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Boots on Sale $50 & Under

Shop Boots Deals

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Men's Chelsea Boots

35 items found

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Deer Stags - Argos. Color Black/Blue. On sale for $59.30. MSRP $100.00. 41% off. 3.7 out of 5 stars

Deer Stags Argos

Deer Stags Argos

Brand Name: Deer Stags
Product Name: Argos
Gender: Men's
Color: Black/Blue
Price: $59.30MSRP: $100

Sperry - Clifton Boot MM. Color Black. Low Stock. On sale for $55.00. MSRP $110.00. 50% off. 3.0 out of 5 stars

Low Stock

Sperry Clifton Boot MM

Sperry Clifton Boot MM

Brand Name: Sperry
Product Name: Clifton Boot MM
Gender: Men's
Color: Black
Price: $55MSRP: $110

Kenneth Cole - Tully Chelsea Boots. Color Black Leather. On sale for $129.50. MSRP $184.95. 30% off. 5.0 out of 5 stars

Kenneth Cole Tully Chelsea Boots

Kenneth Cole Tully Chelsea Boots

Brand Name: Kenneth Cole
Product Name: Tully Chelsea Boots
Gender: Men's
Color: Black Leather
Price: $129.50MSRP: $184.95

Kenneth Cole - Tully Chelsea Boots. Color Medium Brown Leather. On sale for $126.24. MSRP $184.95. 32% off. 5.0 out of 5 stars

Kenneth Cole Tully Chelsea Boots

Kenneth Cole Tully Chelsea Boots

Brand Name: Kenneth Cole
Product Name: Tully Chelsea Boots
Gender: Men's
Color: Medium Brown Leather
Price: $126.24MSRP: $184.95

Marc Joseph New York - Austin. Color Truffle Washed Grainy. Low Stock. On sale for $58.50. MSRP $195.00. 70% off. 4.1 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: Truffle Washed Grainy
Price: $58.50MSRP: $195

Steve Madden - Noah. Color Taupe Suede. Low Stock. On sale for $43.99. MSRP $79.99. 45% off. 4.3 out of 5 stars

Low Stock

Steve Madden Noah

Brand Name: Steve Madden
Product Name: Noah
Gender: Men's
Color: Taupe Suede
Price: $43.99MSRP: $79.99

Merrell - Moab Adventure 3 Chelsea Wp. Color Black. On sale for $126.99. MSRP $170.00. 25% off. 2.9 out of 5 stars

Merrell Moab Adventure 3 Chelsea Wp

Merrell Moab Adventure 3 Chelsea Wp

Brand Name: Merrell
Product Name: Moab Adventure 3 Chelsea Wp
Gender: Men's
Color: Black
Price: $126.99MSRP: $170

Vans - Mte™ Standard Mid Chelsea Waterproof. Color Faded Black. Low Stock. On sale for $60.00. MSRP $150.00. 60% off. 3.2 out of 5 stars

Low Stock

Vans Mte™ Standard Mid Chelsea Waterproof

Vans Mte™ Standard Mid Chelsea Waterproof

Brand Name: Vans
Product Name: Mte™ Standard Mid Chelsea Waterproof
Gender: Unisex
Color: Faded Black
Price: $60MSRP: $150

Globe - Dover II Vibram. Color Brown Crazyhorse. Low Stock. On sale for $89.97. MSRP $199.95. 55% off.

Low Stock

Globe Dover II Vibram

Globe Dover II Vibram

Brand Name: Globe
Product Name: Dover II Vibram
Gender: Men's
Color: Brown Crazyhorse
Price: $89.97MSRP: $199.95

SOREL - Slabtown 62'™ Chelsea Waterproof. Color Tobacco/Black. Low Stock. $170.00. 4.0 out of 5 stars

Low Stock

SOREL Slabtown 62'™ Chelsea Waterproof

SOREL Slabtown 62'™ Chelsea Waterproof

Brand Name: SOREL
Product Name: Slabtown 62'™ Chelsea Waterproof
Gender: Men's
Color: Tobacco/Black
Price: $170

SOREL - Cyprus Chelsea Waterproof. Color Khaki Ii/Jet. On sale for $62.50. MSRP $125.00. 50% off. 1.0 out of 5 stars

SOREL Cyprus Chelsea Waterproof

SOREL Cyprus Chelsea Waterproof

Brand Name: SOREL
Product Name: Cyprus Chelsea Waterproof
Gender: Men's
Color: Khaki Ii/Jet
Price: $62.50MSRP: $125

SOREL - Cyprus Chelsea Waterproof. Color Velvet Tan/Gum 10. $125.00. 1.0 out of 5 stars

SOREL Cyprus Chelsea Waterproof

SOREL Cyprus Chelsea Waterproof

Brand Name: SOREL
Product Name: Cyprus Chelsea Waterproof
Gender: Men's
Color: Velvet Tan/Gum 10
Price: $125

SOREL - Cyprus Chelsea Waterproof. Color Tobacco/Blackened Brown. $125.00. 1.0 out of 5 stars

SOREL Cyprus Chelsea Waterproof

SOREL Cyprus Chelsea Waterproof

Brand Name: SOREL
Product Name: Cyprus Chelsea Waterproof
Gender: Men's
Color: Tobacco/Blackened Brown
Price: $125

Deer Stags - Brayden. Color Brown. On sale for $77.09. MSRP $100.00. 23% 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: $77.09MSRP: $100

Eastland 1955 Edition - Herman. Color Black. Low Stock. On sale for $59.97. MSRP $135.00. 56% off.

Low Stock

Eastland 1955 Edition Herman

Eastland 1955 Edition Herman

Brand Name: Eastland 1955 Edition
Product Name: Herman
Gender: Men's
Color: Black
Price: $59.97MSRP: $135

Eastland 1955 Edition - Herman. Color Brown. Low Stock. On sale for $67.50. MSRP $135.00. 50% off.

Low Stock

Eastland 1955 Edition Herman

Eastland 1955 Edition Herman

Brand Name: Eastland 1955 Edition
Product Name: Herman
Gender: Men's
Color: Brown
Price: $67.50MSRP: $135

Kenneth Cole - Hulard. Color Medium Brown. On sale for $87.78. MSRP $128.95. 32% off.

Kenneth Cole Hulard

Kenneth Cole Hulard

Brand Name: Kenneth Cole
Product Name: Hulard
Gender: Men's
Color: Medium Brown
Price: $87.78MSRP: $128.95

Cole Haan - Newmark Grand Chelsea Boots. Color Black Waterproof/Black/Black. Low Stock. On sale for $85.00. MSRP $170.00. 50% off. 5.0 out of 5 stars

Low Stock

Cole Haan Newmark Grand Chelsea Boots

Cole Haan Newmark Grand Chelsea Boots

Brand Name: Cole Haan
Product Name: Newmark Grand Chelsea Boots
Gender: Men's
Color: Black Waterproof/Black/Black
Price: $85MSRP: $170

Cole Haan - American Classics Chelsea Boots. Color Madeira Waterproof/Dark Java/Dark Java. Low Stock. On sale for $100.00. MSRP $200.00. 50% off. 3.0 out of 5 stars

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: Madeira Waterproof/Dark Java/Dark Java
Price: $100MSRP: $200

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

Columbia - Landroamer™ Scout NB. Color Curry/Poppy Red. Low Stock. On sale for $90.00. MSRP $100.00. 10% off. 3.7 out of 5 stars

Low Stock

Columbia Landroamer™ Scout NB

Columbia Landroamer™ Scout NB

Brand Name: Columbia
Product Name: Landroamer™ Scout NB
Gender: Men's
Color: Curry/Poppy Red
Price: $90MSRP: $100

Kenneth Cole - Frank. Color Black Leather. On sale for $129.50. MSRP $184.95. 30% off.

Kenneth Cole Frank

Kenneth Cole Frank

Brand Name: Kenneth Cole
Product Name: Frank
Gender: Men's
Color: Black Leather
Price: $129.50MSRP: $184.95

Kenneth Cole - Frank. Color Light Brown Leather. On sale for $129.50. MSRP $184.95. 30% off.

Kenneth Cole Frank

Kenneth Cole Frank

Brand Name: Kenneth Cole
Product Name: Frank
Gender: Men's
Color: Light Brown Leather
Price: $129.50MSRP: $184.95

Stacy Adams - Gabriel Chelsea Boot. Color Mushroom. Low Stock. On sale for $91.00. MSRP $130.00. 30% off. 4.2 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: $91MSRP: $130

Stacy Adams - Finney Cap Toe Chelsea Boot. Color Navy Multi. Low Stock. On sale for $48.00. MSRP $160.00. 70% off. 4.7 out of 5 stars

Low Stock

Stacy Adams Finney Cap Toe Chelsea Boot

Stacy Adams Finney Cap Toe Chelsea Boot

Brand Name: Stacy Adams
Product Name: Finney Cap Toe Chelsea Boot
Gender: Men's
Color: Navy Multi
Price: $48MSRP: $160

Kenneth Cole - Raymond. Color Black Leather. On sale for $138.71. MSRP $184.95. 25% off.

Kenneth Cole Raymond

Kenneth Cole Raymond

Brand Name: Kenneth Cole
Product Name: Raymond
Gender: Men's
Color: Black Leather
Price: $138.71MSRP: $184.95

Kenneth Cole - Raymond. Color Mocha Multi. On sale for $129.46. MSRP $184.95. 30% off.

Kenneth Cole Raymond

Kenneth Cole Raymond

Brand Name: Kenneth Cole
Product Name: Raymond
Gender: Men's
Color: Mocha Multi
Price: $129.46MSRP: $184.95

Stacy Adams - Maury Cap Toe Chelsea Boot. Color Cognac. Low Stock. On sale for $105.25. MSRP $145.00. 27% 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: $105.25MSRP: $145

Stacy Adams - Maury Cap Toe Chelsea Boot. Color Chocolate. Low Stock. On sale for $83.29. MSRP $145.00. 43% 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: Chocolate
Price: $83.29MSRP: $145

Polo Ralph Lauren - Asher Leather Chelsea Boots. Color Black. Low Stock. On sale for $184.73. MSRP $198.00. 7% off. 3.0 out of 5 stars

Low Stock

Polo Ralph Lauren Asher Leather Chelsea Boots

Polo Ralph Lauren Asher Leather Chelsea Boots

Brand Name: Polo Ralph Lauren
Product Name: Asher Leather Chelsea Boots
Gender: Men's
Color: Black
Price: $184.73MSRP: $198

Vans - Mte™ Standard Mid Chelsea Waterproof. Color Bay Leaf. On sale for $75.00. MSRP $150.00. 50% off. 3.2 out of 5 stars

Vans Mte™ Standard Mid Chelsea Waterproof

Vans Mte™ Standard Mid Chelsea Waterproof

Brand Name: Vans
Product Name: Mte™ Standard Mid Chelsea Waterproof
Gender: Unisex
Color: Bay Leaf
Price: $75MSRP: $150

Globe - Dover II Trek. Color Wheat/Gum/Summit. On sale for $87.46. MSRP $124.95. 30% off.

Globe Dover II Trek

Globe Dover II Trek

Brand Name: Globe
Product Name: Dover II Trek
Gender: Men's
Color: Wheat/Gum/Summit
Price: $87.46MSRP: $124.95

SOREL - Slabtown 62' Chelsea Waterproof. Color Canoe/Black. Low Stock. On sale for $85.00. MSRP $170.00. 50% off.

Low Stock

SOREL Slabtown 62' Chelsea Waterproof

SOREL Slabtown 62' Chelsea Waterproof

Brand Name: SOREL
Product Name: Slabtown 62' Chelsea Waterproof
Gender: Men's
Color: Canoe/Black
Price: $85MSRP: $170

Vans - Mte™ Standard Mid Chelsea Waterproof. Color 30th Anniversary Gray Olive. Low Stock. On sale for $60.00. MSRP $150.00. 60% off. 3.2 out of 5 stars

Low Stock

Vans Mte™ Standard Mid Chelsea Waterproof

Vans Mte™ Standard Mid Chelsea Waterproof

Brand Name: Vans
Product Name: Mte™ Standard Mid Chelsea Waterproof
Gender: Unisex
Color: 30th Anniversary Gray Olive
Price: $60MSRP: $150

Vans - Mte™ Standard Mid Chelsea Waterproof. Color Oatmeal/Brown. On sale for $82.50. MSRP $150.00. 45% off. 3.2 out of 5 stars

Vans Mte™ Standard Mid Chelsea Waterproof

Vans Mte™ Standard Mid Chelsea Waterproof

Brand Name: Vans
Product Name: Mte™ Standard Mid Chelsea Waterproof
Gender: Unisex
Color: Oatmeal/Brown
Price: $82.50MSRP: $150