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Sneakers on Sale $50 & Under

Shop Sneaker Deals

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Men's Ankle Leather On Sale Products

41 items found

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Steve Madden - Hatford. Color Black. Low Stock. On sale for $30.00. MSRP $100.00. 70% off.

Low Stock

Steve Madden Hatford

Steve Madden Hatford

Brand Name: Steve Madden
Product Name: Hatford
Gender: Men's
Color: Black
Price: $30MSRP: $100

Vans - U Mte™ Snow-kicker Gore-tex®. Color Bay Leaf. Low Stock. On sale for $60.00. MSRP $300.00. 80% off. 5.0 out of 5 stars

Low Stock

Vans U Mte™ Snow-kicker Gore-tex®

Vans U Mte™ Snow-kicker Gore-tex®

Brand Name: Vans
Product Name: U Mte™ Snow-kicker Gore-tex®
Gender: Unisex
Color: Bay Leaf
Price: $60MSRP: $300

Dr. Martens - 939. Color Savannah Tan. On sale for $96.00. MSRP $160.00. 40% off. 3.7 out of 5 stars

Dr. Martens 939

Dr. Martens 939

Brand Name: Dr. Martens
Product Name: 939
Gender: Unisex
Color: Savannah Tan
Price: $96MSRP: $160

Eastland 1955 Edition - Allagash Standard. Color Peanut. Low Stock. On sale for $43.50. MSRP $145.00. 70% off. 5.0 out of 5 stars

Low Stock

Eastland 1955 Edition Allagash Standard

Eastland 1955 Edition Allagash Standard

Brand Name: Eastland 1955 Edition
Product Name: Allagash Standard
Gender: Men's
Color: Peanut
Price: $43.50MSRP: $145

Ariat - Saylor Shrimp H2o. Color White. On sale for $59.97. MSRP $119.95. 50% off.

Ariat Saylor Shrimp H2o

Ariat Saylor Shrimp H2o

Brand Name: Ariat
Product Name: Saylor Shrimp H2o
Gender: Men's
Color: White
Price: $59.97MSRP: $119.95

Dr. Martens - 2976 Lo Chelsea. Color Kelp Brown. On sale for $80.00. MSRP $160.00. 50% off. 4.0 out of 5 stars

Dr. Martens 2976 Lo Chelsea

Dr. Martens 2976 Lo Chelsea

Brand Name: Dr. Martens
Product Name: 2976 Lo Chelsea
Gender: Unisex
Color: Kelp Brown
Price: $80MSRP: $160

Dr. Martens - 2976 Quad Chelsea. Color Cherry Red. On sale for $126.00. MSRP $210.00. 40% off. 4.5 out of 5 stars

Dr. Martens 2976 Quad Chelsea

Dr. Martens 2976 Quad Chelsea

Brand Name: Dr. Martens
Product Name: 2976 Quad Chelsea
Gender: Unisex
Color: Cherry Red
Price: $126MSRP: $210

Dr. Martens - 1460 Inferno. Color Cherry Red. Low Stock. On sale for $119.00. MSRP $170.00. 30% off. 2.8 out of 5 stars

Low Stock

Dr. Martens 1460 Inferno

Dr. Martens 1460 Inferno

Brand Name: Dr. Martens
Product Name: 1460 Inferno
Gender: Unisex
Color: Cherry Red
Price: $119MSRP: $170

Dr. Martens - 2976 Harness. Color Black. On sale for $126.00. MSRP $180.00. 30% off. 4.0 out of 5 stars

Dr. Martens 2976 Harness

Dr. Martens 2976 Harness

Brand Name: Dr. Martens
Product Name: 2976 Harness
Gender: Unisex
Color: Black
Price: $126MSRP: $180

Steve Madden - Tabriz. Color Brown. Low Stock. On sale for $42.00. MSRP $140.00. 70% off. 2.0 out of 5 stars

Low Stock

Steve Madden Tabriz

Steve Madden Tabriz

Brand Name: Steve Madden
Product Name: Tabriz
Gender: Men's
Color: Brown
Price: $42MSRP: $140

SOREL - Slabtown 62'™ Six Waterproof. Color Velvet Tan/Tawny Buff. Low Stock. On sale for $131.25. MSRP $175.00. 25% off. 4.0 out of 5 stars

Low Stock

SOREL Slabtown 62'™ Six Waterproof

SOREL Slabtown 62'™ Six Waterproof

Brand Name: SOREL
Product Name: Slabtown 62'™ Six Waterproof
Gender: Men's
Color: Velvet Tan/Tawny Buff
Price: $131.25MSRP: $175

Johnston & Murphy - Bolivar Plain Toe Boots. Color Snuff Italian Suede. On sale for $142.50. MSRP $285.00. 50% off.

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: $142.50MSRP: $285

Frye - Tyler Flex Chelsea. Color Cognac. Low Stock. On sale for $80.40. MSRP $268.00. 70% off. 3.8 out of 5 stars

Low Stock

Frye Tyler Flex Chelsea

Frye Tyler Flex Chelsea

Brand Name: Frye
Product Name: Tyler Flex Chelsea
Gender: Men's
Color: Cognac
Price: $80.40MSRP: $268

Clarks - Burchill Up. Color Dark Brown Leather. On sale for $69.13. MSRP $110.00. 37% off. 5.0 out of 5 stars

Clarks Burchill Up

Clarks Burchill Up

Brand Name: Clarks
Product Name: Burchill Up
Gender: Men's
Color: Dark Brown Leather
Price: $69.13MSRP: $110

Clarks - Burchill Up. Color Black Leather. On sale for $81.82. MSRP $110.00. 26% off. 5.0 out of 5 stars

Clarks Burchill Up

Clarks Burchill Up

Brand Name: Clarks
Product Name: Burchill Up
Gender: Men's
Color: Black Leather
Price: $81.82MSRP: $110

Taft - Lewis. Color Oro Viejo. Low Stock. On sale for $314.10. MSRP $349.00. 10% off. 4.8 out of 5 stars

Low Stock

Taft Lewis

Taft Lewis

Brand Name: Taft
Product Name: Lewis
Gender: Men's
Color: Oro Viejo
Price: $314.10MSRP: $349

Taft - Rome. Color Marron Viejo. On sale for $265.50. MSRP $295.00. 10% off. 4.8 out of 5 stars

Taft Rome

Taft Rome

Brand Name: Taft
Product Name: Rome
Gender: Men's
Color: Marron Viejo
Price: $265.50MSRP: $295

Taft - Rome. Color Oro Viejo. On sale for $250.75. MSRP $295.00. 15% off. 4.8 out of 5 stars

Taft Rome

Taft Rome

Brand Name: Taft
Product Name: Rome
Gender: Men's
Color: Oro Viejo
Price: $250.75MSRP: $295

Taft - Rome. Color Morado Viejo. On sale for $265.50. MSRP $295.00. 10% off. 4.8 out of 5 stars

Taft Rome

Taft Rome

Brand Name: Taft
Product Name: Rome
Gender: Men's
Color: Morado Viejo
Price: $265.50MSRP: $295

Dr. Martens - 1460 Quad Harness. Color Black. On sale for $147.00. MSRP $210.00. 30% off. 4.7 out of 5 stars

Dr. Martens 1460 Quad Harness

Dr. Martens 1460 Quad Harness

Brand Name: Dr. Martens
Product Name: 1460 Quad Harness
Gender: Unisex
Color: Black
Price: $147MSRP: $210

Polo Ralph Lauren - Ranger Mid Suede & Wool Tweed Boots. Color Tweed Colorblock. Low Stock. On sale for $159.60. MSRP $228.00. 30% off. 5.0 out of 5 stars

Low Stock

Polo Ralph Lauren Ranger Mid Suede & Wool Tweed Boots

Polo Ralph Lauren Ranger Mid Suede & Wool Tweed Boots

Brand Name: Polo Ralph Lauren
Product Name: Ranger Mid Suede & Wool Tweed Boots
Gender: Men's
Color: Tweed Colorblock
Price: $159.60MSRP: $228

KEEN - Targhee Lace High Polar Waterproof Insulated. Color Black/Raven. Low Stock. On sale for $170.95. MSRP $189.95. 10% off. 3.9 out of 5 stars

Low Stock

KEEN Targhee Lace High Polar Waterproof Insulated

KEEN Targhee Lace High Polar Waterproof Insulated

Brand Name: KEEN
Product Name: Targhee Lace High Polar Waterproof Insulated
Gender: Men's
Color: Black/Raven
Price: $170.95MSRP: $189.95

Cole Haan - American Classics Plain Toe Boot Waterproof. Color British Tan/A. Low Stock. On sale for $176.57. MSRP $210.00. 16% off. 4.4 out of 5 stars

Low Stock

Cole Haan American Classics Plain Toe Boot Waterproof

Cole Haan American Classics Plain Toe Boot Waterproof

Brand Name: Cole Haan
Product Name: American Classics Plain Toe Boot Waterproof
Gender: Men's
Color: British Tan/A
Price: $176.57MSRP: $210

ECCO - Prague Plain Toe Tie. Color Cocoa Brown. On sale for $215.95. MSRP $239.95. 10% off.

ECCO Prague Plain Toe Tie

ECCO Prague Plain Toe Tie

Brand Name: ECCO
Product Name: Prague Plain Toe Tie
Gender: Men's
Color: Cocoa Brown
Price: $215.95MSRP: $239.95

ECCO - Prague Plain Toe Tie. Color Taupe. On sale for $212.93. MSRP $239.95. 11% off.

ECCO Prague Plain Toe Tie

ECCO Prague Plain Toe Tie

Brand Name: ECCO
Product Name: Prague Plain Toe Tie
Gender: Men's
Color: Taupe
Price: $212.93MSRP: $239.95

Steve Madden - Millsen. Color Tan. Low Stock. On sale for $39.00. MSRP $130.00. 70% off.

Low Stock

Steve Madden Millsen

Steve Madden Millsen

Brand Name: Steve Madden
Product Name: Millsen
Gender: Men's
Color: Tan
Price: $39MSRP: $130

Carhartt - Frontier Water Resistant Chelsea. Color Mossy Brown. Low Stock. On sale for $97.99. MSRP $139.99. 30% off. 4.0 out of 5 stars

Low Stock

Carhartt Frontier Water Resistant Chelsea

Carhartt Frontier Water Resistant Chelsea

Brand Name: Carhartt
Product Name: Frontier Water Resistant Chelsea
Gender: Men's
Color: Mossy Brown
Price: $97.99MSRP: $139.99

Polo Ralph Lauren - Bryson Boot. Color Black Dress Calf. On sale for $214.20. MSRP $238.00. 10% off. 4.4 out of 5 stars

Polo Ralph Lauren Bryson Boot

Polo Ralph Lauren Bryson Boot

Brand Name: Polo Ralph Lauren
Product Name: Bryson Boot
Gender: Men's
Color: Black Dress Calf
Price: $214.20MSRP: $238

Dune London - Matchin. Color Dark Brown. On sale for $148.50. MSRP $165.00. 10% off.

Dune London Matchin

Dune London Matchin

Brand Name: Dune London
Product Name: Matchin
Gender: Men's
Color: Dark Brown
Price: $148.50MSRP: $165

Dune London - Cashed. Color Taupe. Low Stock. On sale for $144.50. MSRP $170.00. 15% off.

Low Stock

Dune London Cashed

Dune London Cashed

Brand Name: Dune London
Product Name: Cashed
Gender: Men's
Color: Taupe
Price: $144.50MSRP: $170

Dune London - Cashed. Color Brown. On sale for $153.00. MSRP $170.00. 10% off.

Dune London Cashed

Dune London Cashed

Brand Name: Dune London
Product Name: Cashed
Gender: Men's
Color: Brown
Price: $153MSRP: $170

Peter Millar - Camden Chelsea Boots. Color Chocolate. On sale for $245.00. MSRP $350.00. 30% off.

Peter Millar Camden Chelsea Boots

Peter Millar Camden Chelsea Boots

Brand Name: Peter Millar
Product Name: Camden Chelsea Boots
Gender: Men's
Color: Chocolate
Price: $245MSRP: $350

Peter Millar - Camden Chelsea Boots. Color Khaki. On sale for $245.00. MSRP $350.00. 30% off.

Peter Millar Camden Chelsea Boots

Peter Millar Camden Chelsea Boots

Brand Name: Peter Millar
Product Name: Camden Chelsea Boots
Gender: Men's
Color: Khaki
Price: $245MSRP: $350

Peter Millar - Tempest Pebble Grain Boots. Color Chocolate. On sale for $221.25. MSRP $295.00. 25% off.

Peter Millar Tempest Pebble Grain Boots

Peter Millar Tempest Pebble Grain Boots

Brand Name: Peter Millar
Product Name: Tempest Pebble Grain Boots
Gender: Men's
Color: Chocolate
Price: $221.25MSRP: $295

Stacy Adams - Maury Cap Toe Chelsea Boot. Color Chocolate. On sale for $123.25. MSRP $145.00. 15% off. 4.8 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: $123.25MSRP: $145

Cole Haan - Roundhill Grand Chukka Boots. Color Steel Gray Nubuck/Light Natural Waterproof. On sale for $212.08. MSRP $260.00. 18% off. 5.0 out of 5 stars

Cole Haan Roundhill Grand Chukka Boots

Cole Haan Roundhill Grand Chukka Boots

Brand Name: Cole Haan
Product Name: Roundhill Grand Chukka Boots
Gender: Men's
Color: Steel Gray Nubuck/Light Natural Waterproof
Price: $212.08MSRP: $260

Polo Ralph Lauren - Owen Leather Chelsea Boots. Color Black. On sale for $205.20. MSRP $228.00. 10% off. 5.0 out of 5 stars

Polo Ralph Lauren Owen Leather Chelsea Boots

Polo Ralph Lauren Owen Leather Chelsea Boots

Brand Name: Polo Ralph Lauren
Product Name: Owen Leather Chelsea Boots
Gender: Men's
Color: Black
Price: $205.20MSRP: $228

Cole Haan - Chamberlin Grand Cap Toe Boots. Color Black Nubuck/Black Water Resistant. On sale for $120.16. MSRP $150.00. 20% off.

Cole Haan Chamberlin Grand Cap Toe Boots

Cole Haan Chamberlin Grand Cap Toe Boots

Brand Name: Cole Haan
Product Name: Chamberlin Grand Cap Toe Boots
Gender: Men's
Color: Black Nubuck/Black Water Resistant
Price: $120.16MSRP: $150

Dr. Martens - 939. Color Black. On sale for $112.00. MSRP $160.00. 30% off. 3.7 out of 5 stars

Dr. Martens 939

Dr. Martens 939

Brand Name: Dr. Martens
Product Name: 939
Gender: Unisex
Color: Black
Price: $112MSRP: $160

Stacy Adams - Bradley Chelsea Boot. Color Black. Low Stock. On sale for $138.03. MSRP $160.00. 14% off. 4.5 out of 5 stars

Low Stock

Stacy Adams Bradley Chelsea Boot

Stacy Adams Bradley Chelsea Boot

Brand Name: Stacy Adams
Product Name: Bradley Chelsea Boot
Gender: Men's
Color: Black
Price: $138.03MSRP: $160

Cole Haan - Chamberlin Grand Chukka Boots. Color Toasted Coconut/Dark Natural/Java Suede. On sale for $136.00. MSRP $160.00. 15% off. 4.5 out of 5 stars

Cole Haan Chamberlin Grand Chukka Boots

Cole Haan Chamberlin Grand Chukka Boots

Brand Name: Cole Haan
Product Name: Chamberlin Grand Chukka Boots
Gender: Men's
Color: Toasted Coconut/Dark Natural/Java Suede
Price: $136MSRP: $160