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Size 8.5 Leather Boots

652 items found

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Rockport - Ezra Waterproof Boots. Color Dark Brown Leather. $159.95. 2.8 out of 5 stars

Brown Rockport Ezra Waterproof Boots

Brown Rockport Ezra Waterproof Boots

+2

Brand Name: Rockport
Product Name: Ezra Waterproof Boots
Gender: Men's
Color: Dark Brown Leather
Price: $159.95
Rating: 3Rated 3 stars out of 5(6)

Dunham - Brisco. Color Black Leather. On sale for $133.17. MSRP $159.95. 17% off. 4.0 out of 5 stars

Black Dunham Brisco

Black Dunham Brisco

+2

Brand Name: Dunham
Product Name: Brisco
Gender: Men's
Color: Black Leather
Price: $133.17MSRP: $159.9517% OFF
Rating: 4Rated 4 stars out of 5(1)

Clarks - Desert Boots EVO. Color Beeswax Leather. Low Stock. $110.00. 3.3 out of 5 stars

Low Stock

Brown Clarks Desert Boots EVO

Brown Clarks Desert Boots EVO

+3

Brand Name: Clarks
Product Name: Desert Boots EVO
Gender: Men's
Color: Beeswax Leather
Price: $110
Rating: 3Rated 3 stars out of 5(30)

Birkenstock - Highwood Deep Blue. Color Black. On sale for $136.50. MSRP $210.00. 35% off. 4.2 out of 5 stars

Black Birkenstock Highwood Deep Blue

Black Birkenstock Highwood Deep Blue

+4

Brand Name: Birkenstock
Product Name: Highwood Deep Blue
Gender: Men's
Color: Black
Price: $136.50MSRP: $21035% OFF
Rating: 4Rated 4 stars out of 5(9)

Kamik - Spencer Mid. Color Black. On sale for $87.48. MSRP $124.98. 30% off. 3.7 out of 5 stars

Black Kamik Spencer Mid

Black Kamik Spencer Mid

+2

Brand Name: Kamik
Product Name: Spencer Mid
Gender: Men's
Color: Black
Price: $87.48MSRP: $124.9830% OFF
Rating: 4Rated 4 stars out of 5(23)

Bogs - Arcata Urban Leather Chelsea. Color Black. $170.00. 4.2 out of 5 stars

Black Bogs Arcata Urban Leather Chelsea

Black Bogs Arcata Urban Leather Chelsea

+3

Brand Name: Bogs
Product Name: Arcata Urban Leather Chelsea
Gender: Men's
Color: Black
Price: $170
Rating: 4Rated 4 stars out of 5(40)

. Salomon - Quest 4 GTX®. Color Olive Night/Peat/Safari. $230.00. 3.6 out of 5 stars

Olive Salomon Quest 4 GTX®

Olive Salomon Quest 4 GTX®

+2

Brand Name: Salomon
Product Name: Quest 4 GTX®
Gender: Men's
Color: Olive Night/Peat/Safari
Price: $230
Rating: 4Rated 4 stars out of 5(643)

Propet - Blizzard Mid Zip. Color Brown/Black. On sale for $119.95. MSRP $149.99. 20% off. 4.0 out of 5 stars

Brown Propet Blizzard Mid Zip

Brown Propet Blizzard Mid Zip

Brand Name: Propet
Product Name: Blizzard Mid Zip
Gender: Men's
Color: Brown/Black
Price: $119.95MSRP: $149.9920% OFF
Rating: 4Rated 4 stars out of 5(148)

KEEN - Anchorage 4 Waterproof Pull-On Durable Insulated. Color Dark Earth/Black. On sale for $157.45. MSRP $174.95. 10% off. 4.1 out of 5 stars

Brown KEEN Anchorage 4 Waterproof Pull-On Durable Insulated

Brown KEEN Anchorage 4 Waterproof Pull-On Durable Insulated

+2

Brand Name: KEEN
Product Name: Anchorage 4 Waterproof Pull-On Durable Insulated
Gender: Men's
Color: Dark Earth/Black
Price: $157.45MSRP: $174.9510% OFF
Rating: 4Rated 4 stars out of 5(8)

Johnston & Murphy - Xc+ Parker Chukka. Color Brown Waterproof Full Grain. Low Stock. On sale for $116.05. MSRP $189.00. 39% off.

Low Stock

Red Johnston & Murphy Xc+ Parker Chukka

Red Johnston & Murphy Xc+ Parker Chukka

+2

Brand Name: Johnston & Murphy
Product Name: Xc+ Parker Chukka
Gender: Men's
Color: Brown Waterproof Full Grain
Price: $116.05MSRP: $18939% OFF
Rating

Cole Haan - Chamberlin Grand Chelsea Boots. Color Black Nubuck/Black Water Resistant. $150.00.

Black Cole Haan Chamberlin Grand Chelsea Boots

Black Cole Haan Chamberlin Grand Chelsea Boots

+2

Brand Name: Cole Haan
Product Name: Chamberlin Grand Chelsea Boots
Gender: Men's
Color: Black Nubuck/Black Water Resistant
Price: $150
Rating

TOMS - Travel Lite Forrest. Color Brown. On sale for $65.00. MSRP $130.00. 50% off.

Brown TOMS Travel Lite Forrest

Brown TOMS Travel Lite Forrest

+2

Brand Name: TOMS
Product Name: Travel Lite Forrest
Gender: Men's
Color: Brown
Price: $65MSRP: $13050% OFF
Rating

Johnston & Murphy - Barrett Plain Toe Boots. Color Tan Full Grain 1. On sale for $139.30. MSRP $199.00. 30% off. 4.5 out of 5 stars

Brown Johnston & Murphy Barrett Plain Toe Boots

Brown Johnston & Murphy Barrett Plain Toe Boots

Brand Name: Johnston & Murphy
Product Name: Barrett Plain Toe Boots
Gender: Men's
Color: Tan Full Grain 1
Price: $139.30MSRP: $19930% OFF
Rating: 5Rated 5 stars out of 5(131)

ECCO - Metropole Milan Chukka Boots. Color Camel Suede. On sale for $165.70. MSRP $194.95. 15% off. 4.0 out of 5 stars

Tan ECCO Metropole Milan Chukka Boots

Tan ECCO Metropole Milan Chukka Boots

+2

Brand Name: ECCO
Product Name: Metropole Milan Chukka Boots
Gender: Men's
Color: Camel Suede
Price: $165.70MSRP: $194.9515% OFF
Rating: 4Rated 4 stars out of 5(1)

Cole Haan - Zerogrand Remastered Waterproof Chelsea Boots. Color Dark Coffee/Oxford Tan. Low Stock. On sale for $161.00. MSRP $230.00. 30% off.

Low Stock

Brown Cole Haan Zerogrand Remastered Waterproof Chelsea Boots

Brown Cole Haan Zerogrand Remastered Waterproof Chelsea Boots

Brand Name: Cole Haan
Product Name: Zerogrand Remastered Waterproof Chelsea Boots
Gender: Men's
Color: Dark Coffee/Oxford Tan
Price: $161MSRP: $23030% OFF
Rating

Sperry - Mini Lug Chukka. Color Other Beige. $150.00.

Pink Sperry Mini Lug Chukka

Pink Sperry Mini Lug Chukka

+2

Brand Name: Sperry
Product Name: Mini Lug Chukka
Gender: Men's
Color: Other Beige
Price: $150
Rating

Salomon - Crosstrak. Color Asphalt/Black/Sharkskin. Low Stock. $200.00. 3.8 out of 5 stars

Low Stock

Gray Salomon Crosstrak

Gray Salomon Crosstrak

+2

Brand Name: Salomon
Product Name: Crosstrak
Gender: Men's
Color: Asphalt/Black/Sharkskin
Price: $200
Rating: 4Rated 4 stars out of 5(10)

Cole Haan - Judson Grand Chelsea Boots. Color Black Waterproof/Black/Black. $259.95.

Black Cole Haan Judson Grand Chelsea Boots

Black Cole Haan Judson Grand Chelsea Boots

+2

Brand Name: Cole Haan
Product Name: Judson Grand Chelsea Boots
Gender: Men's
Color: Black Waterproof/Black/Black
Price: $259.95
Rating

Helly Hansen - Garibaldi V3. Color Tobacco Brown/Espresso/Natural. Low Stock. $175.00. 4.0 out of 5 stars

Low Stock

Brown Helly Hansen Garibaldi V3

Brown Helly Hansen Garibaldi V3

+2

Brand Name: Helly Hansen
Product Name: Garibaldi V3
Gender: Men's
Color: Tobacco Brown/Espresso/Natural
Price: $175
Rating: 4Rated 4 stars out of 5(167)

ECCO - London Double Gore Chelsea Boots. Color Black. Low Stock. On sale for $224.95. MSRP $249.95. 10% off. 5.0 out of 5 stars

Low Stock

Black ECCO London Double Gore Chelsea Boots

Black ECCO London Double Gore Chelsea Boots

+2

Brand Name: ECCO
Product Name: London Double Gore Chelsea Boots
Gender: Men's
Color: Black
Price: $224.95MSRP: $249.9510% OFF
Rating: 5Rated 5 stars out of 5(2)

Hoka - Kaha 3 GTX®. Color Sea Moss/Oat Milk. $240.00. 3.6 out of 5 stars

Khaki Hoka Kaha 3 GTX®

Khaki Hoka Kaha 3 GTX®

+2

Brand Name: Hoka
Product Name: Kaha 3 GTX®
Gender: Men's
Color: Sea Moss/Oat Milk
Price: $240
Rating: 4Rated 4 stars out of 5(25)

Frye - Austin Inside Zip. Color Cognac. $388.00. 3.4 out of 5 stars

Tan Frye Austin Inside Zip

Tan Frye Austin Inside Zip

+3

Brand Name: Frye
Product Name: Austin Inside Zip
Gender: Men's
Color: Cognac
Price: $388
Rating: 3Rated 3 stars out of 5(39)

Red Wing Heritage - Blacksmith. Color Copper Rough & Tough. $329.99. 4.5 out of 5 stars

Tan Red Wing Heritage Blacksmith

Tan Red Wing Heritage Blacksmith

+2

Brand Name: Red Wing Heritage
Product Name: Blacksmith
Gender: Men's
Color: Copper Rough & Tough
Price: $329.99
Rating: 5Rated 5 stars out of 5(24)

Johnston & Murphy - Upton Chelsea Boots. Color Tan Full Grain. On sale for $119.99. MSRP $179.00. 33% off. 2.0 out of 5 stars

Tan Johnston & Murphy Upton Chelsea Boots

Tan Johnston & Murphy Upton Chelsea Boots

+2

Brand Name: Johnston & Murphy
Product Name: Upton Chelsea Boots
Gender: Men's
Color: Tan Full Grain
Price: $119.99MSRP: $17933% OFF
Rating: 2Rated 2 stars out of 5(1)

L.L.Bean - Bucksport Work Boot Plain Toe Waterproof. Color Coffee Bean. Low Stock. $199.00.

Low Stock

Brown L.L.Bean Bucksport Work Boot Plain Toe Waterproof

Brown L.L.Bean Bucksport Work Boot Plain Toe Waterproof

+2

Brand Name: L.L.Bean
Product Name: Bucksport Work Boot Plain Toe Waterproof
Gender: Men's
Color: Coffee Bean
Price: $199
Rating

Kenneth Cole - Raymond. Color Mocha Multi. On sale for $134.99. MSRP $184.95. 27% off.

Brown Kenneth Cole Raymond

Brown Kenneth Cole Raymond

+2

Brand Name: Kenneth Cole
Product Name: Raymond
Gender: Men's
Color: Mocha Multi
Price: $134.99MSRP: $184.9527% OFF
Rating

Columbia - Bugaboot III. Color Black/Bright Red 1. On sale for $94.00. MSRP $120.00. 22% off. 4.1 out of 5 stars

Black Columbia Bugaboot III

Black Columbia Bugaboot III

Brand Name: Columbia
Product Name: Bugaboot III
Gender: Men's
Color: Black/Bright Red 1
Price: $94MSRP: $12022% OFF
Rating: 4Rated 4 stars out of 5(370)

Cole Haan - Hawthorne Chelsea Boots. Color British Tan. On sale for $117.60. MSRP $168.00. 30% off. 5.0 out of 5 stars

Tan Cole Haan Hawthorne Chelsea Boots

Tan Cole Haan Hawthorne Chelsea Boots

+2

Brand Name: Cole Haan
Product Name: Hawthorne Chelsea Boots
Gender: Men's
Color: British Tan
Price: $117.60MSRP: $16830% OFF
Rating: 5Rated 5 stars out of 5(3)

Sperry - Tour Mid Moc. Color Dark Brown. Low Stock. On sale for $98.00. MSRP $140.00. 30% off.

Low Stock

Brown Sperry Tour Mid Moc

Brown Sperry Tour Mid Moc

Brand Name: Sperry
Product Name: Tour Mid Moc
Gender: Men's
Color: Dark Brown
Price: $98MSRP: $14030% OFF
Rating

Cole Haan - Muir Moc Tall Boots. Color Raven Suede/Raven Waterproof. On sale for $145.60. MSRP $208.00. 30% off. 5.0 out of 5 stars

Black Cole Haan Muir Moc Tall Boots

Black Cole Haan Muir Moc Tall Boots

+2

Brand Name: Cole Haan
Product Name: Muir Moc Tall Boots
Gender: Men's
Color: Raven Suede/Raven Waterproof
Price: $145.60MSRP: $20830% OFF
Rating: 5Rated 5 stars out of 5(1)

BRUNT - The Bolduc Comp Toe. Color Brown 1. $164.99. 3.5 out of 5 stars

Brown BRUNT The Bolduc Comp Toe

Brown BRUNT The Bolduc Comp Toe

+2

Brand Name: BRUNT
Product Name: The Bolduc Comp Toe
Gender: Men's
Color: Brown 1
Price: $164.99
Rating: 3Rated 3 stars out of 5(11)

Orthofeet - Highline. Color Black. $149.95. 5.0 out of 5 stars

Black Orthofeet Highline

Black Orthofeet Highline

Brand Name: Orthofeet
Product Name: Highline
Gender: Men's
Color: Black
Price: $149.95
Rating: 5Rated 5 stars out of 5(4)

Cole Haan - Originalgrand Remastered Waterproof Chukka Boots. Color Black/Black. On sale for $140.00. MSRP $200.00. 30% off. 2.2 out of 5 stars

Black Cole Haan Originalgrand Remastered Waterproof Chukka Boots

Black Cole Haan Originalgrand Remastered Waterproof Chukka Boots

+2

Brand Name: Cole Haan
Product Name: Originalgrand Remastered Waterproof Chukka Boots
Gender: Men's
Color: Black/Black
Price: $140MSRP: $20030% OFF
Rating: 2Rated 2 stars out of 5(4)

KEEN Utility - San Jose 6" (Soft Toe). Color Gingerbread/Off-White. $159.95. 4.1 out of 5 stars

Brown KEEN Utility San Jose 6" (Soft Toe)

Brown KEEN Utility San Jose 6" (Soft Toe)

+2

Brand Name: KEEN Utility
Product Name: San Jose 6" (Soft Toe)
Gender: Men's
Color: Gingerbread/Off-White
Price: $159.95
Rating: 4Rated 4 stars out of 5(126)

Johnston & Murphy - XC Flex Raleigh Chelsea. Color Tan Full Grain. Low Stock. On sale for $129.50. MSRP $185.00. 30% off. 4.4 out of 5 stars

Low Stock

Tan Johnston & Murphy XC Flex Raleigh Chelsea

Tan Johnston & Murphy XC Flex Raleigh Chelsea

Brand Name: Johnston & Murphy
Product Name: XC Flex Raleigh Chelsea
Gender: Men's
Color: Tan Full Grain
Price: $129.50MSRP: $18530% OFF
Rating: 4Rated 4 stars out of 5(69)

Steve Madden - Rydder. Color Brown. Low Stock. On sale for $80.69. MSRP $110.00. 27% off. 4.0 out of 5 stars

Low Stock

Brown Steve Madden Rydder

Brown Steve Madden Rydder

Brand Name: Steve Madden
Product Name: Rydder
Gender: Men's
Color: Brown
Price: $80.69MSRP: $11027% OFF
Rating: 4Rated 4 stars out of 5(2)

Deer Stags - Bangor. Color Black/Black. On sale for $58.62. MSRP $90.00. 35% off. 3.9 out of 5 stars

Black Deer Stags Bangor

Black Deer Stags Bangor

Brand Name: Deer Stags
Product Name: Bangor
Gender: Men's
Color: Black/Black
Price: $58.62MSRP: $9035% OFF
Rating: 4Rated 4 stars out of 5(14)

Stacy Adams - Bradley Chelsea Boot. Color Black. On sale for $119.90. MSRP $160.00. 25% off. 4.4 out of 5 stars

Black Stacy Adams Bradley Chelsea Boot

Black Stacy Adams Bradley Chelsea Boot

Brand Name: Stacy Adams
Product Name: Bradley Chelsea Boot
Gender: Men's
Color: Black
Price: $119.90MSRP: $16025% OFF
Rating: 4Rated 4 stars out of 5(7)

Caterpillar - Threshold Waterproof Steel Toe. Color Brown. $119.95. 4.1 out of 5 stars

Brown Caterpillar Threshold Waterproof Steel Toe

Brown Caterpillar Threshold Waterproof Steel Toe

Brand Name: Caterpillar
Product Name: Threshold Waterproof Steel Toe
Gender: Men's
Color: Brown
Price: $119.95
Rating: 4Rated 4 stars out of 5(74)

Deer Stags - Brayden. Color Black. $100.00. 3.3 out of 5 stars

Black Deer Stags Brayden

Black Deer Stags Brayden

Brand Name: Deer Stags
Product Name: Brayden
Gender: Men's
Color: Black
Price: $100
Rating: 3Rated 3 stars out of 5(3)

Columbia - Navigator Trek Outdry Leather. Color Cordovan/Canyon Sun. Low Stock. $200.00.

Low Stock

Brown Columbia Navigator Trek Outdry Leather

Brown Columbia Navigator Trek Outdry Leather

+2 colors/patterns

Brand Name: Columbia
Product Name: Navigator Trek Outdry Leather
Gender: Men's
Color: Cordovan/Canyon Sun
Price: $200
Rating

. Carhartt - Millbrook 4" Romeo Soft Toe Wedge Boots. Color Black Oil Tanned. $144.99. 3.5 out of 5 stars

Black Carhartt Millbrook 4" Romeo Soft Toe Wedge Boots

Black Carhartt Millbrook 4" Romeo Soft Toe Wedge Boots

+2

Brand Name: Carhartt
Product Name: Millbrook 4" Romeo Soft Toe Wedge Boots
Gender: Men's
Color: Black Oil Tanned
Price: $144.99
Rating: 3Rated 3 stars out of 5(59)

Roper - Monterey. Color Black. Low Stock. $124.99. 4.8 out of 5 stars

Low Stock

Black Roper Monterey

Black Roper Monterey

Brand Name: Roper
Product Name: Monterey
Gender: Men's
Color: Black
Price: $124.99
Rating: 5Rated 5 stars out of 5(5)

KEEN Utility - Cincinnati 6" Waterproof (Soft Toe). Color Belgian/Sandshell. $190.00. 4.0 out of 5 stars

Brown KEEN Utility Cincinnati 6" Waterproof (Soft Toe)

Brown KEEN Utility Cincinnati 6" Waterproof (Soft Toe)

Brand Name: KEEN Utility
Product Name: Cincinnati 6" Waterproof (Soft Toe)
Gender: Men's
Color: Belgian/Sandshell
Price: $190
Rating: 4Rated 4 stars out of 5(187)

Steve Madden - Duke. Color Cognac Leather. On sale for $98.00. MSRP $140.00. 30% off. 5.0 out of 5 stars

Brown Steve Madden Duke

Brown Steve Madden Duke

+2

Brand Name: Steve Madden
Product Name: Duke
Gender: Men's
Color: Cognac Leather
Price: $98MSRP: $14030% OFF
Rating: 5Rated 5 stars out of 5(1)

KEEN Utility - San Jose 6” Alloy Toe Waterproof 90 Degree Heel. Color Bison/Black. $180.00. 3.0 out of 5 stars

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

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

+2

Brand Name: KEEN Utility
Product Name: San Jose 6” Alloy Toe Waterproof 90 Degree Heel
Gender: Men's
Color: Bison/Black
Price: $180
Rating: 3Rated 3 stars out of 5(12)

Marc Joseph New York - Austin. Color Cognac Grainy. On sale for $89.95. MSRP $195.00. 54% off. 4.1 out of 5 stars

Brown Marc Joseph New York Austin

Brown Marc Joseph New York Austin

Brand Name: Marc Joseph New York
Product Name: Austin
Gender: Men's
Color: Cognac Grainy
Price: $89.95MSRP: $19554% OFF
Rating: 4Rated 4 stars out of 5(9)

Timberland PRO - Boondock 8" Composite Toe. Color Brown 3. $219.95. 4.3 out of 5 stars

Brown Timberland PRO Boondock 8" Composite Toe

Brown Timberland PRO Boondock 8" Composite Toe

+2

Brand Name: Timberland PRO
Product Name: Boondock 8" Composite Toe
Gender: Men's
Color: Brown 3
Price: $219.95
Rating: 4Rated 4 stars out of 5(587)

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

Gray Propet Veymont

Gray Propet Veymont

Brand Name: Propet
Product Name: Veymont
Gender: Men's
Color: Grey/Blue
Price: $128MSRP: $169.9525% OFF
Rating: 3Rated 3 stars out of 5(15)

Carhartt - Force 5" Lightweight Sneaker Boots Nano Comp Toe. Color Black Textile. $144.99. 4.0 out of 5 stars

Black Carhartt Force 5" Lightweight Sneaker Boots Nano Comp Toe

Black Carhartt Force 5" Lightweight Sneaker Boots Nano Comp Toe

Brand Name: Carhartt
Product Name: Force 5" Lightweight Sneaker Boots Nano Comp Toe
Gender: Men's
Color: Black Textile
Price: $144.99
Rating: 4Rated 4 stars out of 5(188)

Caterpillar - Outline ST. Color Honey Reset. $109.95. 3.5 out of 5 stars

Beige Caterpillar Outline ST

Beige Caterpillar Outline ST

+2

Brand Name: Caterpillar
Product Name: Outline ST
Gender: Men's
Color: Honey Reset
Price: $109.95
Rating: 4Rated 4 stars out of 5(30)

Allen Edmonds - Park Boot. Color Chili. Low Stock. On sale for $330.00. MSRP $550.00. 40% off. 3.9 out of 5 stars

Low Stock

Brown Allen Edmonds Park Boot

Brown Allen Edmonds Park Boot

+2

Brand Name: Allen Edmonds
Product Name: Park Boot
Gender: Men's
Color: Chili
Price: $330MSRP: $55040% OFF
Rating: 4Rated 4 stars out of 5(15)

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