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Boots on Sale $50 & Under

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Size 9.5 Ankle Leather Products

57 items found

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Kamik - Spencer Mid. Color Black. On sale for $74.98. MSRP $124.98. 40% off. 3.7 out of 5 stars

Kamik Spencer Mid

Kamik Spencer Mid

Brand Name: Kamik
Product Name: Spencer Mid
Gender: Men's
Color: Black
Price: $74.98MSRP: $124.98

SOREL - Cyprus Boot Waterproof. Color Khaki Ii/Jet. $135.00. 4.3 out of 5 stars

SOREL Cyprus Boot Waterproof

SOREL Cyprus Boot Waterproof

Brand Name: SOREL
Product Name: Cyprus Boot Waterproof
Gender: Men's
Color: Khaki Ii/Jet
Price: $135

Birkenstock - Highwood Deep Blue. Color Graphite. On sale for $100.00. MSRP $200.00. 50% off. 4.3 out of 5 stars

Birkenstock Highwood Deep Blue

Birkenstock Highwood Deep Blue

Brand Name: Birkenstock
Product Name: Highwood Deep Blue
Gender: Men's
Color: Graphite
Price: $100MSRP: $200

Oboz - Sawtooth X Mid B-DRY. Color Charcoal. On sale for $180.00. MSRP $200.00. 10% off. 4.1 out of 5 stars

Oboz Sawtooth X Mid B-DRY

Oboz Sawtooth X Mid B-DRY

Brand Name: Oboz
Product Name: Sawtooth X Mid B-DRY
Gender: Men's
Color: Charcoal
Price: $180MSRP: $200

Merrell - Wrapt Sneakers Mid Waterproof. Color Coffee. On sale for $90.00. MSRP $150.00. 40% off. 2.0 out of 5 stars

Merrell Wrapt Sneakers Mid Waterproof

Merrell Wrapt Sneakers Mid Waterproof

Brand Name: Merrell
Product Name: Wrapt Sneakers Mid Waterproof
Gender: Men's
Color: Coffee
Price: $90MSRP: $150

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

Dunham - Brisco. Color Black Leather. On sale for $134.62. MSRP $159.95. 16% off. 4.0 out of 5 stars

Dunham Brisco

Dunham Brisco

Brand Name: Dunham
Product Name: Brisco
Gender: Men's
Color: Black Leather
Price: $134.62MSRP: $159.95

Birkenstock - Highwood Deep Blue. Color Black. On sale for $136.50. MSRP $210.00. 35% off. 4.3 out of 5 stars

Birkenstock Highwood Deep Blue

Birkenstock Highwood Deep Blue

Brand Name: Birkenstock
Product Name: Highwood Deep Blue
Gender: Men's
Color: Black
Price: $136.50MSRP: $210

TOMS - Travel Lite Forrest. Color Tan. On sale for $58.50. MSRP $130.00. 55% off. 5.0 out of 5 stars

TOMS Travel Lite Forrest

TOMS Travel Lite Forrest

Brand Name: TOMS
Product Name: Travel Lite Forrest
Gender: Men's
Color: Tan
Price: $58.50MSRP: $130

TOMS - Travel Lite Forrest. Color Brown. On sale for $65.00. MSRP $130.00. 50% off. 5.0 out of 5 stars

TOMS Travel Lite Forrest

TOMS Travel Lite Forrest

Brand Name: TOMS
Product Name: Travel Lite Forrest
Gender: Men's
Color: Brown
Price: $65MSRP: $130

Born - Ryker. Color Brown (Wood). On sale for $75.00. MSRP $150.00. 50% off. 1.0 out of 5 stars

Born Ryker

Born Ryker

Brand Name: Born
Product Name: Ryker
Gender: Men's
Color: Brown (Wood)
Price: $75MSRP: $150

The North Face - Back-To-Berkeley IV Textile WP. Color Thyme/Utility Brown. Low Stock. On sale for $111.75. MSRP $149.00. 25% off. 4.5 out of 5 stars

Low Stock

The North Face Back-To-Berkeley IV Textile WP

The North Face Back-To-Berkeley IV Textile WP

Brand Name: The North Face
Product Name: Back-To-Berkeley IV Textile WP
Gender: Men's
Color: Thyme/Utility Brown
Price: $111.75MSRP: $149

Kenneth Cole - Tully Chelsea Boots. Color Black Leather. On sale for $98.37. MSRP $184.95. 47% 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: $98.37MSRP: $184.95

SOREL - Slabtown 62' Six Waterproof. Color Canoe/Bleached Ceramic. Low Stock. On sale for $87.50. MSRP $175.00. 50% off.

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: Canoe/Bleached Ceramic
Price: $87.50MSRP: $175

Kenneth Cole - Tully Chelsea Boots. Color Medium Brown Leather. On sale for $127.39. MSRP $184.95. 31% 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: $127.39MSRP: $184.95

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

Merrell - Moab Adventure 3 Mid WP. Color Black. Low Stock. On sale for $144.00. MSRP $160.00. 10% off. 3.6 out of 5 stars

Low Stock

Merrell Moab Adventure 3 Mid WP

Merrell Moab Adventure 3 Mid WP

Brand Name: Merrell
Product Name: Moab Adventure 3 Mid WP
Gender: Men's
Color: Black
Price: $144MSRP: $160

Dr. Scholl's - Madison Men's Chukka. Color Mocha Taupe Textured Nubuck. Low Stock. On sale for $70.10. MSRP $115.00. 39% off. 5.0 out of 5 stars

Low Stock

Dr. Scholl's Madison Men's Chukka

Dr. Scholl's Madison Men's Chukka

Brand Name: Dr. Scholl's
Product Name: Madison Men's Chukka
Gender: Men's
Color: Mocha Taupe Textured Nubuck
Price: $70.10MSRP: $115

Oboz - Burke Mid Leather B-Dry. Color Olive Branch. Low Stock. On sale for $115.50. MSRP $165.00. 30% off. 4.0 out of 5 stars

Low Stock

Oboz Burke Mid Leather B-Dry

Oboz Burke Mid Leather B-Dry

Brand Name: Oboz
Product Name: Burke Mid Leather B-Dry
Gender: Men's
Color: Olive Branch
Price: $115.50MSRP: $165

Oboz - Burke Mid Leather B-Dry. Color Black Sea. Low Stock. On sale for $74.25. MSRP $165.00. 55% off. 4.0 out of 5 stars

Low Stock

Oboz Burke Mid Leather B-Dry

Oboz Burke Mid Leather B-Dry

Brand Name: Oboz
Product Name: Burke Mid Leather B-Dry
Gender: Men's
Color: Black Sea
Price: $74.25MSRP: $165

Oboz - Sawtooth X Mid B-DRY. Color Sandhill. Low Stock. On sale for $126.00. MSRP $180.00. 30% off. 4.1 out of 5 stars

Low Stock

Oboz Sawtooth X Mid B-DRY

Oboz Sawtooth X Mid B-DRY

Brand Name: Oboz
Product Name: Sawtooth X Mid B-DRY
Gender: Men's
Color: Sandhill
Price: $126MSRP: $180

SOREL - Slabtown 62'™ Six Waterproof. Color Wet Sand/Bleached Ceramic. Low Stock. $175.00. 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: Wet Sand/Bleached Ceramic
Price: $175

Rockport - Weather or Not Waterproof Plain Toe Boot. Color New Tan. On sale for $129.95. MSRP $169.95. 24% off. 3.8 out of 5 stars

Rockport Weather or Not Waterproof Plain Toe Boot

Rockport Weather or Not Waterproof Plain Toe Boot

Brand Name: Rockport
Product Name: Weather or Not Waterproof Plain Toe Boot
Gender: Men's
Color: New Tan
Price: $129.95MSRP: $169.95

Sperry - Newton Boots. Color Taupe. On sale for $115.50. MSRP $165.00. 30% off. 5.0 out of 5 stars

Sperry Newton Boots

Sperry Newton Boots

Brand Name: Sperry
Product Name: Newton Boots
Gender: Men's
Color: Taupe
Price: $115.50MSRP: $165

Sperry - Mini Lug Chukka. Color Other Brown. On sale for $75.00. MSRP $150.00. 50% off.

Sperry Mini Lug Chukka

Sperry Mini Lug Chukka

Brand Name: Sperry
Product Name: Mini Lug Chukka
Gender: Men's
Color: Other Brown
Price: $75MSRP: $150

Deer Stags - Bangor. Color Redwood/Dark Brown. On sale for $51.01. MSRP $90.00. 43% off. 3.9 out of 5 stars

Deer Stags Bangor

Deer Stags Bangor

Brand Name: Deer Stags
Product Name: Bangor
Gender: Men's
Color: Redwood/Dark Brown
Price: $51.01MSRP: $90

Oboz - Burke Mid Leather B-Dry. Color Grizzly. On sale for $107.25. MSRP $165.00. 35% off. 4.0 out of 5 stars

Oboz Burke Mid Leather B-Dry

Oboz Burke Mid Leather B-Dry

Brand Name: Oboz
Product Name: Burke Mid Leather B-Dry
Gender: Men's
Color: Grizzly
Price: $107.25MSRP: $165

Timberland PRO - Reaxion Mid Composite Safety Toe Waterproof. Color Black/Grey. $170.00. 4.1 out of 5 stars

Timberland PRO Reaxion Mid Composite Safety Toe Waterproof

Timberland PRO Reaxion Mid Composite Safety Toe Waterproof

Brand Name: Timberland PRO
Product Name: Reaxion Mid Composite Safety Toe Waterproof
Gender: Men's
Color: Black/Grey
Price: $170

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

Dunham - Alpine Mid Boots. Color Black Leather. $164.74. 3.4 out of 5 stars

Dunham Alpine Mid Boots

Dunham Alpine Mid Boots

Brand Name: Dunham
Product Name: Alpine Mid Boots
Gender: Men's
Color: Black Leather
Price: $164.74

Dunham - Alpine Mid Boots. Color Dark Brown Leather. $164.95. 3.4 out of 5 stars

Dunham Alpine Mid Boots

Dunham Alpine Mid Boots

Brand Name: Dunham
Product Name: Alpine Mid Boots
Gender: Men's
Color: Dark Brown Leather
Price: $164.95

Dunham - Alpine Mid Boots. Color Dark Taupe Leather. $164.95. 3.4 out of 5 stars

Dunham Alpine Mid Boots

Dunham Alpine Mid Boots

Brand Name: Dunham
Product Name: Alpine Mid Boots
Gender: Men's
Color: Dark Taupe Leather
Price: $164.95

Dunham - Brisco. Color Dark Brown Leather. On sale for $144.67. MSRP $159.95. 10% off. 4.0 out of 5 stars

Dunham Brisco

Dunham Brisco

Brand Name: Dunham
Product Name: Brisco
Gender: Men's
Color: Dark Brown Leather
Price: $144.67MSRP: $159.95

Rockport - Ezra Waterproof Boots. Color Taupe Leather. On sale for $113.34. MSRP $159.95. 29% off. 2.8 out of 5 stars

Rockport Ezra Waterproof Boots

Rockport Ezra Waterproof Boots

Brand Name: Rockport
Product Name: Ezra Waterproof Boots
Gender: Men's
Color: Taupe Leather
Price: $113.34MSRP: $159.95

Clarks - Steadwell Mid. Color Black Leather. On sale for $72.50. MSRP $110.00. 34% off. 5.0 out of 5 stars

Clarks Steadwell Mid

Clarks Steadwell Mid

Brand Name: Clarks
Product Name: Steadwell Mid
Gender: Men's
Color: Black Leather
Price: $72.50MSRP: $110

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

Birkenstock - Highwood Deep Blue. Color Dark Tea. On sale for $105.00. MSRP $210.00. 50% off. 4.3 out of 5 stars

Birkenstock Highwood Deep Blue

Birkenstock Highwood Deep Blue

Brand Name: Birkenstock
Product Name: Highwood Deep Blue
Gender: Men's
Color: Dark Tea
Price: $105MSRP: $210

Merrell - Moab 3 Mid Wp. Color Talc. On sale for $168.50. MSRP $170.00. 1% off. 4.4 out of 5 stars

Merrell Moab 3 Mid Wp

Merrell Moab 3 Mid Wp

Brand Name: Merrell
Product Name: Moab 3 Mid Wp
Gender: Men's
Color: Talc
Price: $168.50MSRP: $170

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

ECCO - Metropole Milan Chukka Boots. Color Camel Suede. On sale for $146.21. MSRP $194.95. 25% off. 4.0 out of 5 stars

ECCO Metropole Milan Chukka Boots

ECCO Metropole Milan Chukka Boots

Brand Name: ECCO
Product Name: Metropole Milan Chukka Boots
Gender: Men's
Color: Camel Suede
Price: $146.21MSRP: $194.95

Born - Ryker. Color Black. On sale for $82.50. MSRP $150.00. 45% off. 1.0 out of 5 stars

Born Ryker

Born Ryker

Brand Name: Born
Product Name: Ryker
Gender: Men's
Color: Black
Price: $82.50MSRP: $150

Merrell - Alpine 83 Sneaker Recraft Mid Waterproof. Color Black. Low Stock. On sale for $119.37. MSRP $135.00. 12% off. 3.4 out of 5 stars

Low Stock

Merrell Alpine 83 Sneaker Recraft Mid Waterproof

Merrell Alpine 83 Sneaker Recraft Mid Waterproof

Brand Name: Merrell
Product Name: Alpine 83 Sneaker Recraft Mid Waterproof
Gender: Men's
Color: Black
Price: $119.37MSRP: $135

Born - Reed. Color Black. Low Stock. On sale for $75.00. MSRP $150.00. 50% off. 4.8 out of 5 stars

Low Stock

Born Reed

Born Reed

Brand Name: Born
Product Name: Reed
Gender: Men's
Color: Black
Price: $75MSRP: $150

Born - Reed. Color Chocolate (Espresso). On sale for $90.00. MSRP $150.00. 40% off. 4.8 out of 5 stars

Born Reed

Born Reed

Brand Name: Born
Product Name: Reed
Gender: Men's
Color: Chocolate (Espresso)
Price: $90MSRP: $150

The North Face - Back-To-Berkeley IV Textile WP. Color None. On sale for $134.10. MSRP $149.00. 10% off. 4.5 out of 5 stars

The North Face Back-To-Berkeley IV Textile WP

The North Face Back-To-Berkeley IV Textile WP

Brand Name: The North Face
Product Name: Back-To-Berkeley IV Textile WP
Gender: Men's
Color: None
Price: $134.10MSRP: $149

Birkenstock - Highwood Mid Lace-Up Deep Blue - Leather. Color Black. Low Stock. On sale for $160.00. MSRP $200.00. 20% off. 4.0 out of 5 stars

Low Stock

Birkenstock Highwood Mid Lace-Up Deep Blue - Leather

Birkenstock Highwood Mid Lace-Up Deep Blue - Leather

Brand Name: Birkenstock
Product Name: Highwood Mid Lace-Up Deep Blue - Leather
Gender: Men's
Color: Black
Price: $160MSRP: $200

Cole Haan - Muir Moc Tall Boots. Color Raven Suede/Raven Waterproof. On sale for $114.40. MSRP $208.00. 45% off. 5.0 out of 5 stars

Cole Haan Muir Moc Tall Boots

Cole Haan Muir Moc Tall Boots

Brand Name: Cole Haan
Product Name: Muir Moc Tall Boots
Gender: Men's
Color: Raven Suede/Raven Waterproof
Price: $114.40MSRP: $208

Kenneth Cole - Todd. Color Dark Brown Leather. On sale for $163.99. MSRP $218.95. 25% off. 3.0 out of 5 stars

Kenneth Cole Todd

Kenneth Cole Todd

Brand Name: Kenneth Cole
Product Name: Todd
Gender: Men's
Color: Dark Brown Leather
Price: $163.99MSRP: $218.95

Stacy Adams - Maury Cap Toe Chelsea Boot. Color Chocolate. Low Stock. On sale for $94.52. MSRP $145.00. 35% 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: $94.52MSRP: $145

Kenneth Cole - Frank. Color Black Leather. On sale for $132.44. MSRP $184.95. 28% off.

Kenneth Cole Frank

Kenneth Cole Frank

Brand Name: Kenneth Cole
Product Name: Frank
Gender: Men's
Color: Black Leather
Price: $132.44MSRP: $184.95

Kenneth Cole - Frank. Color Light Brown Leather. On sale for $97.59. MSRP $184.95. 47% off.

Kenneth Cole Frank

Kenneth Cole Frank

Brand Name: Kenneth Cole
Product Name: Frank
Gender: Men's
Color: Light Brown Leather
Price: $97.59MSRP: $184.95

Clarks - Bushacre 3. Color Dark Brown Leather. On sale for $74.98. MSRP $110.00. 32% off. 3.9 out of 5 stars

Clarks Bushacre 3

Clarks Bushacre 3

Brand Name: Clarks
Product Name: Bushacre 3
Gender: Men's
Color: Dark Brown Leather
Price: $74.98MSRP: $110

KEEN - Hightrail Waterproof Hiking Boot. Color Steel Grey/ForeST Night. On sale for $134.65. MSRP $154.95. 13% off. 4.3 out of 5 stars

KEEN Hightrail Waterproof Hiking Boot

KEEN Hightrail Waterproof Hiking Boot

Brand Name: KEEN
Product Name: Hightrail Waterproof Hiking Boot
Gender: Men's
Color: Steel Grey/ForeST Night
Price: $134.65MSRP: $154.95

SOREL - Outing Nw Sneaker Mid Waterproof. Color Utility Green/Black. $120.00. 4.1 out of 5 stars

SOREL Outing Nw Sneaker Mid Waterproof

SOREL Outing Nw Sneaker Mid Waterproof

Brand Name: SOREL
Product Name: Outing Nw Sneaker Mid Waterproof
Gender: Men's
Color: Utility Green/Black
Price: $120

SOREL - Madson II Chukka Waterproof. Color Velvet Tan/Gum. $190.00.

SOREL Madson II Chukka Waterproof

SOREL Madson II Chukka Waterproof

Brand Name: SOREL
Product Name: Madson II Chukka Waterproof
Gender: Men's
Color: Velvet Tan/Gum
Price: $190

SOREL - Outing Nw Sneaker Mid Waterproof. Color Khaki Ii/Jet. $120.00. 4.1 out of 5 stars

SOREL Outing Nw Sneaker Mid Waterproof

SOREL Outing Nw Sneaker Mid Waterproof

Brand Name: SOREL
Product Name: Outing Nw Sneaker Mid Waterproof
Gender: Men's
Color: Khaki Ii/Jet
Price: $120