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Boots on Sale $50 & Under

Shop Boots Deals

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Medium Size Elastic Leather Boots

21 items found

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Dr. Martens - Rilla. Color Savannah Tan. On sale for $71.50. MSRP $130.00. 45% off.

Dr. Martens Rilla

Dr. Martens Rilla

Brand Name: Dr. Martens
Product Name: Rilla
Gender: Unisex
Color: Savannah Tan
Price: $71.50MSRP: $130

Globe - Dover II Vibram. Color Brown Crazyhorse. Low Stock. On sale for $99.97. MSRP $199.95. 50% 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: $99.97MSRP: $199.95

Nisolo - All-Weather Chelsea Boot. Color Dark Tobacco. On sale for $104.00. MSRP $260.00. 60% off. 1.5 out of 5 stars

Nisolo All-Weather Chelsea Boot

Nisolo All-Weather Chelsea Boot

Brand Name: Nisolo
Product Name: All-Weather Chelsea Boot
Gender: Men's
Color: Dark Tobacco
Price: $104MSRP: $260

Dr. Martens - 2976. Color Saddle Tan. Low Stock. On sale for $117.00. MSRP $180.00. 35% off. 3.7 out of 5 stars

Low Stock

Dr. Martens 2976

Dr. Martens 2976

Brand Name: Dr. Martens
Product Name: 2976
Gender: Men's
Color: Saddle Tan
Price: $117MSRP: $180

Cole Haan - American Classics Chelsea Boots. Color Madeira Waterproof/Dark Java/Dark Java. On sale for $151.68. MSRP $200.00. 24% off.

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: $151.68MSRP: $200

Cole Haan - American Classics Chelsea Boots. Color Morel Nubuck Waterproof/Black. On sale for $169.49. MSRP $200.00. 15% off.

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: Morel Nubuck Waterproof/Black
Price: $169.49MSRP: $200

Columbia - Landroamer™ Scout. Color Black/Dark Grey. Low Stock. On sale for $82.90. MSRP $100.00. 17% off. 4.2 out of 5 stars

Low Stock

Columbia Landroamer™ Scout

Columbia Landroamer™ Scout

Brand Name: Columbia
Product Name: Landroamer™ Scout
Gender: Men's
Color: Black/Dark Grey
Price: $82.90MSRP: $100

Deer Stags - Argos. Color Black/Blue. On sale for $51.00. MSRP $100.00. 49% 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: $51MSRP: $100

Dr. Martens - Rilla. Color Black. On sale for $108.57. MSRP $130.00. 16% off.

Dr. Martens Rilla

Dr. Martens Rilla

Brand Name: Dr. Martens
Product Name: Rilla
Gender: Unisex
Color: Black
Price: $108.57MSRP: $130

Steve Madden - Hatford. Color Black. On sale for $81.93. MSRP $100.00. 18% off.

Steve Madden Hatford

Steve Madden Hatford

Brand Name: Steve Madden
Product Name: Hatford
Gender: Men's
Color: Black
Price: $81.93MSRP: $100

Columbia - Landroamer Scout Nubuck. Color Black/Canyon Sun. Low Stock. On sale for $87.05. MSRP $100.00. 13% off. 2.3 out of 5 stars

Low Stock

Columbia Landroamer Scout Nubuck

Columbia Landroamer Scout Nubuck

Brand Name: Columbia
Product Name: Landroamer Scout Nubuck
Gender: Men's
Color: Black/Canyon Sun
Price: $87.05MSRP: $100

Nunn Bush - Otis Plain Toe Chelsea Boot with KORE Walking Comfort Technology. Color Brown CH. On sale for $102.69. MSRP $115.00. 11% 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: $102.69MSRP: $115

Johnston & Murphy - Calder Chelsea Boots. Color Black Tumbled Full Grain. Low Stock. On sale for $148.50. MSRP $179.00. 17% off. 5.0 out of 5 stars

Low Stock

Johnston & Murphy Calder Chelsea Boots

Johnston & Murphy Calder Chelsea Boots

Brand Name: Johnston & Murphy
Product Name: Calder Chelsea Boots
Gender: Men's
Color: Black Tumbled Full Grain
Price: $148.50MSRP: $179

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

Stacy Adams - Maury Cap Toe Chelsea Boot. Color Cognac. Low Stock. On sale for $106.98. MSRP $145.00. 26% 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: $106.98MSRP: $145

Stacy Adams - Maury Cap Toe Chelsea Boot. Color Chocolate. Low Stock. On sale for $79.75. MSRP $145.00. 45% 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: $79.75MSRP: $145

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

Deer Stags - Brayden. Color Brown. On sale for $55.25. MSRP $100.00. 45% 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: $55.25MSRP: $100

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

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

Johnston & Murphy - XC4 Stanton 2.0 Chelsea. Color Black Waterproof Full Grain. Low Stock. On sale for $139.30. MSRP $199.00. 30% off. 1.0 out of 5 stars

Low Stock

Johnston & Murphy XC4 Stanton 2.0 Chelsea

Johnston & Murphy XC4 Stanton 2.0 Chelsea

Brand Name: Johnston & Murphy
Product Name: XC4 Stanton 2.0 Chelsea
Gender: Men's
Color: Black Waterproof Full Grain
Price: $139.30MSRP: $199