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Boots on Sale $50 or Less!

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Men Chukka Boots

48 items found

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Stacy Adams - Martindale Chukka Boot. Color Bordeaux. On sale for $97.50. MSRP $130.00.. 4.0 out of 5 stars

Stacy Adams Martindale Chukka Boot

Stacy Adams Martindale Chukka Boot

Brand Name: Stacy Adams
Product Name: Martindale Chukka Boot
Gender: Men's
Color: Bordeaux
Price: $97.50MSRP: $130.00

Stacy Adams - Maxwell Plain Toe Demi Boot. Color Cognac. On sale for $99.00. MSRP $125.00.. 4.8 out of 5 stars

Stacy Adams Maxwell Plain Toe Demi Boot

Stacy Adams Maxwell Plain Toe Demi Boot

Brand Name: Stacy Adams
Product Name: Maxwell Plain Toe Demi Boot
Gender: Men's
Color: Cognac
Price: $99.00MSRP: $125.00

ECCO - London Plain Toe Chukka Boots. Color Cognac. On sale for $149.99. MSRP $225.00..

ECCO London Plain Toe Chukka Boots

ECCO London Plain Toe Chukka Boots

Brand Name: ECCO
Product Name: London Plain Toe Chukka Boots
Gender: Men's
Color: Cognac
Price: $149.99MSRP: $225.00

ECCO - Grainer Chukka Boot. Color Camel. On sale for $150.29. MSRP $190.00.. 2.5 out of 5 stars

ECCO Grainer Chukka Boot

ECCO Grainer Chukka Boot

Brand Name: ECCO
Product Name: Grainer Chukka Boot
Gender: Men's
Color: Camel
Price: $150.29MSRP: $190.00

Bruno Magli - Taddeo. Color Taupe Suede. Low Stock. On sale for $168.75. MSRP $375.00..

Low Stock

Bruno Magli Taddeo

Bruno Magli Taddeo

Brand Name: Bruno Magli
Product Name: Taddeo
Gender: Men's
Color: Taupe Suede
Price: $168.75MSRP: $375.00

Cole Haan - Berkshire Lug Chukka Boot. Color Lava Suede/Dark. On sale for $187.50. MSRP $250.00.. 4.7 out of 5 stars

Cole Haan Berkshire Lug Chukka Boot

Cole Haan Berkshire Lug Chukka Boot

Brand Name: Cole Haan
Product Name: Berkshire Lug Chukka Boot
Gender: Men's
Color: Lava Suede/Dark
Price: $187.50MSRP: $250.00

Steve Madden - Yvor. Color Grey Suede. Low Stock. On sale for $105.00. MSRP $140.00.. 2.0 out of 5 stars

Low Stock

Steve Madden Yvor

Steve Madden Yvor

Brand Name: Steve Madden
Product Name: Yvor
Gender: Men's
Color: Grey Suede
Price: $105.00MSRP: $140.00

Cole Haan - Berkshire Lug Chukka Boot. Color Bloodstone/Dark Natural Water Resistant. On sale for $144.00. MSRP $240.00.. 4.7 out of 5 stars

Cole Haan Berkshire Lug Chukka Boot

Cole Haan Berkshire Lug Chukka Boot

Brand Name: Cole Haan
Product Name: Berkshire Lug Chukka Boot
Gender: Men's
Color: Bloodstone/Dark Natural Water Resistant
Price: $144.00MSRP: $240.00

Frye - Bowery Chukka. Color Cognac. Low Stock. On sale for $245.96. MSRP $328.00.. 3.5 out of 5 stars

Low Stock

Frye Bowery Chukka

Frye Bowery Chukka

Brand Name: Frye
Product Name: Bowery Chukka
Gender: Men's
Color: Cognac
Price: $245.96MSRP: $328.00

Frye - Bowery Chukka. Color Black. Low Stock. On sale for $232.84. MSRP $328.00.. 3.5 out of 5 stars

Low Stock

Frye Bowery Chukka

Frye Bowery Chukka

Brand Name: Frye
Product Name: Bowery Chukka
Gender: Men's
Color: Black
Price: $232.84MSRP: $328.00

Allen Edmonds - Graham Moccasins. Color Snuff Suede. Low Stock. On sale for $321.75. MSRP $495.00..

Low Stock

Allen Edmonds Graham Moccasins

Allen Edmonds Graham Moccasins

Brand Name: Allen Edmonds
Product Name: Graham Moccasins
Gender: Men's
Color: Snuff Suede
Price: $321.75MSRP: $495.00

SOREL - Carson™ Chukka WP. Color Blackened Brown/Khaki. On sale for $102.36. MSRP $160.00.. 4.0 out of 5 stars

SOREL Carson™ Chukka WP

SOREL Carson™ Chukka WP

Brand Name: SOREL
Product Name: Carson™ Chukka WP
Gender: Men's
Color: Blackened Brown/Khaki
Price: $102.36MSRP: $160.00

Johnston & Murphy Collection - Dudley Chukka. Color Brown Waxed English Suede. On sale for $189.75. MSRP $275.00..

Johnston & Murphy Collection Dudley Chukka

Johnston & Murphy Collection Dudley Chukka

Brand Name: Johnston & Murphy Collection
Product Name: Dudley Chukka
Gender: Men's
Color: Brown Waxed English Suede
Price: $189.75MSRP: $275.00

Propet - Findley. Color Black. On sale for $95.00. MSRP $134.95.. 3.6 out of 5 stars

Propet Findley

Propet Findley

Brand Name: Propet
Product Name: Findley
Gender: Men's
Color: Black
Price: $95.00MSRP: $134.95

Allen Edmonds - Chandler. Color Teak. On sale for $430.65. MSRP $495.00.. 4.4 out of 5 stars

Allen Edmonds Chandler

Allen Edmonds Chandler

Brand Name: Allen Edmonds
Product Name: Chandler
Gender: Men's
Color: Teak
Price: $430.65MSRP: $495.00

Stacy Adams - Kyron Chukka Boot. Color Black Smooth. Low Stock. On sale for $77.49. MSRP $115.00.. 3.5 out of 5 stars

Low Stock

Stacy Adams Kyron Chukka Boot

Stacy Adams Kyron Chukka Boot

Brand Name: Stacy Adams
Product Name: Kyron Chukka Boot
Gender: Men's
Color: Black Smooth
Price: $77.49MSRP: $115.00

Stacy Adams - Kyron Chukka Boot. Color Brown Multi. Low Stock. On sale for $34.90. MSRP $115.00.. 3.5 out of 5 stars

Low Stock

Stacy Adams Kyron Chukka Boot

Stacy Adams Kyron Chukka Boot

Brand Name: Stacy Adams
Product Name: Kyron Chukka Boot
Gender: Men's
Color: Brown Multi
Price: $34.90MSRP: $115.00

Rockport - Berenger Plain Toe Chukka. Color Tan. Low Stock. On sale for $99.57. MSRP $119.95.. 3.5 out of 5 stars

Low Stock

Rockport Berenger Plain Toe Chukka

Rockport Berenger Plain Toe Chukka

Brand Name: Rockport
Product Name: Berenger Plain Toe Chukka
Gender: Men's
Color: Tan
Price: $99.57MSRP: $119.95

Rockport - Style Leader 2 Chukka. Color Black. Low Stock. On sale for $112.45. MSRP $124.95.. 3.7 out of 5 stars

Low Stock

Rockport Style Leader 2 Chukka

Rockport Style Leader 2 Chukka

Brand Name: Rockport
Product Name: Style Leader 2 Chukka
Gender: Men's
Color: Black
Price: $112.45MSRP: $124.95

Stacy Adams - Martfield Chukka Boot. Color Mocha. Low Stock. On sale for $114.40. MSRP $130.00.. 5.0 out of 5 stars

Low Stock

Stacy Adams Martfield Chukka Boot

Stacy Adams Martfield Chukka Boot

Brand Name: Stacy Adams
Product Name: Martfield Chukka Boot
Gender: Men's
Color: Mocha
Price: $114.40MSRP: $130.00

Stacy Adams - Martfield Chukka Boot. Color Dark Gray. Low Stock. On sale for $97.50. MSRP $130.00.. 5.0 out of 5 stars

Low Stock

Stacy Adams Martfield Chukka Boot

Stacy Adams Martfield Chukka Boot

Brand Name: Stacy Adams
Product Name: Martfield Chukka Boot
Gender: Men's
Color: Dark Gray
Price: $97.50MSRP: $130.00

Stacy Adams - Martfield Chukka Boot. Color Sand. Low Stock. On sale for $84.50. MSRP $130.00.. 5.0 out of 5 stars

Low Stock

Stacy Adams Martfield Chukka Boot

Stacy Adams Martfield Chukka Boot

Brand Name: Stacy Adams
Product Name: Martfield Chukka Boot
Gender: Men's
Color: Sand
Price: $84.50MSRP: $130.00

Rockport - Total Motion Dressport Chukka. Color British Tan. Low Stock. On sale for $95.20. MSRP $140.00.. 4.2 out of 5 stars

Low Stock

Rockport Total Motion Dressport Chukka

Rockport Total Motion Dressport Chukka

Brand Name: Rockport
Product Name: Total Motion Dressport Chukka
Gender: Men's
Color: British Tan
Price: $95.20MSRP: $140.00

Johnston & Murphy - XC Flex Raleigh Chukka. Color Tan Full Grain. Low Stock. On sale for $110.25. MSRP $175.00.. 4.3 out of 5 stars

Low Stock

Johnston & Murphy XC Flex Raleigh Chukka

Johnston & Murphy XC Flex Raleigh Chukka

Brand Name: Johnston & Murphy
Product Name: XC Flex Raleigh Chukka
Gender: Men's
Color: Tan Full Grain
Price: $110.25MSRP: $175.00

Marc Joseph New York - Vestry. Color Black Calf Leather. Low Stock. On sale for $124.80. MSRP $195.00.. 5.0 out of 5 stars

Low Stock

Marc Joseph New York Vestry

Marc Joseph New York Vestry

Brand Name: Marc Joseph New York
Product Name: Vestry
Gender: Men's
Color: Black Calf Leather
Price: $124.80MSRP: $195.00

Marc Joseph New York - Vestry. Color Brown Napa. Low Stock. On sale for $78.00. MSRP $195.00.. 5.0 out of 5 stars

Low Stock

Marc Joseph New York Vestry

Marc Joseph New York Vestry

Brand Name: Marc Joseph New York
Product Name: Vestry
Gender: Men's
Color: Brown Napa
Price: $78.00MSRP: $195.00

Marc Joseph New York - Lenox Ave. Color Black Grainy. Low Stock. On sale for $115.05. MSRP $195.00.. 3.3 out of 5 stars

Low Stock

Marc Joseph New York Lenox Ave

Marc Joseph New York Lenox Ave

Brand Name: Marc Joseph New York
Product Name: Lenox Ave
Gender: Men's
Color: Black Grainy
Price: $115.05MSRP: $195.00

Marc Joseph New York - Lenox Ave. Color Havana Grainy. Low Stock. On sale for $83.85. MSRP $195.00.. 3.3 out of 5 stars

Low Stock

Marc Joseph New York Lenox Ave

Marc Joseph New York Lenox Ave

Brand Name: Marc Joseph New York
Product Name: Lenox Ave
Gender: Men's
Color: Havana Grainy
Price: $83.85MSRP: $195.00

Johnston & Murphy Collection - Welch Chukka. Color Gray Suede. Low Stock. On sale for $190.80. MSRP $265.00.. 4.5 out of 5 stars

Low Stock

Johnston & Murphy Collection Welch Chukka

Johnston & Murphy Collection Welch Chukka

Brand Name: Johnston & Murphy Collection
Product Name: Welch Chukka
Gender: Men's
Color: Gray Suede
Price: $190.80MSRP: $265.00

Clarks - Corston DB Waterproof. Color Brown Leather Waterproof. Low Stock. On sale for $113.51. MSRP $170.00.. 5.0 out of 5 stars

Low Stock

Clarks Corston DB Waterproof

Clarks Corston DB Waterproof

Brand Name: Clarks
Product Name: Corston DB Waterproof
Gender: Men's
Color: Brown Leather Waterproof
Price: $113.51MSRP: $170.00

Clarks - Corston Wally Waterproof. Color Black Leather Waterproof. Low Stock. On sale for $88.00. MSRP $170.00.. 3.0 out of 5 stars

Low Stock

Clarks Corston Wally Waterproof

Clarks Corston Wally Waterproof

Brand Name: Clarks
Product Name: Corston Wally Waterproof
Gender: Men's
Color: Black Leather Waterproof
Price: $88.00MSRP: $170.00

Clarks - Corston Wally Waterproof. Color Olive Leather Waterproof. Low Stock. On sale for $76.47. MSRP $170.00.. 3.0 out of 5 stars

Low Stock

Clarks Corston Wally Waterproof

Clarks Corston Wally Waterproof

Brand Name: Clarks
Product Name: Corston Wally Waterproof
Gender: Men's
Color: Olive Leather Waterproof
Price: $76.47MSRP: $170.00

Gordon Rush - Austin. Color Espresso. Low Stock. $180.20. 3.0 out of 5 stars

Low Stock

Gordon Rush Austin

Gordon Rush Austin

Brand Name: Gordon Rush
Product Name: Austin
Gender: Men's
Color: Espresso
Price: $180.20

Tommy Hilfiger - Natash. Color Black. Low Stock. On sale for $65.40. MSRP $109.00..

Low Stock

Tommy Hilfiger Natash

Tommy Hilfiger Natash

Brand Name: Tommy Hilfiger
Product Name: Natash
Gender: Men's
Color: Black
Price: $65.40MSRP: $109.00

Tommy Hilfiger - Natash. Color Brown. Low Stock. On sale for $65.40. MSRP $109.00..

Low Stock

Tommy Hilfiger Natash

Tommy Hilfiger Natash

Brand Name: Tommy Hilfiger
Product Name: Natash
Gender: Men's
Color: Brown
Price: $65.40MSRP: $109.00

Blake McKay - Alder. Color Tan. Low Stock. On sale for $80.85. MSRP $165.00..

Low Stock

Blake McKay Alder

Blake McKay Alder

Brand Name: Blake McKay
Product Name: Alder
Gender: Men's
Color: Tan
Price: $80.85MSRP: $165.00

Blake McKay - Alder. Color Black. Low Stock. On sale for $74.25. MSRP $165.00..

Low Stock

Blake McKay Alder

Blake McKay Alder

Brand Name: Blake McKay
Product Name: Alder
Gender: Men's
Color: Black
Price: $74.25MSRP: $165.00

Allen Edmonds - Graham Moccasins. Color Loden Suede. Low Stock. On sale for $350.00. MSRP $495.00..

Low Stock

Allen Edmonds Graham Moccasins

Allen Edmonds Graham Moccasins

Brand Name: Allen Edmonds
Product Name: Graham Moccasins
Gender: Men's
Color: Loden Suede
Price: $350.00MSRP: $495.00

Massimo Matteo - Chukka Classic Boots. Color Black Nubuck. Low Stock. On sale for $59.81. MSRP $94.95.. 4.5 out of 5 stars

Low Stock

Massimo Matteo Chukka Classic Boots

Massimo Matteo Chukka Classic Boots

Brand Name: Massimo Matteo
Product Name: Chukka Classic Boots
Gender: Men's
Color: Black Nubuck
Price: $59.81MSRP: $94.95

Massimo Matteo - Chukka Classic Boots. Color Crème Nubuck. Low Stock. On sale for $50.32. MSRP $94.95.. 4.5 out of 5 stars

Low Stock

Massimo Matteo Chukka Classic Boots

Massimo Matteo Chukka Classic Boots

Brand Name: Massimo Matteo
Product Name: Chukka Classic Boots
Gender: Men's
Color: Crème Nubuck
Price: $50.32MSRP: $94.95

Massimo Matteo - Chukka Classic Boots. Color Cafe Nubuck. Low Stock. On sale for $71.21. MSRP $94.95.. 4.5 out of 5 stars

Low Stock

Massimo Matteo Chukka Classic Boots

Massimo Matteo Chukka Classic Boots

Brand Name: Massimo Matteo
Product Name: Chukka Classic Boots
Gender: Men's
Color: Cafe Nubuck
Price: $71.21MSRP: $94.95

Propet - Findley. Color Tan. Low Stock. On sale for $95.00. MSRP $134.95.. 3.6 out of 5 stars

Low Stock

Propet Findley

Propet Findley

Brand Name: Propet
Product Name: Findley
Gender: Men's
Color: Tan
Price: $95.00MSRP: $134.95

Vince Camuto - Leandro. Color Cognac/Mocca. Low Stock. On sale for $119.25. MSRP $159.00..

Low Stock

Vince Camuto Leandro

Vince Camuto Leandro

Brand Name: Vince Camuto
Product Name: Leandro
Gender: Men's
Color: Cognac/Mocca
Price: $119.25MSRP: $159.00

Allen Edmonds - Chandler. Color Loden. Low Stock. On sale for $223.25. MSRP $475.00.. 4.4 out of 5 stars

Low Stock

Allen Edmonds Chandler

Allen Edmonds Chandler

Brand Name: Allen Edmonds
Product Name: Chandler
Gender: Men's
Color: Loden
Price: $223.25MSRP: $475.00

Martin Dingman - Ernest Kudu. Color Evergreen. Low Stock. On sale for $229.10. MSRP $395.00..

Low Stock

Martin Dingman Ernest Kudu

Martin Dingman Ernest Kudu

Brand Name: Martin Dingman
Product Name: Ernest Kudu
Gender: Men's
Color: Evergreen
Price: $229.10MSRP: $395.00

SOREL - Carson™ Chukka WP. Color Major/Wet Sand. On sale for $95.97. MSRP $160.00.. 4.0 out of 5 stars

SOREL Carson™ Chukka WP

SOREL Carson™ Chukka WP

Brand Name: SOREL
Product Name: Carson™ Chukka WP
Gender: Men's
Color: Major/Wet Sand
Price: $95.97MSRP: $160.00

SOREL - Carson™ Chukka WP. Color Elk/Oatmeal. On sale for $95.97. MSRP $160.00.. 4.0 out of 5 stars

SOREL Carson™ Chukka WP

SOREL Carson™ Chukka WP

Brand Name: SOREL
Product Name: Carson™ Chukka WP
Gender: Men's
Color: Elk/Oatmeal
Price: $95.97MSRP: $160.00

Johnston & Murphy Collection - Dudley Chukka. Color Tan Dip-Dyed Calfskin. Low Stock. On sale for $151.25. MSRP $275.00..

Low Stock

Johnston & Murphy Collection Dudley Chukka

Johnston & Murphy Collection Dudley Chukka

Brand Name: Johnston & Murphy Collection
Product Name: Dudley Chukka
Gender: Men's
Color: Tan Dip-Dyed Calfskin
Price: $151.25MSRP: $275.00