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Boots on Sale $50 & Under

Shop Boots Deals

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Men's Textile Chukka Boots

15 items found

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Sperry - A/O Plushwave Lug Chukka. Color Black 2. Low Stock. On sale for $63.00. MSRP $140.00. 55% off. 4.1 out of 5 stars

Low Stock

Sperry A/O Plushwave Lug Chukka

Sperry A/O Plushwave Lug Chukka

Brand Name: Sperry
Product Name: A/O Plushwave Lug Chukka
Gender: Men's
Color: Black 2
Price: $63MSRP: $140

Stacy Adams - Maxwell Plain Toe Demi Boot. Color Cognac. On sale for $88.00. MSRP $125.00. 30% 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: $88MSRP: $125

ECCO - Grainer Chukka Boot. Color Camel. On sale for $142.26. MSRP $190.00. 25% off. 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: $142.26MSRP: $190

Clarks - Whiddon Mid. Color Mahogany Leather. Low Stock. On sale for $87.96. MSRP $110.00. 20% off. 3.4 out of 5 stars

Low Stock

Clarks Whiddon Mid

Clarks Whiddon Mid

Brand Name: Clarks
Product Name: Whiddon Mid
Gender: Men's
Color: Mahogany Leather
Price: $87.96MSRP: $110

Ben Sherman - Dirk Chukka. Color Tan PU. Low Stock. On sale for $84.00. MSRP $120.00. 30% off.

Low Stock

Ben Sherman Dirk Chukka

Ben Sherman Dirk Chukka

Brand Name: Ben Sherman
Product Name: Dirk Chukka
Gender: Men's
Color: Tan PU
Price: $84MSRP: $120

Blake McKay - Alder. Color Tan. Low Stock. On sale for $74.25. MSRP $165.00. 55% off.

Low Stock

Blake McKay Alder

Blake McKay Alder

Brand Name: Blake McKay
Product Name: Alder
Gender: Men's
Color: Tan
Price: $74.25MSRP: $165

Nunn Bush - Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology. Color Black Tumbled. Low Stock. On sale for $106.59. MSRP $115.00. 7% off. 4.3 out of 5 stars

Low Stock

Nunn Bush Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology

Nunn Bush Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology

Brand Name: Nunn Bush
Product Name: Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology
Gender: Men's
Color: Black Tumbled
Price: $106.59MSRP: $115

Nunn Bush - Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology. Color Brown CH. Low Stock. On sale for $100.06. MSRP $115.00. 13% off. 4.3 out of 5 stars

Low Stock

Nunn Bush Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology

Nunn Bush Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology

Brand Name: Nunn Bush
Product Name: Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology
Gender: Men's
Color: Brown CH
Price: $100.06MSRP: $115

Steve Madden - Hestonn - Extended Sizes. Color Tan Leather. On sale for $63.00. MSRP $99.99. 37% off. 3.9 out of 5 stars

Steve Madden Hestonn - Extended Sizes

Steve Madden Hestonn - Extended Sizes

Brand Name: Steve Madden
Product Name: Hestonn - Extended Sizes
Gender: Men's
Color: Tan Leather
Price: $63MSRP: $99.99

Steve Madden - Harken - Extended Sizes. Color Black. Low Stock. On sale for $67.38. MSRP $99.99. 33% 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: $67.38MSRP: $99.99

Cole Haan - Berkshire Chelsea Boots. Color Pavement Nubuck/Demitasse Water Resistant. Low Stock. $220.00. 4.5 out of 5 stars

Low Stock

Cole Haan Berkshire Chelsea Boots

Cole Haan Berkshire Chelsea Boots

Brand Name: Cole Haan
Product Name: Berkshire Chelsea Boots
Gender: Men's
Color: Pavement Nubuck/Demitasse Water Resistant
Price: $220

Cole Haan - Berkshire Chelsea Boots. Color British Tan/C. On sale for $253.89. MSRP $260.00. 2% off. 4.5 out of 5 stars

Cole Haan Berkshire Chelsea Boots

Cole Haan Berkshire Chelsea Boots

Brand Name: Cole Haan
Product Name: Berkshire Chelsea Boots
Gender: Men's
Color: British Tan/C
Price: $253.89MSRP: $260

Cole Haan - Berkshire Chelsea Boots. Color Lava Suede/Dark. On sale for $221.57. MSRP $250.00. 11% off. 4.5 out of 5 stars

Cole Haan Berkshire Chelsea Boots

Cole Haan Berkshire Chelsea Boots

Brand Name: Cole Haan
Product Name: Berkshire Chelsea Boots
Gender: Men's
Color: Lava Suede/Dark
Price: $221.57MSRP: $250

Propet - Findley. Color Tan. Low Stock. On sale for $91.96. MSRP $134.99. 32% off. 3.6 out of 5 stars

Low Stock

Propet Findley

Propet Findley

Brand Name: Propet
Product Name: Findley
Gender: Men's
Color: Tan
Price: $91.96MSRP: $134.99

Johnston & Murphy - Braydon Chukka. Color Charcoal Waxed Suede. Low Stock. On sale for $134.10. MSRP $149.00. 10% off.

Low Stock

Johnston & Murphy Braydon Chukka

Johnston & Murphy Braydon Chukka

Brand Name: Johnston & Murphy
Product Name: Braydon Chukka
Gender: Men's
Color: Charcoal Waxed Suede
Price: $134.10MSRP: $149