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Boots on Sale $50 & Under

Shop Boots Deals

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Size 8.5 Chukka Boots

16 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

Eastland 1955 Edition - Hugo. Color Brown. Low Stock. On sale for $70.00. MSRP $100.00. 30% off.

Low Stock

Eastland 1955 Edition Hugo

Eastland 1955 Edition Hugo

Brand Name: Eastland 1955 Edition
Product Name: Hugo
Gender: Men's
Color: Brown
Price: $70MSRP: $100

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 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

Clarks - Desert Boots. Color Navy Suede. On sale for $120.00. MSRP $150.00. 20% off.

Clarks Desert Boots

Clarks Desert Boots

Brand Name: Clarks
Product Name: Desert Boots
Gender: Men's
Color: Navy Suede
Price: $120MSRP: $150

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

Born - Theo. Color Dark.Brown (Pyramid). 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: Dark.Brown (Pyramid)
Price: $71.50MSRP: $130

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

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 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

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

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

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

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