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Boots on Sale $50 & Under

Shop Boots Deals

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Medium Size Ankle Leather Casual Products

124 items found

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Johnston & Murphy - Dudley Chukka. Color Brown Waxed English Suede. Low Stock. On sale for $82.50. MSRP $275.00. 70% off.

Low Stock

Johnston & Murphy Dudley Chukka

Johnston & Murphy Dudley Chukka

Brand Name: Johnston & Murphy
Product Name: Dudley Chukka
Gender: Men's
Color: Brown Waxed English Suede
Price: $82.50MSRP: $275

Johnston & Murphy - Bolivar Plain Toe Boots. Color Snuff Italian Suede. Low Stock. On sale for $114.00. MSRP $285.00. 60% off.

Low Stock

Johnston & Murphy Bolivar Plain Toe Boots

Johnston & Murphy Bolivar Plain Toe Boots

Brand Name: Johnston & Murphy
Product Name: Bolivar Plain Toe Boots
Gender: Men's
Color: Snuff Italian Suede
Price: $114MSRP: $285

Johnston & Murphy - Hartley Wingtip Boot. Color Snuff Italian Suede. Low Stock. On sale for $130.00. MSRP $325.00. 60% off.

Low Stock

Johnston & Murphy Hartley Wingtip Boot

Johnston & Murphy Hartley Wingtip Boot

Brand Name: Johnston & Murphy
Product Name: Hartley Wingtip Boot
Gender: Men's
Color: Snuff Italian Suede
Price: $130MSRP: $325

Johnston & Murphy - Dudley Lug Plain Toe Boot. Color Brown. Low Stock. On sale for $199.50. MSRP $285.00. 30% off.

Low Stock

Johnston & Murphy Dudley Lug Plain Toe Boot

Johnston & Murphy Dudley Lug Plain Toe Boot

Brand Name: Johnston & Murphy
Product Name: Dudley Lug Plain Toe Boot
Gender: Men's
Color: Brown
Price: $199.50MSRP: $285

Dansko - Stephanie. Color Morel Waterproof Suede. Low Stock. On sale for $65.64. MSRP $189.99. 65% off. 3.4 out of 5 stars

Low Stock

Dansko Stephanie

Dansko Stephanie

Brand Name: Dansko
Product Name: Stephanie
Gender: Women's
Color: Morel Waterproof Suede
Price: $65.64MSRP: $189.99

Cole Haan - Muir Moc Tall Boots. Color Bloodstone/Raven Wp. On sale for $169.51. MSRP $208.00. 19% off.

Cole Haan Muir Moc Tall Boots

Cole Haan Muir Moc Tall Boots

Brand Name: Cole Haan
Product Name: Muir Moc Tall Boots
Gender: Men's
Color: Bloodstone/Raven Wp
Price: $169.51MSRP: $208

Deer Stags - Brayden. Color Brown. On sale for $70.00. MSRP $100.00. 30% off. 3.3 out of 5 stars

Deer Stags Brayden

Deer Stags Brayden

Brand Name: Deer Stags
Product Name: Brayden
Gender: Men's
Color: Brown
Price: $70MSRP: $100

Palladium - Pampa Sport Cuff WPN. Color Black. Low Stock. On sale for $41.98. MSRP $139.95. 70% off. 4.3 out of 5 stars

Low Stock

Palladium Pampa Sport Cuff WPN

Palladium Pampa Sport Cuff WPN

Brand Name: Palladium
Product Name: Pampa Sport Cuff WPN
Gender: Unisex
Color: Black
Price: $41.98MSRP: $139.95

Cole Haan - American Classics Chelsea Boots. Color Black Waterproof/Black/Black. Low Stock. On sale for $170.00. MSRP $200.00. 15% off.

Low Stock

Cole Haan American Classics Chelsea Boots

Cole Haan American Classics Chelsea Boots

Brand Name: Cole Haan
Product Name: American Classics Chelsea Boots
Gender: Men's
Color: Black Waterproof/Black/Black
Price: $170MSRP: $200

Cole Haan - Originalgrand Cityspectre Chelsea Boots. Color Black/Black. Low Stock. On sale for $207.00. MSRP $230.00. 10% off.

Low Stock

Cole Haan Originalgrand Cityspectre Chelsea Boots

Cole Haan Originalgrand Cityspectre Chelsea Boots

Brand Name: Cole Haan
Product Name: Originalgrand Cityspectre Chelsea Boots
Gender: Men's
Color: Black/Black
Price: $207MSRP: $230

Steve Madden - Jotter. Color Dark Tan. Low Stock. On sale for $100.00. MSRP $109.99. 9% off. 4.4 out of 5 stars

Low Stock

Steve Madden Jotter

Steve Madden Jotter

Brand Name: Steve Madden
Product Name: Jotter
Gender: Men's
Color: Dark Tan
Price: $100MSRP: $109.99

Dunham - Cloud Plus Mid II Waterproof Boot. Color Brown Leather. Low Stock. On sale for $143.95. MSRP $179.95. 20% off. 4.3 out of 5 stars

Low Stock

Dunham Cloud Plus Mid II Waterproof Boot

Dunham Cloud Plus Mid II Waterproof Boot

Brand Name: Dunham
Product Name: Cloud Plus Mid II Waterproof Boot
Gender: Men's
Color: Brown Leather
Price: $143.95MSRP: $179.95

Dansko - Stephanie. Color Black Waterproof Suede. Low Stock. On sale for $94.07. MSRP $189.99. 50% off. 3.4 out of 5 stars

Low Stock

Dansko Stephanie

Dansko Stephanie

Brand Name: Dansko
Product Name: Stephanie
Gender: Women's
Color: Black Waterproof Suede
Price: $94.07MSRP: $189.99

Dr. Martens - 1460 Crazy Horse Leather Boots. Color Brown Crazy Horse. Low Stock. $169.99. 4.3 out of 5 stars

Low Stock

Dr. Martens 1460 Crazy Horse Leather Boots

Dr. Martens 1460 Crazy Horse Leather Boots

Brand Name: Dr. Martens
Product Name: 1460 Crazy Horse Leather Boots
Gender: Unisex
Color: Brown Crazy Horse
Price: $169.99

Deer Stags - Brayden. Color Black. On sale for $70.00. MSRP $100.00. 30% off. 3.3 out of 5 stars

Deer Stags Brayden

Deer Stags Brayden

Brand Name: Deer Stags
Product Name: Brayden
Gender: Men's
Color: Black
Price: $70MSRP: $100

Cole Haan - Morse Grand Chukka Boots. Color Morel Suede/Ivory. Low Stock. On sale for $133.20. MSRP $148.00. 10% off.

Low Stock

Cole Haan Morse Grand Chukka Boots

Cole Haan Morse Grand Chukka Boots

Brand Name: Cole Haan
Product Name: Morse Grand Chukka Boots
Gender: Men's
Color: Morel Suede/Ivory
Price: $133.20MSRP: $148

Bogs - Classic Casual Rain. Color Black. Low Stock. On sale for $106.12. MSRP $135.00. 21% off. 4.4 out of 5 stars

Low Stock

Bogs Classic Casual Rain

Bogs Classic Casual Rain

Brand Name: Bogs
Product Name: Classic Casual Rain
Gender: Men's
Color: Black
Price: $106.12MSRP: $135

Cole Haan - Originalgrand Cityspectre Chelsea Boots. Color Woodbury/Dark Natural/Silver Birch. Low Stock. On sale for $115.00. MSRP $230.00. 50% off.

Low Stock

Cole Haan Originalgrand Cityspectre Chelsea Boots

Cole Haan Originalgrand Cityspectre Chelsea Boots

Brand Name: Cole Haan
Product Name: Originalgrand Cityspectre Chelsea Boots
Gender: Men's
Color: Woodbury/Dark Natural/Silver Birch
Price: $115MSRP: $230

Frye - Tyler Flex Chelsea. Color Black. On sale for $201.00. MSRP $268.00. 25% off. 3.6 out of 5 stars

Frye Tyler Flex Chelsea

Frye Tyler Flex Chelsea

Brand Name: Frye
Product Name: Tyler Flex Chelsea
Gender: Men's
Color: Black
Price: $201MSRP: $268

Dr. Martens - 1460. Color Nickel Grey. On sale for $110.50. MSRP $170.00. 35% off.

Dr. Martens 1460

Dr. Martens 1460

Brand Name: Dr. Martens
Product Name: 1460
Gender: Unisex
Color: Nickel Grey
Price: $110.50MSRP: $170

Sperry - Stringer. Color Tan. On sale for $117.00. MSRP $130.00. 10% off.

Sperry Stringer

Sperry Stringer

Brand Name: Sperry
Product Name: Stringer
Gender: Men's
Color: Tan
Price: $117MSRP: $130

Sperry - Tour Mid Moc. Color Tan. Low Stock. On sale for $126.00. MSRP $140.00. 10% off.

Low Stock

Sperry Tour Mid Moc

Sperry Tour Mid Moc

Brand Name: Sperry
Product Name: Tour Mid Moc
Gender: Men's
Color: Tan
Price: $126MSRP: $140

Sperry - Norfolk Boots. Color Brown. Low Stock. On sale for $90.00. MSRP $100.00. 10% off. 1.0 out of 5 stars

Low Stock

Sperry Norfolk Boots

Sperry Norfolk Boots

Brand Name: Sperry
Product Name: Norfolk Boots
Gender: Men's
Color: Brown
Price: $90MSRP: $100

Sperry - Tour Mid Moc. Color Dark Brown. On sale for $126.00. MSRP $140.00. 10% off.

Sperry Tour Mid Moc

Sperry Tour Mid Moc

Brand Name: Sperry
Product Name: Tour Mid Moc
Gender: Men's
Color: Dark Brown
Price: $126MSRP: $140

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