.50. MSRP $165.00. 30% off.

Brown Steve Madden Daviston

Brown Steve Madden Daviston

+2

Brand Name: Steve Madden
Product Name: Daviston
Gender: Men's
Color: Brown
Price: $115.50MSRP: $16530% OFF
Rating

. Carhartt - Plain Toe Wedge Chukka. Color Dark Brown. $139.99. 3.6 out of 5 stars

Brown Carhartt Plain Toe Wedge Chukka

Brown Carhartt Plain Toe Wedge Chukka

Brand Name: Carhartt
Product Name: Plain Toe Wedge Chukka
Gender: Men's
Color: Dark Brown
Price: $139.99
Rating: 4Rated 4 stars out of 5(5)

Frye - Astor Chukka. Color Tan. Low Stock. On sale for $107.34. MSRP $178.00. 40% off. 4.0 out of 5 stars

Low Stock

Tan Frye Astor Chukka

Tan Frye Astor Chukka

Brand Name: Frye
Product Name: Astor Chukka
Gender: Men's
Color: Tan
Price: $107.34MSRP: $17840% OFF
Rating: 4Rated 4 stars out of 5(23)

Steve Madden - Tabriz. Color Brown. On sale for $98.00. MSRP $140.00. 30% off. 2.0 out of 5 stars

Brown Steve Madden Tabriz

Brown Steve Madden Tabriz

Brand Name: Steve Madden
Product Name: Tabriz
Gender: Men's
Color: Brown
Price: $98MSRP: $14030% OFF
Rating: 2Rated 2 stars out of 5(1)

Twisted X - MDM0014. Color Copper. $139.95. 4.8 out of 5 stars

Bronze Twisted X MDM0014

Bronze Twisted X MDM0014

Brand Name: Twisted X
Product Name: MDM0014
Gender: Men's
Color: Copper
Price: $139.95
Rating: 5Rated 5 stars out of 5(6)

Florsheim - Rucci Plain Toe Chukka. Color Cognac. $155.00. 4.8 out of 5 stars

Tan Florsheim Rucci Plain Toe Chukka

Tan Florsheim Rucci Plain Toe Chukka

Brand Name: Florsheim
Product Name: Rucci Plain Toe Chukka
Gender: Men's
Color: Cognac
Price: $155
Rating: 5Rated 5 stars out of 5(19)

Oboz - Burke Chukka. Color Grizzly. Low Stock. $140.00. 4.1 out of 5 stars

Low Stock

Brown Oboz Burke Chukka

Brown Oboz Burke Chukka

Brand Name: Oboz
Product Name: Burke Chukka
Gender: Men's
Color: Grizzly
Price: $140
Rating: 4Rated 4 stars out of 5(17)

Twisted X - MDM0057. Color Oiled Saddle/Midnight. $149.95. 5.0 out of 5 stars

Brown Twisted X MDM0057

Brown Twisted X MDM0057

Brand Name: Twisted X
Product Name: MDM0057
Gender: Men's
Color: Oiled Saddle/Midnight
Price: $149.95
Rating: 5Rated 5 stars out of 5(4)

Allen Edmonds - Chandler. Color Pecan. $525.00. 4.4 out of 5 stars

Brown Allen Edmonds Chandler

Brown Allen Edmonds Chandler

+2

Brand Name: Allen Edmonds
Product Name: Chandler
Gender: Men's
Color: Pecan
Price: $525
Rating: 4Rated 4 stars out of 5(64)

Allen Edmonds - Parkversboot. Color Navy. Low Stock. On sale for $385.00. MSRP $550.00. 30% off. 5.0 out of 5 stars

Low Stock

Navy Allen Edmonds Parkversboot

Navy Allen Edmonds Parkversboot

+2

Brand Name: Allen Edmonds
Product Name: Parkversboot
Gender: Men's
Color: Navy
Price: $385MSRP: $55030% OFF
Rating: 5Rated 5 stars out of 5(1)

Allen Edmonds - Chandler Chukka. Color Antique Hickory. $525.00.

Black Allen Edmonds Chandler Chukka

Black Allen Edmonds Chandler Chukka

Brand Name: Allen Edmonds
Product Name: Chandler Chukka
Gender: Men's
Color: Antique Hickory
Price: $525
Rating

Twisted X - MDM0019. Color Bomber/Neon Orange. $139.95. 4.9 out of 5 stars

Brown Twisted X MDM0019

Brown Twisted X MDM0019

Brand Name: Twisted X
Product Name: MDM0019
Gender: Men's
Color: Bomber/Neon Orange
Price: $139.95
Rating: 5Rated 5 stars out of 5(8)

Twisted X - MDM0049. Color Bomber. $139.95. 4.0 out of 5 stars

Bone Twisted X MDM0049

Bone Twisted X MDM0049

Brand Name: Twisted X
Product Name: MDM0049
Gender: Men's
Color: Bomber
Price: $139.95
Rating: 4Rated 4 stars out of 5(4)

Twisted X - MDM0080. Color Rubberized Brown. $139.95. 2.0 out of 5 stars

Brown Twisted X MDM0080

Brown Twisted X MDM0080

Brand Name: Twisted X
Product Name: MDM0080
Gender: Men's
Color: Rubberized Brown
Price: $139.95
Rating: 2Rated 2 stars out of 5(1)

Ariat - Recon Country. Color Distressed Brown. $149.95. 4.2 out of 5 stars

Brown Ariat Recon Country

Brown Ariat Recon Country

Brand Name: Ariat
Product Name: Recon Country
Gender: Men's
Color: Distressed Brown
Price: $149.95
Rating: 4Rated 4 stars out of 5(61)

To Boot New York - Monaco. Color Slate. $425.00.

Gray To Boot New York Monaco

Gray To Boot New York Monaco

+2

Brand Name: To Boot New York
Product Name: Monaco
Gender: Men's
Color: Slate
Price: $425
Rating

Sperry - Coldbay Chukka Realtree MM. Color Olive. On sale for $114.05. MSRP $120.00. 5% off.

Olive Sperry Coldbay Chukka Realtree MM

Olive Sperry Coldbay Chukka Realtree MM

Brand Name: Sperry
Product Name: Coldbay Chukka Realtree MM
Gender: Men's
Color: Olive
Price: $114.05MSRP: $1205% OFF
Rating

Red Wing Heritage - Weekend Chukka. Color Copper Rough & Tough 1. $269.99. 4.3 out of 5 stars

Brown Red Wing Heritage Weekend Chukka

Brown Red Wing Heritage Weekend Chukka

+3

Brand Name: Red Wing Heritage
Product Name: Weekend Chukka
Gender: Men's
Color: Copper Rough & Tough 1
Price: $269.99
Rating: 4Rated 4 stars out of 5(50)

Steve Madden - Hestonn. Color Chocolate. On sale for $76.99. MSRP $109.99. 30% off. 3.7 out of 5 stars

Brown Steve Madden Hestonn

Brown Steve Madden Hestonn

+6

Brand Name: Steve Madden
Product Name: Hestonn
Gender: Men's
Color: Chocolate
Price: $76.99MSRP: $109.9930% OFF
Rating: 4Rated 4 stars out of 5(80)

Cole Haan - Berkshire Chelsea Boots. Color Black/Truffle. Low Stock. On sale for $134.18. MSRP $250.00. 46% off. 4.5 out of 5 stars

Low Stock

Brown Cole Haan Berkshire Chelsea Boots

Brown Cole Haan Berkshire Chelsea Boots

+2

Brand Name: Cole Haan
Product Name: Berkshire Chelsea Boots
Gender: Men's
Color: Black/Truffle
Price: $134.18MSRP: $25046% OFF
Rating: 5Rated 5 stars out of 5(26)

Florsheim - Anthem Plain Toe Chukka Boots. Color Black. $145.00. 4.4 out of 5 stars

Black Florsheim Anthem Plain Toe Chukka Boots

Black Florsheim Anthem Plain Toe Chukka Boots

+4

Brand Name: Florsheim
Product Name: Anthem Plain Toe Chukka Boots
Gender: Men's
Color: Black
Price: $145
Rating: 4Rated 4 stars out of 5(12)

Clarks - Wallaston Boot. Color Dark Sand Suede. On sale for $91.00. MSRP $120.00. 24% off. 4.0 out of 5 stars

Brown Clarks Wallaston Boot

Brown Clarks Wallaston Boot

+5

Brand Name: Clarks
Product Name: Wallaston Boot
Gender: Men's
Color: Dark Sand Suede
Price: $91MSRP: $12024% OFF
Rating: 4Rated 4 stars out of 5(5)

Tommy Hilfiger - Bage. Color Cognac Tumble. On sale for $59.50. MSRP $119.00. 50% off. 4.5 out of 5 stars

Tan Tommy Hilfiger Bage

Tan Tommy Hilfiger Bage

+4

Brand Name: Tommy Hilfiger
Product Name: Bage
Gender: Men's
Color: Cognac Tumble
Price: $59.50MSRP: $11950% OFF
Rating: 5Rated 5 stars out of 5(2)

UGG - Neumel Weather Hybrid. Color Chestnut/Whitecap. $189.95. 4.3 out of 5 stars

Brown UGG Neumel Weather Hybrid

Brown UGG Neumel Weather Hybrid

+3

Brand Name: UGG
Product Name: Neumel Weather Hybrid
Gender: Men's
Color: Chestnut/Whitecap
Price: $189.95
Rating: 4Rated 4 stars out of 5(137)

OluKai - Papaku 'Ili. Color Black/Black. $159.99. 4.0 out of 5 stars

Black OluKai Papaku 'Ili

Black OluKai Papaku 'Ili

+3

Brand Name: OluKai
Product Name: Papaku 'Ili
Gender: Men's
Color: Black/Black
Price: $159.99
Rating: 4Rated 4 stars out of 5(181)

Dockers - Esmond. Color Taupe. On sale for $66.26. MSRP $95.00. 30% off. 3.5 out of 5 stars

Taupe Dockers Esmond

Taupe Dockers Esmond

+5

Brand Name: Dockers
Product Name: Esmond
Gender: Men's
Color: Taupe
Price: $66.26MSRP: $9530% OFF
Rating: 4Rated 4 stars out of 5(2)

. UGG - Neumel. Color Black Suede. $149.95. 4.8 out of 5 stars

Black UGG Neumel

Black UGG Neumel

+2

Brand Name: UGG
Product Name: Neumel
Gender: Men's
Color: Black Suede
Price: $149.95
Rating: 5Rated 5 stars out of 5(6170)

Clarks - Desert Trek. Color Black Suede 3. $140.00. 4.5 out of 5 stars

Black Clarks Desert Trek

Black Clarks Desert Trek

+4

Brand Name: Clarks
Product Name: Desert Trek
Gender: Men's
Color: Black Suede 3
Price: $140
Rating: 4Rated 4 stars out of 5(109)

Clarks - Shepton. Color Dark Brown Leather. On sale for $77.00. MSRP $110.00. 30% off. 1.6 out of 5 stars

Brown Clarks Shepton

Brown Clarks Shepton

+6

Brand Name: Clarks
Product Name: Shepton
Gender: Men's
Color: Dark Brown Leather
Price: $77MSRP: $11030% OFF
Rating: 2Rated 2 stars out of 5(7)

Eastland 1955 Edition - Jack. Color Peanut. Low Stock. On sale for $119.99. MSRP $125.00. 4% off. 4.4 out of 5 stars

Low Stock

Brown Eastland 1955 Edition Jack

Brown Eastland 1955 Edition Jack

+1

Brand Name: Eastland 1955 Edition
Product Name: Jack
Gender: Men's
Color: Peanut
Price: $119.99MSRP: $1254% OFF
Rating: 4Rated 4 stars out of 5(10)

Hey Dude - Bradley Chukka. Color Brown/Black. On sale for $83.38. MSRP $84.99. 2% off. 5.0 out of 5 stars

Brown Hey Dude Bradley Chukka

Brown Hey Dude Bradley Chukka

+3

Brand Name: Hey Dude
Product Name: Bradley Chukka
Gender: Men's
Color: Brown/Black
Price: $83.38MSRP: $84.992% OFF
Rating: 5Rated 5 stars out of 5(1)

Nunn Bush - Chase Plain Toe Chukka Contemporary Fashion Boot. Color Black. On sale for $64.95. MSRP $95.00. 32% off. 3.9 out of 5 stars

Black Nunn Bush Chase Plain Toe Chukka Contemporary Fashion Boot

Black Nunn Bush Chase Plain Toe Chukka Contemporary Fashion Boot

+3

Brand Name: Nunn Bush
Product Name: Chase Plain Toe Chukka Contemporary Fashion Boot
Gender: Men's
Color: Black
Price: $64.95MSRP: $9532% OFF
Rating: 4Rated 4 stars out of 5(18)

Deer Stags - Garfield. Color Coffee. On sale for $63.43. MSRP $100.00. 37% off. 2.0 out of 5 stars

Brown Deer Stags Garfield

Brown Deer Stags Garfield

+3

Brand Name: Deer Stags
Product Name: Garfield
Gender: Men's
Color: Coffee
Price: $63.43MSRP: $10037% OFF
Rating: 2Rated 2 stars out of 5(2)

Cole Haan - Judson Grand Chukka Boots. Color Madeira/Dark Natural Water Resistant. Low Stock. On sale for $182.00. MSRP $260.00. 30% off.

Low Stock

Brown Cole Haan Judson Grand Chukka Boots

Brown Cole Haan Judson Grand Chukka Boots

+3

Brand Name: Cole Haan
Product Name: Judson Grand Chukka Boots
Gender: Men's
Color: Madeira/Dark Natural Water Resistant
Price: $182MSRP: $26030% OFF
Rating

Nunn Bush - Otto Plain Toe Chukka Boots. Color Black. On sale for $89.95. MSRP $120.00. 25% off. 4.1 out of 5 stars

Black Nunn Bush Otto Plain Toe Chukka Boots

Black Nunn Bush Otto Plain Toe Chukka Boots

+3

Brand Name: Nunn Bush
Product Name: Otto Plain Toe Chukka Boots
Gender: Men's
Color: Black
Price: $89.95MSRP: $12025% OFF
Rating: 4Rated 4 stars out of 5(33)

Ariat - Lookout. Color Foothill Brown. $159.95. 4.2 out of 5 stars

Brown Ariat Lookout

Brown Ariat Lookout

Brand Name: Ariat
Product Name: Lookout
Gender: Men's
Color: Foothill Brown
Price: $159.95
Rating: 4Rated 4 stars out of 5(141)

Cole Haan - Originalgrand Remastered Waterproof Chukka Boots. Color Black/Black. On sale for $140.00. MSRP $200.00. 30% off. 2.7 out of 5 stars

Black Cole Haan Originalgrand Remastered Waterproof Chukka Boots

Black Cole Haan Originalgrand Remastered Waterproof Chukka Boots

+2

Brand Name: Cole Haan
Product Name: Originalgrand Remastered Waterproof Chukka Boots
Gender: Men's
Color: Black/Black
Price: $140MSRP: $20030% OFF
Rating: 3Rated 3 stars out of 5(3)

Clarks - Desert Boots. Color Beeswax 1. $140.00. 4.4 out of 5 stars

Brown Clarks Desert Boots

Brown Clarks Desert Boots

+4

Brand Name: Clarks
Product Name: Desert Boots
Gender: Men's
Color: Beeswax 1
Price: $140
Rating: 4Rated 4 stars out of 5(780)

KEEN - KS Moc Chukka. Color Black/Black. On sale for $125.95. MSRP $139.95. 10% off.

Black KEEN KS Moc Chukka

Black KEEN KS Moc Chukka

Brand Name: KEEN
Product Name: KS Moc Chukka
Gender: Men's
Color: Black/Black
Price: $125.95MSRP: $139.9510% OFF
Rating

Deer Stags - Bangor. Color Black/Black. On sale for $54.00. MSRP $90.00. 40% off. 3.9 out of 5 stars

Black Deer Stags Bangor

Black Deer Stags Bangor

Brand Name: Deer Stags
Product Name: Bangor
Gender: Men's
Color: Black/Black
Price: $54MSRP: $9040% OFF
Rating: 4Rated 4 stars out of 5(14)

Eastland 1955 Edition - Seneca. Color Oak. $120.00. 4.4 out of 5 stars

Brown Eastland 1955 Edition Seneca

Brown Eastland 1955 Edition Seneca

+3

Brand Name: Eastland 1955 Edition
Product Name: Seneca
Gender: Men's
Color: Oak
Price: $120
Rating: 4Rated 4 stars out of 5(42)

Stacy Adams - Maxwell Plain Toe Demi Boot. Color Cognac. On sale for $93.50. MSRP $125.00. 25% off. 4.6 out of 5 stars

Tan Stacy Adams Maxwell Plain Toe Demi Boot

Tan Stacy Adams Maxwell Plain Toe Demi Boot

Brand Name: Stacy Adams
Product Name: Maxwell Plain Toe Demi Boot
Gender: Men's
Color: Cognac
Price: $93.50MSRP: $12525% OFF
Rating: 5Rated 5 stars out of 5(51)

Join Our Email List

Never miss out on latest drops & sales—plus, new subscribers get 10% off.*

*One code per email address.