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Boots on Sale $50 & Under

Shop Boots Deals

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mens rockport classic break chukka

28 items found

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Dr. Scholl's - Madison Men's Chukka. Color Mocha Taupe Textured Nubuck. Low Stock. On sale for $69.65. MSRP $115.00. 39% off. 5.0 out of 5 stars

Low Stock

Dr. Scholl's Madison Men's Chukka

Dr. Scholl's Madison Men's Chukka

Brand Name: Dr. Scholl's
Product Name: Madison Men's Chukka
Gender: Men's
Color: Mocha Taupe Textured Nubuck
Price: $69.65MSRP: $115

Sperry - Coldbay Chukka Realtree MM. Color Olive. On sale for $112.71. MSRP $120.00. 6% off.

Sperry Coldbay Chukka Realtree MM

Sperry Coldbay Chukka Realtree MM

Brand Name: Sperry
Product Name: Coldbay Chukka Realtree MM
Gender: Men's
Color: Olive
Price: $112.71MSRP: $120

Cole Haan - Originalgrand Remastered Waterproof Chukka Boots. Color Chocolate Raisin/Natural/Dark Sequoia Wp. Low Stock. On sale for $140.00. MSRP $200.00. 30% off. 2.2 out of 5 stars

Low Stock

Cole Haan Originalgrand Remastered Waterproof Chukka Boots

Cole Haan Originalgrand Remastered Waterproof Chukka Boots

Brand Name: Cole Haan
Product Name: Originalgrand Remastered Waterproof Chukka Boots
Gender: Men's
Color: Chocolate Raisin/Natural/Dark Sequoia Wp
Price: $140MSRP: $200

Cole Haan - Originalgrand Remastered Waterproof Chukka Boots. Color Scotch/Alabaster. Low Stock. On sale for $140.00. MSRP $200.00. 30% off. 2.2 out of 5 stars

Low Stock

Cole Haan Originalgrand Remastered Waterproof Chukka Boots

Cole Haan Originalgrand Remastered Waterproof Chukka Boots

Brand Name: Cole Haan
Product Name: Originalgrand Remastered Waterproof Chukka Boots
Gender: Men's
Color: Scotch/Alabaster
Price: $140MSRP: $200

Cole Haan - Originalgrand Remastered Waterproof Chukka Boots. Color Woodbury/Dark Roast. Low Stock. On sale for $100.00. MSRP $200.00. 50% off. 2.2 out of 5 stars

Low Stock

Cole Haan Originalgrand Remastered Waterproof Chukka Boots

Cole Haan Originalgrand Remastered Waterproof Chukka Boots

Brand Name: Cole Haan
Product Name: Originalgrand Remastered Waterproof Chukka Boots
Gender: Men's
Color: Woodbury/Dark Roast
Price: $100MSRP: $200

Johnston & Murphy - Upton Chukka. Color Navy Nubuck. Low Stock. On sale for $84.50. MSRP $169.00. 50% off. 4.1 out of 5 stars

Low Stock

Johnston & Murphy Upton Chukka

Johnston & Murphy Upton Chukka

Brand Name: Johnston & Murphy
Product Name: Upton Chukka
Gender: Men's
Color: Navy Nubuck
Price: $84.50MSRP: $169

The Original Muck Boot Company - Edgewater Classic. Color Black. Low Stock. On sale for $80.50. MSRP $115.00. 30% off. 3.0 out of 5 stars

Low Stock

The Original Muck Boot Company Edgewater Classic

The Original Muck Boot Company Edgewater Classic

Brand Name: The Original Muck Boot Company
Product Name: Edgewater Classic
Gender: Men's
Color: Black
Price: $80.50MSRP: $115

Clarks - Steadwell Mid. Color Black Leather. On sale for $87.00. MSRP $110.00. 21% off. 5.0 out of 5 stars

Clarks Steadwell Mid

Clarks Steadwell Mid

Brand Name: Clarks
Product Name: Steadwell Mid
Gender: Men's
Color: Black Leather
Price: $87MSRP: $110

Kenneth Cole - Vesto. Color Black. On sale for $83.30. MSRP $118.95. 30% off.

Kenneth Cole Vesto

Kenneth Cole Vesto

Brand Name: Kenneth Cole
Product Name: Vesto
Gender: Men's
Color: Black
Price: $83.30MSRP: $118.95

Kenneth Cole - Vesto. Color Medium Brown. On sale for $79.84. MSRP $118.95. 33% off.

Kenneth Cole Vesto

Kenneth Cole Vesto

Brand Name: Kenneth Cole
Product Name: Vesto
Gender: Men's
Color: Medium Brown
Price: $79.84MSRP: $118.95

Born - Ethan. Color Taupe (Avola). On sale for $88.40. MSRP $150.00. 41% off. 2.0 out of 5 stars

Born Ethan

Born Ethan

Brand Name: Born
Product Name: Ethan
Gender: Men's
Color: Taupe (Avola)
Price: $88.40MSRP: $150

Deer Stags - Bangor. Color Redwood/Dark Brown. On sale for $50.95. MSRP $90.00. 43% off. 3.9 out of 5 stars

Deer Stags Bangor

Deer Stags Bangor

Brand Name: Deer Stags
Product Name: Bangor
Gender: Men's
Color: Redwood/Dark Brown
Price: $50.95MSRP: $90

UGG - Neumel Crafted Regenerate. Color Chestnut. Low Stock. On sale for $105.00. MSRP $210.00. 50% off. 4.1 out of 5 stars

Low Stock

UGG Neumel Crafted Regenerate

UGG Neumel Crafted Regenerate

Brand Name: UGG
Product Name: Neumel Crafted Regenerate
Gender: Unisex
Color: Chestnut
Price: $105MSRP: $210

Dr. Martens - Bonny Chukka Boot. Color Black/Extra Tough Nylon/Rubbery. Low Stock. On sale for $108.00. MSRP $120.00. 10% off. 4.6 out of 5 stars

Low Stock

Dr. Martens Bonny Chukka Boot

Dr. Martens Bonny Chukka Boot

Brand Name: Dr. Martens
Product Name: Bonny Chukka Boot
Gender: Men's
Color: Black/Extra Tough Nylon/Rubbery
Price: $108MSRP: $120

Rockport - Total Motion Court T-Toe. Color White. Low Stock. On sale for $112.99. MSRP $120.00. 6% off. 5.0 out of 5 stars

Low Stock

Rockport Total Motion Court T-Toe

Rockport Total Motion Court T-Toe

Brand Name: Rockport
Product Name: Total Motion Court T-Toe
Gender: Men's
Color: White
Price: $112.99MSRP: $120

Rockport - Ports of Call Perth. Color Navy Blue Leather. On sale for $130.91. MSRP $150.00. 13% off. 4.2 out of 5 stars

Rockport Ports of Call Perth

Rockport Ports of Call Perth

Brand Name: Rockport
Product Name: Ports of Call Perth
Gender: Men's
Color: Navy Blue Leather
Price: $130.91MSRP: $150

Rockport - Ports of Call Perth. Color Tobacco. Low Stock. On sale for $115.22. MSRP $150.00. 23% off. 4.2 out of 5 stars

Low Stock

Rockport Ports of Call Perth

Rockport Ports of Call Perth

Brand Name: Rockport
Product Name: Ports of Call Perth
Gender: Men's
Color: Tobacco
Price: $115.22MSRP: $150

Rockport - Flynn. Color Medium Natural Leather. On sale for $103.96. MSRP $159.95. 35% off. 2.9 out of 5 stars

Rockport Flynn

Rockport Flynn

Brand Name: Rockport
Product Name: Flynn
Gender: Men's
Color: Medium Natural Leather
Price: $103.96MSRP: $159.95

Rockport - DMX Colby. Color White Leather. Low Stock. On sale for $82.47. MSRP $164.95. 50% off. 3.7 out of 5 stars

Low Stock

Rockport DMX Colby

Rockport DMX Colby

Brand Name: Rockport
Product Name: DMX Colby
Gender: Men's
Color: White Leather
Price: $82.47MSRP: $164.95

Rockport - Ports of Call Perth. Color Chocolate/Bark. Low Stock. On sale for $45.00. MSRP $150.00. 70% off. 4.2 out of 5 stars

Low Stock

Rockport Ports of Call Perth

Rockport Ports of Call Perth

Brand Name: Rockport
Product Name: Ports of Call Perth
Gender: Men's
Color: Chocolate/Bark
Price: $45MSRP: $150

Lucky Brand - Easy Rider Boot Premium Coolmax Stretch Jean. Color Dawson. Low Stock. On sale for $64.47. MSRP $129.00. 50% off. 3.7 out of 5 stars

Low Stock

Brand Name: Lucky Brand
Product Name: Easy Rider Boot Premium Coolmax Stretch Jean
Gender: Men's
Color: Dawson
Price: $64.47MSRP: $129

Rockport - Darwyn Fishermen. Color Brown II Leather. On sale for $89.95. MSRP $109.95. 18% off. 4.1 out of 5 stars

Rockport Darwyn Fishermen

Rockport Darwyn Fishermen

Brand Name: Rockport
Product Name: Darwyn Fishermen
Gender: Men's
Color: Brown II Leather
Price: $89.95MSRP: $109.95

Clarks - Wallaston Boot. Color Cola Suede. Low Stock. On sale for $97.50. MSRP $120.00. 19% off. 4.2 out of 5 stars

Low Stock

Clarks Wallaston Boot

Clarks Wallaston Boot

Brand Name: Clarks
Product Name: Wallaston Boot
Gender: Men's
Color: Cola Suede
Price: $97.50MSRP: $120

Clarks - Desert Trek. Color Beeswax. On sale for $120.59. MSRP $150.00. 20% off. 4.5 out of 5 stars

Clarks Desert Trek

Clarks Desert Trek

Brand Name: Clarks
Product Name: Desert Trek
Gender: Men's
Color: Beeswax
Price: $120.59MSRP: $150

Clarks - Relaxlite Moc. Color Cola Suede. Low Stock. On sale for $66.00. MSRP $110.00. 40% off. 5.0 out of 5 stars

Low Stock

Clarks Relaxlite Moc

Clarks Relaxlite Moc

Brand Name: Clarks
Product Name: Relaxlite Moc
Gender: Men's
Color: Cola Suede
Price: $66MSRP: $110

Clarks - Relaxlite Moc. Color Black Suede. Low Stock. On sale for $55.00. MSRP $110.00. 50% off. 5.0 out of 5 stars

Low Stock

Clarks Relaxlite Moc

Clarks Relaxlite Moc

Brand Name: Clarks
Product Name: Relaxlite Moc
Gender: Men's
Color: Black Suede
Price: $55MSRP: $110

Marc Joseph New York - Smith ST. Color Black Grainy/Suede. Low Stock. On sale for $78.00. MSRP $195.00. 60% off.

Low Stock

Marc Joseph New York Smith ST

Marc Joseph New York Smith ST

Brand Name: Marc Joseph New York
Product Name: Smith ST
Gender: Men's
Color: Black Grainy/Suede
Price: $78MSRP: $195

Rockport - Total Motion Leah Pump. Color Neutral Beige. Low Stock. On sale for $37.50. MSRP $125.00. 70% off. 3.6 out of 5 stars

Low Stock

Rockport Total Motion Leah Pump

Rockport Total Motion Leah Pump

Brand Name: Rockport
Product Name: Total Motion Leah Pump
Gender: Women's
Color: Neutral Beige
Price: $37.50MSRP: $125