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Boots on Sale $50 & Under

Shop Boots Deals

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Size 9.5 Casual Chukka Boots

13 items found

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Eastland 1955 Edition - Hugo. Color Black. Low Stock. On sale for $34.97. MSRP $100.00. 65% off.

Low Stock

Eastland 1955 Edition Hugo

Eastland 1955 Edition Hugo

Brand Name: Eastland 1955 Edition
Product Name: Hugo
Gender: Men's
Color: Black
Price: $34.97MSRP: $100

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

Steve Madden - Palta. Color Sand. On sale for $122.83. MSRP $130.00. 6% off.

Steve Madden Palta

Steve Madden Palta

Brand Name: Steve Madden
Product Name: Palta
Gender: Men's
Color: Sand
Price: $122.83MSRP: $130

The North Face - Never Stop Exploring Chukka Suede. Color Almond Butter/Warm Sand. On sale for $93.75. MSRP $125.00. 25% off. 4.1 out of 5 stars

The North Face Never Stop Exploring Chukka Suede

The North Face Never Stop Exploring Chukka Suede

Brand Name: The North Face
Product Name: Never Stop Exploring Chukka Suede
Gender: Men's
Color: Almond Butter/Warm Sand
Price: $93.75MSRP: $125

Gordon Rush - Austin. Color Espresso. Low Stock. $145.75. 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: $145.75

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

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: $253.89MSRP: $260

Dr. Scholl's - Madison Men's Chukka. Color Mocha Taupe Textured Nubuck. Low Stock. On sale for $106.86. MSRP $115.00. 7% 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: $106.86MSRP: $115

Dr. Scholl's - Madison Men's Chukka. Color Dark Grey Textured Nubuck. Low Stock. On sale for $103.50. MSRP $115.00. 10% 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: Dark Grey Textured Nubuck
Price: $103.50MSRP: $115

Dr. Scholl's - Manchester. Color Grey Faux Leather. Low Stock. On sale for $60.00. MSRP $120.00. 50% off. 3.0 out of 5 stars

Low Stock

Dr. Scholl's Manchester

Dr. Scholl's Manchester

Brand Name: Dr. Scholl's
Product Name: Manchester
Gender: Men's
Color: Grey Faux Leather
Price: $60MSRP: $120

SOREL - Carson™ Chukka WP. Color Blackened Brown/Khaki. On sale for $80.00. MSRP $160.00. 50% off. 3.8 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: $80MSRP: $160

Polo Ralph Lauren - Talan Chukka Boot. Color Defender Green. On sale for $114.42. MSRP $138.00. 17% off. 4.2 out of 5 stars

Polo Ralph Lauren Talan Chukka Boot

Polo Ralph Lauren Talan Chukka Boot

Brand Name: Polo Ralph Lauren
Product Name: Talan Chukka Boot
Gender: Men's
Color: Defender Green
Price: $114.42MSRP: $138

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

Sperry - Cold Bay Chukka Realtree. Color Olive. $118.84.

Sperry Cold Bay Chukka Realtree

Sperry Cold Bay Chukka Realtree

Brand Name: Sperry
Product Name: Cold Bay Chukka Realtree
Gender: Men's
Color: Olive
Price: $118.84