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Boots on Sale $50 & Under

Shop Boots Deals

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Chukka Boots

27 items found

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Johnston & Murphy - Brody Chukka. Color Snuff Suede. Low Stock. On sale for $49.50. MSRP $165.00. 70% off.

Low Stock

Johnston & Murphy Brody Chukka

Johnston & Murphy Brody Chukka

Brand Name: Johnston & Murphy
Product Name: Brody Chukka
Gender: Men's
Color: Snuff Suede
Price: $49.50MSRP: $165

Clarks - Shepton. Color Sand Suede. On sale for $61.39. MSRP $110.00. 44% off. 1.7 out of 5 stars

Clarks Shepton

Clarks Shepton

Brand Name: Clarks
Product Name: Shepton
Gender: Men's
Color: Sand Suede
Price: $61.39MSRP: $110

Cole Haan - Grand Remix Chukka. Color Morel Nubuck/Ivory. Low Stock. On sale for $77.00. MSRP $140.00. 45% off. 4.3 out of 5 stars

Low Stock

Cole Haan Grand Remix Chukka

Cole Haan Grand Remix Chukka

Brand Name: Cole Haan
Product Name: Grand Remix Chukka
Gender: Men's
Color: Morel Nubuck/Ivory
Price: $77MSRP: $140

Johnston & Murphy - Barrett Chukka. Color Tan Full Grain. Low Stock. On sale for $52.50. MSRP $175.00. 70% off.

Low Stock

Johnston & Murphy Barrett Chukka

Johnston & Murphy Barrett Chukka

Brand Name: Johnston & Murphy
Product Name: Barrett Chukka
Gender: Men's
Color: Tan Full Grain
Price: $52.50MSRP: $175

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

Sperry Newton Boots

Sperry Newton Boots

Brand Name: Sperry
Product Name: Newton Boots
Gender: Men's
Color: Taupe
Price: $148.50MSRP: $165

Steve Madden - Daviston. Color Brown. On sale for $129.27. MSRP $165.00. 22% off.

Steve Madden Daviston

Steve Madden Daviston

Brand Name: Steve Madden
Product Name: Daviston
Gender: Men's
Color: Brown
Price: $129.27MSRP: $165

Deer Stags - Bangor. Color Redwood/Dark Brown. On sale for $48.67. MSRP $90.00. 46% 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: $48.67MSRP: $90

Cole Haan - Originalgrand Remastered Waterproof Chukka Boots. Color Scotch/Alabaster. Low Stock. On sale for $194.25. MSRP $200.00. 3% off. 2.7 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: $194.25MSRP: $200

Cole Haan - Originalgrand Remastered Waterproof Chukka Boots. Color Woodbury/Dark Roast. Low Stock. On sale for $160.00. MSRP $200.00. 20% off. 2.7 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: $160MSRP: $200

Cole Haan - Originalgrand Remastered Waterproof Chukka Boots. Color Chocolate Raisin/Natural/Dark Sequoia Wp. Low Stock. On sale for $180.00. MSRP $200.00. 10% off. 2.7 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: $180MSRP: $200

Cole Haan - Morse Grand Chukka Boots. Color Morel Suede/Ivory. Low Stock. On sale for $103.60. MSRP $148.00. 30% off.

Low Stock

Cole Haan Morse Grand Chukka Boots

Cole Haan Morse Grand Chukka Boots

Brand Name: Cole Haan
Product Name: Morse Grand Chukka Boots
Gender: Men's
Color: Morel Suede/Ivory
Price: $103.60MSRP: $148

Steve Madden - Harken - Extended Sizes. Color Black. Low Stock. On sale for $94.15. MSRP $109.99. 14% off. 4.1 out of 5 stars

Low Stock

Steve Madden Harken - Extended Sizes

Steve Madden Harken - Extended Sizes

Brand Name: Steve Madden
Product Name: Harken - Extended Sizes
Gender: Men's
Color: Black
Price: $94.15MSRP: $109.99

Johnston & Murphy - Calder Chukka. Color Mahogany Full Grain. On sale for $140.25. MSRP $165.00. 15% off. 4.0 out of 5 stars

Johnston & Murphy Calder Chukka

Johnston & Murphy Calder Chukka

Brand Name: Johnston & Murphy
Product Name: Calder Chukka
Gender: Men's
Color: Mahogany Full Grain
Price: $140.25MSRP: $165

Johnston & Murphy - Brody Chukka. Color Brown Hand-Stained Calfskin. Low Stock. On sale for $82.50. MSRP $165.00. 50% off.

Low Stock

Johnston & Murphy Brody Chukka

Johnston & Murphy Brody Chukka

Brand Name: Johnston & Murphy
Product Name: Brody Chukka
Gender: Men's
Color: Brown Hand-Stained Calfskin
Price: $82.50MSRP: $165

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

Low Stock

Clarks Steadwell Mid

Clarks Steadwell Mid

Brand Name: Clarks
Product Name: Steadwell Mid
Gender: Men's
Color: Black Leather
Price: $99MSRP: $110

Dr. Scholl's - Madison Men's Chukka. Color Mocha Taupe Textured Nubuck. Low Stock. On sale for $71.16. MSRP $115.00. 38% 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: $71.16MSRP: $115

Johnston & Murphy - Bolivar Plain Toe Boots. Color Snuff Italian Suede. Low Stock. On sale for $114.00. MSRP $285.00. 60% off.

Low Stock

Johnston & Murphy Bolivar Plain Toe Boots

Johnston & Murphy Bolivar Plain Toe Boots

Brand Name: Johnston & Murphy
Product Name: Bolivar Plain Toe Boots
Gender: Men's
Color: Snuff Italian Suede
Price: $114MSRP: $285

Johnston & Murphy - Dudley Chukka. Color Brown Waxed English Suede. Low Stock. On sale for $82.50. MSRP $275.00. 70% off.

Low Stock

Johnston & Murphy Dudley Chukka

Johnston & Murphy Dudley Chukka

Brand Name: Johnston & Murphy
Product Name: Dudley Chukka
Gender: Men's
Color: Brown Waxed English Suede
Price: $82.50MSRP: $275

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

Sperry Mini Lug Chukka

Sperry Mini Lug Chukka

Brand Name: Sperry
Product Name: Mini Lug Chukka
Gender: Men's
Color: Other Brown
Price: $105MSRP: $150

Steve Madden - Daviston. Color Black. On sale for $125.59. MSRP $165.00. 24% off.

Steve Madden Daviston

Steve Madden Daviston

Brand Name: Steve Madden
Product Name: Daviston
Gender: Men's
Color: Black
Price: $125.59MSRP: $165

Cole Haan - Berkshire Lug Chukka Boots. Color British Tan/C. Low Stock. On sale for $234.00. MSRP $260.00. 10% off. 4.5 out of 5 stars

Low Stock

Cole Haan Berkshire Lug Chukka Boots

Cole Haan Berkshire Lug Chukka Boots

Brand Name: Cole Haan
Product Name: Berkshire Lug Chukka Boots
Gender: Men's
Color: British Tan/C
Price: $234MSRP: $260

Born - Theo. Color Black. Low Stock. On sale for $71.50. MSRP $130.00. 45% off. 5.0 out of 5 stars

Low Stock

Born Theo

Born Theo

Brand Name: Born
Product Name: Theo
Gender: Men's
Color: Black
Price: $71.50MSRP: $130

Steve Madden - Palta. Color Sand. Low Stock. On sale for $65.00. MSRP $130.00. 50% off.

Low Stock

Steve Madden Palta

Steve Madden Palta

Brand Name: Steve Madden
Product Name: Palta
Gender: Men's
Color: Sand
Price: $65MSRP: $130

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

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: $93.50MSRP: $125

Johnston & Murphy - Upton Chukka Boots. Color Tan Full Grain. On sale for $152.10. MSRP $169.00. 10% off. 4.7 out of 5 stars

Johnston & Murphy Upton Chukka Boots

Johnston & Murphy Upton Chukka Boots

Brand Name: Johnston & Murphy
Product Name: Upton Chukka Boots
Gender: Men's
Color: Tan Full Grain
Price: $152.10MSRP: $169

ECCO - Metropole Milan Chukka Boots. Color Camel Suede. On sale for $137.00. MSRP $194.95. 30% off. 4.0 out of 5 stars

ECCO Metropole Milan Chukka Boots

ECCO Metropole Milan Chukka Boots

Brand Name: ECCO
Product Name: Metropole Milan Chukka Boots
Gender: Men's
Color: Camel Suede
Price: $137MSRP: $194.95

ECCO - London Lace Up Waterproof Chukka Boots. Color Cocoa Brown Nubuck. Low Stock. On sale for $195.45. MSRP $229.95. 15% off. 4.0 out of 5 stars

Low Stock

ECCO London Lace Up Waterproof Chukka Boots

ECCO London Lace Up Waterproof Chukka Boots

Brand Name: ECCO
Product Name: London Lace Up Waterproof Chukka Boots
Gender: Men's
Color: Cocoa Brown Nubuck
Price: $195.45MSRP: $229.95