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Boots on Sale $50 & Under

Shop Boots Deals

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Chelsea Boots

25 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

Tommy Hilfiger - Risten. Color Black. Low Stock. On sale for $35.97. MSRP $79.95. 55% off.

Low Stock

Tommy Hilfiger Risten

Tommy Hilfiger Risten

Brand Name: Tommy Hilfiger
Product Name: Risten
Gender: Men's
Color: Black
Price: $35.97MSRP: $79.95

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

Steve Madden - Merrnie. Color Tan. On sale for $71.99. MSRP $79.99. 10% off.

Steve Madden Merrnie

Steve Madden Merrnie

Brand Name: Steve Madden
Product Name: Merrnie
Gender: Men's
Color: Tan
Price: $71.99MSRP: $79.99

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 - 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

Sperry - Mountain-Sider Chelsea. Color Brown. Low Stock. On sale for $104.00. MSRP $130.00. 20% 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: $104MSRP: $130

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

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

Kenneth Cole - Hulard. Color Black. On sale for $90.30. MSRP $128.95. 30% off.

Kenneth Cole Hulard

Kenneth Cole Hulard

Brand Name: Kenneth Cole
Product Name: Hulard
Gender: Men's
Color: Black
Price: $90.30MSRP: $128.95

Kenneth Cole - Hulard. Color Medium Brown. On sale for $98.25. MSRP $128.95. 24% off.

Kenneth Cole Hulard

Kenneth Cole Hulard

Brand Name: Kenneth Cole
Product Name: Hulard
Gender: Men's
Color: Medium Brown
Price: $98.25MSRP: $128.95

Tommy Hilfiger - Risten. Color Brown. Low Stock. On sale for $71.95. MSRP $79.95. 10% off.

Low Stock

Tommy Hilfiger Risten

Tommy Hilfiger Risten

Brand Name: Tommy Hilfiger
Product Name: Risten
Gender: Men's
Color: Brown
Price: $71.95MSRP: $79.95

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

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

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

Eastland 1955 Edition - Cyrus. Color Brown. Low Stock. On sale for $67.50. MSRP $90.00. 25% off. 1.0 out of 5 stars

Low Stock

Eastland 1955 Edition Cyrus

Eastland 1955 Edition Cyrus

Brand Name: Eastland 1955 Edition
Product Name: Cyrus
Gender: Men's
Color: Brown
Price: $67.50MSRP: $90

Eastland 1955 Edition - Cyrus. Color Nutmeg. Low Stock. On sale for $40.50. MSRP $90.00. 55% off. 1.0 out of 5 stars

Low Stock

Eastland 1955 Edition Cyrus

Eastland 1955 Edition Cyrus

Brand Name: Eastland 1955 Edition
Product Name: Cyrus
Gender: Men's
Color: Nutmeg
Price: $40.50MSRP: $90

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

SOREL - Carson™ Chelsea Waterproof. Color Brown. On sale for $139.50. MSRP $155.00. 10% off. 1.0 out of 5 stars

SOREL Carson™ Chelsea Waterproof

SOREL Carson™ Chelsea Waterproof

Brand Name: SOREL
Product Name: Carson™ Chelsea Waterproof
Gender: Men's
Color: Brown
Price: $139.50MSRP: $155

Stacy Adams - Gabriel Chelsea Boot. Color Chocolate Suede. Low Stock. On sale for $89.91. MSRP $130.00. 31% off. 4.6 out of 5 stars

Low Stock

Stacy Adams Gabriel Chelsea Boot

Stacy Adams Gabriel Chelsea Boot

Brand Name: Stacy Adams
Product Name: Gabriel Chelsea Boot
Gender: Men's
Color: Chocolate Suede
Price: $89.91MSRP: $130

Stacy Adams - Gabriel Chelsea Boot. Color Mushroom. Low Stock. On sale for $88.02. MSRP $130.00. 32% off. 4.6 out of 5 stars

Low Stock

Stacy Adams Gabriel Chelsea Boot

Stacy Adams Gabriel Chelsea Boot

Brand Name: Stacy Adams
Product Name: Gabriel Chelsea Boot
Gender: Men's
Color: Mushroom
Price: $88.02MSRP: $130

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

Stacy Adams - Bradley Chelsea Boot. Color Tan. On sale for $136.00. MSRP $160.00. 15% 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: $136MSRP: $160