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Boots on Sale $50 & Under

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Size 10.5 Ankle Leather Products

56 items found

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Kamik - Spencer Mid. Color Black. On sale for $49.99. MSRP $124.98. 60% off. 3.4 out of 5 stars

Kamik Spencer Mid

Kamik Spencer Mid

Brand Name: Kamik
Product Name: Spencer Mid
Gender: Men's
Color: Black
Price: $49.99MSRP: $124.98

Sperry - Avenue Duck Boot. Color Black/Amaretto. On sale for $83.85. MSRP $120.00. 30% off. 4.1 out of 5 stars

Sperry Avenue Duck Boot

Sperry Avenue Duck Boot

Brand Name: Sperry
Product Name: Avenue Duck Boot
Gender: Men's
Color: Black/Amaretto
Price: $83.85MSRP: $120

Rockport - Ezra Waterproof Boots. Color Taupe Leather. On sale for $104.60. MSRP $159.95. 35% off. 2.4 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: $104.60MSRP: $159.95

Rockport - Northfield Waterproof Boots. Color Chocolate. On sale for $119.95. MSRP $159.95. 25% off. 4.3 out of 5 stars

Rockport Northfield Waterproof Boots

Rockport Northfield Waterproof Boots

Brand Name: Rockport
Product Name: Northfield Waterproof Boots
Gender: Men's
Color: Chocolate
Price: $119.95MSRP: $159.95

adidas - Terrex Trailmaker 2 Leather Hiking Shoes. Color Wonder Beige/Wonder Beige/Charcoal. On sale for $97.82. MSRP $130.00. 25% off. 4.5 out of 5 stars

adidas Terrex Trailmaker 2 Leather Hiking Shoes

adidas Terrex Trailmaker 2 Leather Hiking Shoes

Brand Name: adidas
Product Name: Terrex Trailmaker 2 Leather Hiking Shoes
Gender: Men's
Color: Wonder Beige/Wonder Beige/Charcoal
Price: $97.82MSRP: $130

Rockport - Ezra Waterproof Boots. Color Black Leather. On sale for $126.64. MSRP $159.95. 21% off. 2.4 out of 5 stars

Rockport Ezra Waterproof Boots

Rockport Ezra Waterproof Boots

Brand Name: Rockport
Product Name: Ezra Waterproof Boots
Gender: Men's
Color: Black Leather
Price: $126.64MSRP: $159.95

Frye - Barrett Lace Up. Color Cognac. On sale for $173.60. MSRP $248.00. 30% off. 5.0 out of 5 stars

Frye Barrett Lace Up

Frye Barrett Lace Up

Brand Name: Frye
Product Name: Barrett Lace Up
Gender: Men's
Color: Cognac
Price: $173.60MSRP: $248

Frye - Paul Chukka. Color Brown. Low Stock. On sale for $169.20. MSRP $188.00. 10% off. 4.0 out of 5 stars

Low Stock

Frye Paul Chukka

Frye Paul Chukka

Brand Name: Frye
Product Name: Paul Chukka
Gender: Men's
Color: Brown
Price: $169.20MSRP: $188

Dunham - Brisco. Color Black Leather. On sale for $128.01. MSRP $159.95. 20% off. 4.0 out of 5 stars

Dunham Brisco

Dunham Brisco

Brand Name: Dunham
Product Name: Brisco
Gender: Men's
Color: Black Leather
Price: $128.01MSRP: $159.95

ECCO - Metropole Milan Chukka Boots. Color Camel Suede. On sale for $138.34. MSRP $194.95. 29% 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: $138.34MSRP: $194.95

Kenneth Cole - Todd. Color Dark Brown Leather. On sale for $150.21. MSRP $218.95. 31% off.

Kenneth Cole Todd

Kenneth Cole Todd

Brand Name: Kenneth Cole
Product Name: Todd
Gender: Men's
Color: Dark Brown Leather
Price: $150.21MSRP: $218.95

Kamik - Spencer Mid. Color Black/Gum. On sale for $93.73. MSRP $124.98. 25% off. 3.4 out of 5 stars

Kamik Spencer Mid

Kamik Spencer Mid

Brand Name: Kamik
Product Name: Spencer Mid
Gender: Men's
Color: Black/Gum
Price: $93.73MSRP: $124.98

Clarks - Steadwell Mid. Color Black Leather. On sale for $99.00. MSRP $110.00. 10% off.

Clarks Steadwell Mid

Clarks Steadwell Mid

Brand Name: Clarks
Product Name: Steadwell Mid
Gender: Men's
Color: Black Leather
Price: $99MSRP: $110

Merrell - Moab 3 Mid Waterproof. Color Latte. On sale for $118.99. MSRP $170.00. 30% off. 4.4 out of 5 stars

Merrell Moab 3 Mid Waterproof

Merrell Moab 3 Mid Waterproof

Brand Name: Merrell
Product Name: Moab 3 Mid Waterproof
Gender: Men's
Color: Latte
Price: $118.99MSRP: $170

TOMS - Travel Lite Forrest. Color Tan. On sale for $58.50. MSRP $130.00. 55% off.

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

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

KEEN Utility - San Jose 6” Alloy Toe Waterproof 90 Degree Heel. Color Bistre/Gum. $175.00. 3.0 out of 5 stars

KEEN Utility San Jose 6” Alloy Toe Waterproof 90 Degree Heel

KEEN Utility San Jose 6” Alloy Toe Waterproof 90 Degree Heel

Brand Name: KEEN Utility
Product Name: San Jose 6” Alloy Toe Waterproof 90 Degree Heel
Gender: Men's
Color: Bistre/Gum
Price: $175

adidas - Terrex Trailmaker 2 Leather Hiking Shoes. Color Olive Strata/Olive Strata/Silver Pebble. On sale for $103.93. MSRP $130.00. 20% off. 4.5 out of 5 stars

adidas Terrex Trailmaker 2 Leather Hiking Shoes

adidas Terrex Trailmaker 2 Leather Hiking Shoes

Brand Name: adidas
Product Name: Terrex Trailmaker 2 Leather Hiking Shoes
Gender: Men's
Color: Olive Strata/Olive Strata/Silver Pebble
Price: $103.93MSRP: $130

Dunham - Alpine Mid Boots. Color Black Leather. On sale for $152.46. MSRP $164.95. 8% off. 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: $152.46MSRP: $164.95

Dunham - Alpine Mid Boots. Color Dark Brown Leather. On sale for $163.09. MSRP $164.95. 1% off. 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: $163.09MSRP: $164.95

Dunham - Alpine Mid Boots. Color Dark Taupe Leather. On sale for $145.95. MSRP $164.95. 12% off. 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: $145.95MSRP: $164.95

Dunham - Brisco. Color Dark Brown Leather. On sale for $136.67. MSRP $159.95. 15% 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: $136.67MSRP: $159.95

Martin Dingman - Huntley Chelsea Boot. Color Walnut. Low Stock. On sale for $315.00. MSRP $350.00. 10% off.

Low Stock

Martin Dingman Huntley Chelsea Boot

Martin Dingman Huntley Chelsea Boot

Brand Name: Martin Dingman
Product Name: Huntley Chelsea Boot
Gender: Men's
Color: Walnut
Price: $315MSRP: $350

Stacy Adams - Maxwell Plain Toe Demi Boot. Color Cognac. On sale for $103.66. MSRP $125.00. 17% off. 4.6 out of 5 stars

Stacy Adams Maxwell Plain Toe Demi Boot

Stacy Adams Maxwell Plain Toe Demi Boot

Brand Name: Stacy Adams
Product Name: Maxwell Plain Toe Demi Boot
Gender: Men's
Color: Cognac
Price: $103.66MSRP: $125

Peter Millar - Tempest Boots. Color Beach. Low Stock. On sale for $236.00. MSRP $295.00. 20% off.

Low Stock

Peter Millar Tempest Boots

Peter Millar Tempest Boots

Brand Name: Peter Millar
Product Name: Tempest Boots
Gender: Men's
Color: Beach
Price: $236MSRP: $295

Columbia - Landroamer Explorer Waterproof. Color Grill/Desert Sun. Low Stock. On sale for $92.33. MSRP $120.00. 23% off. 3.8 out of 5 stars

Low Stock

Columbia Landroamer Explorer Waterproof

Columbia Landroamer Explorer Waterproof

Brand Name: Columbia
Product Name: Landroamer Explorer Waterproof
Gender: Men's
Color: Grill/Desert Sun
Price: $92.33MSRP: $120

Columbia - Landroamer Explorer Waterproof. Color Black/Dark Grey. On sale for $90.00. MSRP $120.00. 25% off. 3.8 out of 5 stars

Columbia Landroamer Explorer Waterproof

Columbia Landroamer Explorer Waterproof

Brand Name: Columbia
Product Name: Landroamer Explorer Waterproof
Gender: Men's
Color: Black/Dark Grey
Price: $90MSRP: $120

Rockport - Flynn. Color Medium Natural Leather. On sale for $119.96. MSRP $159.95. 25% off. 2.8 out of 5 stars

Rockport Flynn

Rockport Flynn

Brand Name: Rockport
Product Name: Flynn
Gender: Men's
Color: Medium Natural Leather
Price: $119.96MSRP: $159.95

Merrell - Moab 3 Mid Waterproof. Color Grey Stone. On sale for $126.93. MSRP $170.00. 25% off. 4.4 out of 5 stars

Merrell Moab 3 Mid Waterproof

Merrell Moab 3 Mid Waterproof

Brand Name: Merrell
Product Name: Moab 3 Mid Waterproof
Gender: Men's
Color: Grey Stone
Price: $126.93MSRP: $170

Eastland 1955 Edition - Chimney Pond. Color Black. On sale for $108.75. MSRP $145.00. 25% off. 5.0 out of 5 stars

Eastland 1955 Edition Chimney Pond

Eastland 1955 Edition Chimney Pond

Brand Name: Eastland 1955 Edition
Product Name: Chimney Pond
Gender: Men's
Color: Black
Price: $108.75MSRP: $145

TOMS - Travel Lite Forrest. Color Brown. On sale for $78.00. MSRP $130.00. 40% off.

TOMS Travel Lite Forrest

TOMS Travel Lite Forrest

Brand Name: TOMS
Product Name: Travel Lite Forrest
Gender: Men's
Color: Brown
Price: $78MSRP: $130

Polo Ralph Lauren - Ranger Mid Camo Suede Boot. Color Black/Camo. $198.00.

Polo Ralph Lauren Ranger Mid Camo Suede Boot

Polo Ralph Lauren Ranger Mid Camo Suede Boot

Brand Name: Polo Ralph Lauren
Product Name: Ranger Mid Camo Suede Boot
Gender: Men's
Color: Black/Camo
Price: $198

Cole Haan - American Classics Plain Toe Boot Waterproof. Color Black/Black Waterproof. Low Stock. On sale for $149.95. MSRP $210.00. 29% 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: Black/Black Waterproof
Price: $149.95MSRP: $210

Magnanni - Borazo. Color Taupe/Grey. Low Stock. On sale for $374.25. MSRP $499.00. 25% off.

Low Stock

Magnanni Borazo

Magnanni Borazo

Brand Name: Magnanni
Product Name: Borazo
Gender: Men's
Color: Taupe/Grey
Price: $374.25MSRP: $499

Nisolo - All-Weather Chelsea Boot. Color Dark Tobacco. On sale for $104.00. MSRP $260.00. 60% off. 2.0 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

KEEN Utility - Camden 8" Waterproof 600G (Comp Toe). Color Leather Brown/Black. $235.00. 3.9 out of 5 stars

KEEN Utility Camden 8" Waterproof 600G (Comp Toe)

KEEN Utility Camden 8" Waterproof 600G (Comp Toe)

Brand Name: KEEN Utility
Product Name: Camden 8" Waterproof 600G (Comp Toe)
Gender: Men's
Color: Leather Brown/Black
Price: $235

Johnston & Murphy - Bolivar Plain Toe Boots. Color Snuff Italian Suede. Low Stock. On sale for $179.97. MSRP $285.00. 37% off.

Low Stock

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: $179.97MSRP: $285

Propet - Veymont. Color Gunsmoke. Low Stock. On sale for $134.36. MSRP $169.95. 21% off. 3.4 out of 5 stars

Low Stock

Propet Veymont

Propet Veymont

Brand Name: Propet
Product Name: Veymont
Gender: Men's
Color: Gunsmoke
Price: $134.36MSRP: $169.95

Martin Dingman - Old Row Wingtip. Color Cigar. Low Stock. On sale for $276.50. MSRP $395.00. 30% off.

Low Stock

Martin Dingman Old Row Wingtip

Martin Dingman Old Row Wingtip

Brand Name: Martin Dingman
Product Name: Old Row Wingtip
Gender: Men's
Color: Cigar
Price: $276.50MSRP: $395

Sperry - Newton Boots. Color Taupe. On sale for $148.50. MSRP $165.00. 10% off.

Sperry Newton Boots

Sperry Newton Boots

Brand Name: Sperry
Product Name: Newton Boots
Gender: Men's
Color: Taupe
Price: $148.50MSRP: $165

Sperry - Stringer. Color Tan. On sale for $117.00. MSRP $130.00. 10% off.

Sperry Stringer

Sperry Stringer

Brand Name: Sperry
Product Name: Stringer
Gender: Men's
Color: Tan
Price: $117MSRP: $130

Frye - Tyler Flex Chelsea. Color Black. On sale for $201.00. MSRP $268.00. 25% off. 3.5 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

Frye - Barrett Lace Up. Color Black. On sale for $223.20. MSRP $248.00. 10% off. 5.0 out of 5 stars

Frye Barrett Lace Up

Frye Barrett Lace Up

Brand Name: Frye
Product Name: Barrett Lace Up
Gender: Men's
Color: Black
Price: $223.20MSRP: $248

Propet - Veymont. Color Grey/Blue. On sale for $128.00. MSRP $169.95. 25% off. 3.4 out of 5 stars

Propet Veymont

Propet Veymont

Brand Name: Propet
Product Name: Veymont
Gender: Men's
Color: Grey/Blue
Price: $128MSRP: $169.95

Martin Dingman - Piney Creek Chukka. Color Khaki. Low Stock. On sale for $292.50. MSRP $325.00. 10% off.

Low Stock

Martin Dingman Piney Creek Chukka

Martin Dingman Piney Creek Chukka

Brand Name: Martin Dingman
Product Name: Piney Creek Chukka
Gender: Men's
Color: Khaki
Price: $292.50MSRP: $325

Nunn Bush - Odell Wingtip Boot with KORE Walking Comfort Technology. Color Black Tumbled. Low Stock. On sale for $80.50. MSRP $115.00. 30% off. 4.2 out of 5 stars

Low Stock

Nunn Bush Odell Wingtip Boot with KORE Walking Comfort Technology

Nunn Bush Odell Wingtip Boot with KORE Walking Comfort Technology

Brand Name: Nunn Bush
Product Name: Odell Wingtip Boot with KORE Walking Comfort Technology
Gender: Men's
Color: Black Tumbled
Price: $80.50MSRP: $115

Cole Haan - Originalgrand Remastered Waterproof Chukka Boots. Color Black/Black. On sale for $159.95. MSRP $200.00. 20% off. 2.7 out of 5 stars

Cole Haan Originalgrand Remastered Waterproof Chukka Boots

Cole Haan Originalgrand Remastered Waterproof Chukka Boots

Brand Name: Cole Haan
Product Name: Originalgrand Remastered Waterproof Chukka Boots
Gender: Men's
Color: Black/Black
Price: $159.95MSRP: $200

Cole Haan - Originalgrand Remastered Waterproof Chukka Boots. Color Woodbury/Dark Roast. Low Stock. On sale for $159.95. MSRP $200.00. 20% off. 2.7 out of 5 stars

Low Stock

Cole Haan Originalgrand Remastered Waterproof Chukka Boots

Cole Haan Originalgrand Remastered Waterproof Chukka Boots

Brand Name: Cole Haan
Product Name: Originalgrand Remastered Waterproof Chukka Boots
Gender: Men's
Color: Woodbury/Dark Roast
Price: $159.95MSRP: $200

Clarks - Shepton. Color Sand Suede. On sale for $71.50. MSRP $110.00. 35% off. 1.7 out of 5 stars

Clarks Shepton

Clarks Shepton

Brand Name: Clarks
Product Name: Shepton
Gender: Men's
Color: Sand Suede
Price: $71.50MSRP: $110

Vince Camuto - Kameil Waterproof Boot. Color Black. Low Stock. On sale for $170.10. MSRP $189.00. 10% off.

Low Stock

Vince Camuto Kameil Waterproof Boot

Vince Camuto Kameil Waterproof Boot

Brand Name: Vince Camuto
Product Name: Kameil Waterproof Boot
Gender: Men's
Color: Black
Price: $170.10MSRP: $189

Cole Haan - Chamberlin Grand Cap Toe Boots. Color Spiced Brown Suede/Water Resistant. On sale for $138.05. MSRP $150.00. 8% 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: Spiced Brown Suede/Water Resistant
Price: $138.05MSRP: $150

Cole Haan - American Classics Chelsea Boots. Color Black Waterproof/Black/Black. Low Stock. On sale for $130.00. MSRP $200.00. 35% 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: $130MSRP: $200

Cole Haan - American Classics Chelsea Boots. Color Morel Nubuck Waterproof/Black. On sale for $119.95. MSRP $200.00. 40% 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: $119.95MSRP: $200

Cole Haan - Muir Moc Tall Boots. Color Raven Suede/Raven Waterproof. On sale for $167.08. MSRP $208.00. 20% off.

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: $167.08MSRP: $208

Propet - Findley. Color Black. On sale for $103.01. MSRP $154.99. 34% off. 3.6 out of 5 stars

Propet Findley

Propet Findley

Brand Name: Propet
Product Name: Findley
Gender: Men's
Color: Black
Price: $103.01MSRP: $154.99

Propet - Findley. Color Tan 1. On sale for $97.66. MSRP $154.99. 37% off. 3.6 out of 5 stars

Propet Findley

Propet Findley

Brand Name: Propet
Product Name: Findley
Gender: Men's
Color: Tan 1
Price: $97.66MSRP: $154.99