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Boots on Sale $50 & Under

Shop Boots Deals

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Ankle Black Chukka Boots

18 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

Tommy Hilfiger - Nyo. Color Black. On sale for $27.98. MSRP $79.95. 65% off.

Tommy Hilfiger Nyo

Tommy Hilfiger Nyo

Brand Name: Tommy Hilfiger
Product Name: Nyo
Gender: Men's
Color: Black
Price: $27.98MSRP: $79.95

Koolaburra by UGG - Advay. Color Black. On sale for $49.97. MSRP $84.99. 41% off. 3.6 out of 5 stars

Koolaburra by UGG Advay

Koolaburra by UGG Advay

Brand Name: Koolaburra by UGG
Product Name: Advay
Gender: Women's
Color: Black
Price: $49.97MSRP: $84.99

The North Face - Never Stop Exploring Chukka Suede. Color TNF Black/Asphalt Grey. 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: TNF Black/Asphalt Grey
Price: $93.75MSRP: $125

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 $65.29. MSRP $79.95. 18% off.

Tommy Hilfiger Rosell

Tommy Hilfiger Rosell

Brand Name: Tommy Hilfiger
Product Name: Rosell
Gender: Men's
Color: Black
Price: $65.29MSRP: $79.95

Comfortiva - Holland. Color Black. On sale for $77.97. MSRP $129.95. 40% off. 3.8 out of 5 stars

Comfortiva Holland

Comfortiva Holland

Brand Name: Comfortiva
Product Name: Holland
Gender: Women's
Color: Black
Price: $77.97MSRP: $129.95

Dr. Scholl's - Aurora. Color Charcoal Fabric. Low Stock. On sale for $83.82. MSRP $115.00. 27% off. 3.3 out of 5 stars

Low Stock

Dr. Scholl's Aurora

Dr. Scholl's Aurora

Brand Name: Dr. Scholl's
Product Name: Aurora
Gender: Women's
Color: Charcoal Fabric
Price: $83.82MSRP: $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 Black 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: Black Faux Leather
Price: $60MSRP: $120

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

Koolaburra by UGG - Advay (Little Kid/Big Kid). Color Black. On sale for $58.98. MSRP $64.99. 9% off. 4.3 out of 5 stars

Koolaburra by UGG Advay (Little Kid/Big Kid)

Koolaburra by UGG Advay (Little Kid/Big Kid)

Brand Name: Koolaburra by UGG
Product Name: Advay (Little Kid/Big Kid)
Color: Black
Price: $58.98MSRP: $64.99

Johnston & Murphy - Fullerton Chukka. Color Black. Low Stock. On sale for $83.25. MSRP $185.00. 55% off. 3.7 out of 5 stars

Low Stock

Johnston & Murphy Fullerton Chukka

Johnston & Murphy Fullerton Chukka

Brand Name: Johnston & Murphy
Product Name: Fullerton Chukka
Gender: Men's
Color: Black
Price: $83.25MSRP: $185

Cole Haan - Berkshire Lug Chukka Boots. Color Pavement Nubuck/Demitasse Water Resistant. Low Stock. $220.00. 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: Pavement Nubuck/Demitasse Water Resistant
Price: $220

Dolce Vita - Ronnie. Color Black Leather. Low Stock. On sale for $98.96. MSRP $220.00. 55% off. 3.5 out of 5 stars

Low Stock

Dolce Vita Ronnie

Dolce Vita Ronnie

Brand Name: Dolce Vita
Product Name: Ronnie
Gender: Women's
Color: Black Leather
Price: $98.96MSRP: $220

Easy Street - Ronnie. Color Black Suede. Low Stock. On sale for $23.99. MSRP $79.99. 70% off. 4.0 out of 5 stars

Low Stock

Easy Street Ronnie

Easy Street Ronnie

Brand Name: Easy Street
Product Name: Ronnie
Gender: Women's
Color: Black Suede
Price: $23.99MSRP: $79.99

Hey Dude - Wendy Peak Suede Fold Boot. Color Black. Low Stock. On sale for $80.99. MSRP $89.99. 10% off. 4.1 out of 5 stars

Low Stock

Hey Dude Wendy Peak Suede Fold Boot

Hey Dude Wendy Peak Suede Fold Boot

Brand Name: Hey Dude
Product Name: Wendy Peak Suede Fold Boot
Gender: Women's
Color: Black
Price: $80.99MSRP: $89.99

Steve Madden - Harken - Extended Sizes. Color Black. Low Stock. On sale for $69.99. MSRP $99.99. 30% 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: $69.99MSRP: $99.99