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Boots on Sale $50 & Under

Shop Boots Deals

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Size 9.5 Comfort Chukka Boots

12 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

Tommy Hilfiger - Rosell. Color Black. On sale for $65.32. MSRP $79.95. 18% off.

Tommy Hilfiger Rosell

Tommy Hilfiger Rosell

Brand Name: Tommy Hilfiger
Product Name: Rosell
Gender: Men's
Color: Black
Price: $65.32MSRP: $79.95

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

Tommy Hilfiger - Rosell. Color Brown. On sale for $78.19. MSRP $79.95. 2% off.

Tommy Hilfiger Rosell

Tommy Hilfiger Rosell

Brand Name: Tommy Hilfiger
Product Name: Rosell
Gender: Men's
Color: Brown
Price: $78.19MSRP: $79.95

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

Roper - Gumsticker Romeo. Color Brown. Low Stock. On sale for $76.19. MSRP $126.99. 40% off.

Low Stock

Roper Gumsticker Romeo

Roper Gumsticker Romeo

Brand Name: Roper
Product Name: Gumsticker Romeo
Gender: Men's
Color: Brown
Price: $76.19MSRP: $126.99

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

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