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Boots on Sale $50 & Under

Shop Boots Deals

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Chelsea Boots

24 items found

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Dr. Martens - 2976. Color Saddle Tan. On sale for $81.00. MSRP $180.00. 55% off. 3.4 out of 5 stars

Dr. Martens 2976

Dr. Martens 2976

Brand Name: Dr. Martens
Product Name: 2976
Gender: Men's
Color: Saddle Tan
Price: $81MSRP: $180

Martin Dingman - McKinley Wingtip Boot. Color Oak. Low Stock. On sale for $118.50. MSRP $395.00. 70% off.

Low Stock

Martin Dingman McKinley Wingtip Boot

Martin Dingman McKinley Wingtip Boot

Brand Name: Martin Dingman
Product Name: McKinley Wingtip Boot
Gender: Men's
Color: Oak
Price: $118.50MSRP: $395

Steve Madden - Montreaux. Color Tan. Low Stock. On sale for $58.50. MSRP $130.00. 55% off.

Low Stock

Steve Madden Montreaux

Steve Madden Montreaux

Brand Name: Steve Madden
Product Name: Montreaux
Gender: Men's
Color: Tan
Price: $58.50MSRP: $130

Calvin Klein - Donto. Color Medium Brown Leather. Low Stock. On sale for $45.60. MSRP $113.99. 60% off.

Low Stock

Calvin Klein Donto

Calvin Klein Donto

Brand Name: Calvin Klein
Product Name: Donto
Gender: Men's
Color: Medium Brown Leather
Price: $45.60MSRP: $113.99

Magnanni - Shaw. Color Rocia Taupe Suede. On sale for $445.50. MSRP $495.00. 10% off.

Magnanni Shaw

Magnanni Shaw

Brand Name: Magnanni
Product Name: Shaw
Gender: Men's
Color: Rocia Taupe Suede
Price: $445.50MSRP: $495

COACH - Carver Boot. Color Black. Low Stock. On sale for $248.81. MSRP $295.00. 16% off.

Low Stock

COACH Carver Boot

COACH Carver Boot

Brand Name: COACH
Product Name: Carver Boot
Gender: Men's
Color: Black
Price: $248.81MSRP: $295

Blake McKay - Redmond. Color Black. Low Stock. $165.00. 4.0 out of 5 stars

Low Stock

Blake McKay Redmond

Blake McKay Redmond

Brand Name: Blake McKay
Product Name: Redmond
Gender: Men's
Color: Black
Price: $165

Dr. Martens - 2976. Color Olive. On sale for $140.63. MSRP $180.00. 22% off. 3.4 out of 5 stars

Dr. Martens 2976

Dr. Martens 2976

Brand Name: Dr. Martens
Product Name: 2976
Gender: Men's
Color: Olive
Price: $140.63MSRP: $180

Eastland 1955 Edition - Herman. Color Peanut. Low Stock. On sale for $93.88. MSRP $135.00. 30% off.

Low Stock

Eastland 1955 Edition Herman

Eastland 1955 Edition Herman

Brand Name: Eastland 1955 Edition
Product Name: Herman
Gender: Men's
Color: Peanut
Price: $93.88MSRP: $135

Vince - Erik. Color Black. Low Stock. On sale for $180.00. MSRP $450.00. 60% off.

Low Stock

Vince Erik

Vince Erik

Brand Name: Vince
Product Name: Erik
Gender: Men's
Color: Black
Price: $180MSRP: $450

Ben Sherman - Birk Chelsea. Color Tan Leather. Low Stock. On sale for $65.25. MSRP $145.00. 55% off. 4.4 out of 5 stars

Low Stock

Ben Sherman Birk Chelsea

Ben Sherman Birk Chelsea

Brand Name: Ben Sherman
Product Name: Birk Chelsea
Gender: Men's
Color: Tan Leather
Price: $65.25MSRP: $145

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

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

Cole Haan - Originalgrand Cityspectre Chelsea Boots. Color Woodbury/Dark Natural/Silver Birch. On sale for $207.00. MSRP $230.00. 10% off.

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: $207MSRP: $230

Gordon Rush - Portland. Color Taupe Suede. Low Stock. On sale for $95.34. MSRP $158.90. 40% off. 2.5 out of 5 stars

Low Stock

Gordon Rush Portland

Gordon Rush Portland

Brand Name: Gordon Rush
Product Name: Portland
Gender: Men's
Color: Taupe Suede
Price: $95.34MSRP: $158.90

Stacy Adams - Bradley Chelsea Boot. Color Tan. On sale for $130.68. MSRP $160.00. 18% off. 5.0 out of 5 stars

Stacy Adams Bradley Chelsea Boot

Stacy Adams Bradley Chelsea Boot

Brand Name: Stacy Adams
Product Name: Bradley Chelsea Boot
Gender: Men's
Color: Tan
Price: $130.68MSRP: $160

Nunn Bush - Otis Plain Toe Chelsea Boot with KORE Walking Comfort Technology. Color Brown CH. On sale for $103.54. MSRP $115.00. 10% off. 4.2 out of 5 stars

Nunn Bush Otis Plain Toe Chelsea Boot with KORE Walking Comfort Technology

Nunn Bush Otis Plain Toe Chelsea Boot with KORE Walking Comfort Technology

Brand Name: Nunn Bush
Product Name: Otis Plain Toe Chelsea Boot with KORE Walking Comfort Technology
Gender: Men's
Color: Brown CH
Price: $103.54MSRP: $115

Eastland 1955 Edition - Daily Double. Color Dark Brown 2. Low Stock. On sale for $100.69. MSRP $125.00. 19% off. 3.4 out of 5 stars

Low Stock

Eastland 1955 Edition Daily Double

Eastland 1955 Edition Daily Double

Brand Name: Eastland 1955 Edition
Product Name: Daily Double
Gender: Men's
Color: Dark Brown 2
Price: $100.69MSRP: $125

Stacy Adams - Maury Cap Toe Chelsea Boot. Color Cognac. Low Stock. On sale for $92.58. MSRP $145.00. 36% off. 4.7 out of 5 stars

Low Stock

Stacy Adams Maury Cap Toe Chelsea Boot

Stacy Adams Maury Cap Toe Chelsea Boot

Brand Name: Stacy Adams
Product Name: Maury Cap Toe Chelsea Boot
Gender: Men's
Color: Cognac
Price: $92.58MSRP: $145

Stacy Adams - Maury Cap Toe Chelsea Boot. Color Black. Low Stock. On sale for $91.00. MSRP $145.00. 37% off. 4.7 out of 5 stars

Low Stock

Stacy Adams Maury Cap Toe Chelsea Boot

Stacy Adams Maury Cap Toe Chelsea Boot

Brand Name: Stacy Adams
Product Name: Maury Cap Toe Chelsea Boot
Gender: Men's
Color: Black
Price: $91MSRP: $145

Stacy Adams - Maury Cap Toe Chelsea Boot. Color Chocolate. On sale for $90.64. MSRP $145.00. 37% off. 4.7 out of 5 stars

Stacy Adams Maury Cap Toe Chelsea Boot

Stacy Adams Maury Cap Toe Chelsea Boot

Brand Name: Stacy Adams
Product Name: Maury Cap Toe Chelsea Boot
Gender: Men's
Color: Chocolate
Price: $90.64MSRP: $145

Eastland 1955 Edition - Daily Double. Color Brown Nubuck. Low Stock. On sale for $78.75. MSRP $125.00. 37% off. 3.4 out of 5 stars

Low Stock

Eastland 1955 Edition Daily Double

Eastland 1955 Edition Daily Double

Brand Name: Eastland 1955 Edition
Product Name: Daily Double
Gender: Men's
Color: Brown Nubuck
Price: $78.75MSRP: $125

Sperry - Mountain-Sider Chelsea. Color Brown. Low Stock. On sale for $71.50. MSRP $130.00. 45% off.

Low Stock

Sperry Mountain-Sider Chelsea

Sperry Mountain-Sider Chelsea

Brand Name: Sperry
Product Name: Mountain-Sider Chelsea
Gender: Men's
Color: Brown
Price: $71.50MSRP: $130

Marc Joseph New York - Austin. Color Cognac Washed Grainy. Low Stock. On sale for $126.75. MSRP $195.00. 35% off. 4.4 out of 5 stars

Low Stock

Marc Joseph New York Austin

Marc Joseph New York Austin

Brand Name: Marc Joseph New York
Product Name: Austin
Gender: Men's
Color: Cognac Washed Grainy
Price: $126.75MSRP: $195

Bogs - Classic Casual Chelsea II. Color Brown. Low Stock. On sale for $112.89. MSRP $150.00. 25% off. 4.5 out of 5 stars

Low Stock

Bogs Classic Casual Chelsea II

Bogs Classic Casual Chelsea II

Brand Name: Bogs
Product Name: Classic Casual Chelsea II
Gender: Men's
Color: Brown
Price: $112.89MSRP: $150