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Size 8.5 Medium Size Ankle Comfort On Sale Products

148 items found

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Cole Haan - American Classics Chelsea Boots. Color Morel Nubuck Waterproof/Black. On sale for $140.00. MSRP $200.00. 30% off. 3.0 out of 5 stars

Taupe Cole Haan American Classics Chelsea Boots

Taupe Cole Haan American Classics Chelsea Boots

+2

Brand Name: Cole Haan
Product Name: American Classics Chelsea Boots
Gender: Men's
Color: Morel Nubuck Waterproof/Black
Price: $140MSRP: $20030% OFF
Rating: 3Rated 3 stars out of 5(1)

. Timberland PRO - Sawhorse 6" Composite Safety Toe. Color Black 1. On sale for $129.95. MSRP $150.00. 13% off. 3.4 out of 5 stars

Black Timberland PRO Sawhorse 6" Composite Safety Toe

Black Timberland PRO Sawhorse 6" Composite Safety Toe

+5

Brand Name: Timberland PRO
Product Name: Sawhorse 6" Composite Safety Toe
Gender: Unisex
Color: Black 1
Price: $129.95MSRP: $15013% OFF
Rating: 3Rated 3 stars out of 5(1548)

Clarks - Shepton. Color Dark Brown Leather. On sale for $88.00. MSRP $110.00. 20% off. 1.6 out of 5 stars

Brown Clarks Shepton

Brown Clarks Shepton

+6

Brand Name: Clarks
Product Name: Shepton
Gender: Men's
Color: Dark Brown Leather
Price: $88MSRP: $11020% OFF
Rating: 2Rated 2 stars out of 5(7)

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

Neutral Frye Paul Chukka

Neutral Frye Paul Chukka

+2

Brand Name: Frye
Product Name: Paul Chukka
Gender: Men's
Color: Mushroom
Price: $169.20MSRP: $18810% OFF
Rating: 4Rated 4 stars out of 5(9)

Born - Ryker. Color Brown (Wood). On sale for $90.00. MSRP $150.00. 40% off. 1.0 out of 5 stars

Brown Born Ryker

Brown Born Ryker

+2

Brand Name: Born
Product Name: Ryker
Gender: Men's
Color: Brown (Wood)
Price: $90MSRP: $15040% OFF
Rating: 1Rated 1 star out of 5(2)

Birkenstock - Highwood Deep Blue. Color Dark Tea. On sale for $105.00. MSRP $210.00. 50% off. 4.2 out of 5 stars

Beige Birkenstock Highwood Deep Blue

Beige Birkenstock Highwood Deep Blue

+4

Brand Name: Birkenstock
Product Name: Highwood Deep Blue
Gender: Men's
Color: Dark Tea
Price: $105MSRP: $21050% OFF
Rating: 4Rated 4 stars out of 5(9)

Stacy Adams - Eastmont Elastic Lace Boots. Color White. Low Stock. On sale for $77.00. MSRP $140.00. 45% off. 4.5 out of 5 stars

Low Stock

White Stacy Adams Eastmont Elastic Lace Boots

White Stacy Adams Eastmont Elastic Lace Boots

+2

Brand Name: Stacy Adams
Product Name: Eastmont Elastic Lace Boots
Gender: Men's
Color: White
Price: $77MSRP: $14045% OFF
Rating: 5Rated 5 stars out of 5(2)

Dockers - Dylan. Color Black. On sale for $85.50. MSRP $95.00. 10% off. 3.0 out of 5 stars

Black Dockers Dylan

Black Dockers Dylan

+3

Brand Name: Dockers
Product Name: Dylan
Gender: Men's
Color: Black
Price: $85.50MSRP: $9510% OFF
Rating: 3Rated 3 stars out of 5(2)

Johnston & Murphy - Upton Chukka. Color Tan Oiled Full Grain. On sale for $119.99. MSRP $179.00. 33% off. 4.1 out of 5 stars

Tan Johnston & Murphy Upton Chukka

Tan Johnston & Murphy Upton Chukka

+4

Brand Name: Johnston & Murphy
Product Name: Upton Chukka
Gender: Men's
Color: Tan Oiled Full Grain
Price: $119.99MSRP: $17933% OFF
Rating: 4Rated 4 stars out of 5(265)

Allen Edmonds - Tanner. Color Bitter Chocolate. On sale for $385.00. MSRP $550.00. 30% off.

Brown Allen Edmonds Tanner

Brown Allen Edmonds Tanner

+3

Brand Name: Allen Edmonds
Product Name: Tanner
Gender: Men's
Color: Bitter Chocolate
Price: $385MSRP: $55030% OFF
Rating

. Columbia - Newton Wander. Color Black/Black. On sale for $99.00. MSRP $110.00. 10% off. 4.5 out of 5 stars

Black Columbia Newton Wander

Black Columbia Newton Wander

+6

Brand Name: Columbia
Product Name: Newton Wander
Gender: Men's
Color: Black/Black
Price: $99MSRP: $11010% OFF
Rating: 5Rated 5 stars out of 5(4)

Nunn Bush - Chase Plain Toe Chukka Contemporary Fashion Boot. Color Black. On sale for $64.95. MSRP $95.00. 32% off. 3.9 out of 5 stars

Black Nunn Bush Chase Plain Toe Chukka Contemporary Fashion Boot

Black Nunn Bush Chase Plain Toe Chukka Contemporary Fashion Boot

+3

Brand Name: Nunn Bush
Product Name: Chase Plain Toe Chukka Contemporary Fashion Boot
Gender: Men's
Color: Black
Price: $64.95MSRP: $9532% OFF
Rating: 4Rated 4 stars out of 5(18)

Merrell - Moab Adventure 3 Chelsea Wp. Color Black. On sale for $126.99. MSRP $170.00. 25% off. 2.9 out of 5 stars

Black Merrell Moab Adventure 3 Chelsea Wp

Black Merrell Moab Adventure 3 Chelsea Wp

+2

Brand Name: Merrell
Product Name: Moab Adventure 3 Chelsea Wp
Gender: Men's
Color: Black
Price: $126.99MSRP: $17025% OFF
Rating: 3Rated 3 stars out of 5(9)

Rockport - Storm Surge Water Proof Plain Toe Boots. Color Tan. On sale for $119.95. MSRP $159.95. 25% off. 3.3 out of 5 stars

Tan Rockport Storm Surge Water Proof Plain Toe Boots

Tan Rockport Storm Surge Water Proof Plain Toe Boots

+2

Brand Name: Rockport
Product Name: Storm Surge Water Proof Plain Toe Boots
Gender: Men's
Color: Tan
Price: $119.95MSRP: $159.9525% OFF
Rating: 3Rated 3 stars out of 5(19)

Propet - Blizzard Ankle Zip. Color Brown/Black. On sale for $119.95. MSRP $139.99. 14% off. 4.3 out of 5 stars

Brown Propet Blizzard Ankle Zip

Brown Propet Blizzard Ankle Zip

+2

Brand Name: Propet
Product Name: Blizzard Ankle Zip
Gender: Men's
Color: Brown/Black
Price: $119.95MSRP: $139.9914% OFF
Rating: 4Rated 4 stars out of 5(144)

Deer Stags - Garfield. Color Dark Brown. On sale for $64.97. MSRP $100.00. 35% off. 2.0 out of 5 stars

Brown Deer Stags Garfield

Brown Deer Stags Garfield

+3

Brand Name: Deer Stags
Product Name: Garfield
Gender: Men's
Color: Dark Brown
Price: $64.97MSRP: $10035% OFF
Rating: 2Rated 2 stars out of 5(2)

Florsheim - Norwalk Side Zip Boots. Color Black Crazy Horse. On sale for $120.00. MSRP $165.00. 27% off. 4.5 out of 5 stars

Black Florsheim Norwalk Side Zip Boots

Black Florsheim Norwalk Side Zip Boots

+2

Brand Name: Florsheim
Product Name: Norwalk Side Zip Boots
Gender: Men's
Color: Black Crazy Horse
Price: $120MSRP: $16527% OFF
Rating: 5Rated 5 stars out of 5(138)

Orthofeet - Graphite. Color Black. On sale for $107.99. MSRP $179.99. 40% off. 3.0 out of 5 stars

Black Orthofeet Graphite

Black Orthofeet Graphite

+2

Brand Name: Orthofeet
Product Name: Graphite
Gender: Men's
Color: Black
Price: $107.99MSRP: $179.9940% OFF
Rating: 3Rated 3 stars out of 5(1)

SOREL - Outing Nw Sneaker Mid Waterproof. Color Khaki Ii/Jet. On sale for $89.96. MSRP $120.00. 25% off. 4.1 out of 5 stars

Khaki SOREL Outing Nw Sneaker Mid Waterproof

Khaki SOREL Outing Nw Sneaker Mid Waterproof

+3

Brand Name: SOREL
Product Name: Outing Nw Sneaker Mid Waterproof
Gender: Men's
Color: Khaki Ii/Jet
Price: $89.96MSRP: $12025% OFF
Rating: 4Rated 4 stars out of 5(8)

Vance - Rogue. Color Wheat. On sale for $71.99. MSRP $89.99. 20% off.

Tan Vance Rogue

Tan Vance Rogue

+3

Brand Name: Vance
Product Name: Rogue
Gender: Men's
Color: Wheat
Price: $71.99MSRP: $89.9920% OFF
Rating

SOREL - Slabtown 62'™ Moc Waterproof. Color Velvet Tan/Tobacco. Low Stock. On sale for $108.16. MSRP $180.00. 40% off. 4.1 out of 5 stars

Low Stock

Brown SOREL Slabtown 62'™ Moc Waterproof

Brown SOREL Slabtown 62'™ Moc Waterproof

+2

Brand Name: SOREL
Product Name: Slabtown 62'™ Moc Waterproof
Gender: Men's
Color: Velvet Tan/Tobacco
Price: $108.16MSRP: $18040% OFF
Rating: 4Rated 4 stars out of 5(33)

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

Dunham - Brisco. Color Black Leather. On sale for $117.95. MSRP $159.95. 26% 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: $117.95MSRP: $159.9526% OFF
Rating: 4Rated 4 stars out of 5(1)

Dansko - Tony. Color Black. On sale for $114.98. MSRP $194.95. 41% off.

Black Dansko Tony

Black Dansko Tony

+2

Brand Name: Dansko
Product Name: Tony
Gender: Men's
Color: Black
Price: $114.98MSRP: $194.9541% OFF
Rating

Florsheim - Rucci Wingtip Lace Boots. Color Black. On sale for $128.99. MSRP $155.00. 17% off. 4.9 out of 5 stars

Black Florsheim Rucci Wingtip Lace Boots

Black Florsheim Rucci Wingtip Lace Boots

+2

Brand Name: Florsheim
Product Name: Rucci Wingtip Lace Boots
Gender: Men's
Color: Black
Price: $128.99MSRP: $15517% OFF
Rating: 5Rated 5 stars out of 5(30)

Cole Haan - Chamberlin Grand Cap Toe Boots. Color Spiced Brown Suede/Water Resistant. On sale for $94.00. MSRP $150.00. 37% off.

Brown Cole Haan Chamberlin Grand Cap Toe Boots

Brown Cole Haan Chamberlin Grand Cap Toe Boots

+2

Brand Name: Cole Haan
Product Name: Chamberlin Grand Cap Toe Boots
Gender: Men's
Color: Spiced Brown Suede/Water Resistant
Price: $94MSRP: $15037% OFF
Rating

Steve Madden - Mtrenter. Color Brown. Low Stock. On sale for $62.99. MSRP $89.99. 30% off. 5.0 out of 5 stars

Low Stock

Brown Steve Madden Mtrenter

Brown Steve Madden Mtrenter

+2

Brand Name: Steve Madden
Product Name: Mtrenter
Gender: Men's
Color: Brown
Price: $62.99MSRP: $89.9930% OFF
Rating: 5Rated 5 stars out of 5(1)

ECCO - Metropole Milan Chukka Boots. Color Camel Suede. On sale for $155.41. MSRP $194.95. 20% 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: $155.41MSRP: $194.9520% OFF
Rating: 4Rated 4 stars out of 5(1)

Wolverine - Carlsbad Cap-Toe 6". Color Brown. On sale for $94.95. MSRP $115.00. 17% off.

Brown Wolverine Carlsbad Cap-Toe 6"

Brown Wolverine Carlsbad Cap-Toe 6"

Brand Name: Wolverine
Product Name: Carlsbad Cap-Toe 6"
Gender: Men's
Color: Brown
Price: $94.95MSRP: $11517% OFF
Rating

Stacy Adams - Platt Chelsea Boots. Color Black. On sale for $89.99. MSRP $110.00. 18% off.

Black Stacy Adams Platt Chelsea Boots

Black Stacy Adams Platt Chelsea Boots

+2

Brand Name: Stacy Adams
Product Name: Platt Chelsea Boots
Gender: Men's
Color: Black
Price: $89.99MSRP: $11018% OFF
Rating

Columbia - Bugaboot III. Color Black/Bright Red 1. On sale for $104.98. MSRP $120.00. 13% 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: $104.98MSRP: $12013% OFF
Rating: 4Rated 4 stars out of 5(370)

Eastland 1955 Edition - Chimney Pond. Color Black. Low Stock. On sale for $87.00. MSRP $145.00. 40% off. 5.0 out of 5 stars

Low Stock

Black Eastland 1955 Edition Chimney Pond

Black Eastland 1955 Edition Chimney Pond

+2

Brand Name: Eastland 1955 Edition
Product Name: Chimney Pond
Gender: Men's
Color: Black
Price: $87MSRP: $14540% OFF
Rating: 5Rated 5 stars out of 5(2)

Vance - Zeus. Color Black. On sale for $62.99. MSRP $89.99. 30% off.

Black Vance Zeus

Black Vance Zeus

+2

Brand Name: Vance
Product Name: Zeus
Gender: Men's
Color: Black
Price: $62.99MSRP: $89.9930% OFF
Rating

Clarks - Eastridge Mid. Color Beeswax Leather. On sale for $89.99. MSRP $120.00. 25% off. 2.0 out of 5 stars

Brown Clarks Eastridge Mid

Brown Clarks Eastridge Mid

+2

Brand Name: Clarks
Product Name: Eastridge Mid
Gender: Men's
Color: Beeswax Leather
Price: $89.99MSRP: $12025% OFF
Rating: 2Rated 2 stars out of 5(2)

Johnston & Murphy - Connelly Wing Tip Boot. Color Tan Full Grain. Low Stock. On sale for $139.99. MSRP $219.00. 36% off. 3.2 out of 5 stars

Low Stock

Tan Johnston & Murphy Connelly Wing Tip Boot

Tan Johnston & Murphy Connelly Wing Tip Boot

Brand Name: Johnston & Murphy
Product Name: Connelly Wing Tip Boot
Gender: Men's
Color: Tan Full Grain
Price: $139.99MSRP: $21936% OFF
Rating: 3Rated 3 stars out of 5(58)

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)

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

+3

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)

Columbia - Expeditionist Peak Ox. Color Stratus/Graphite. Low Stock. On sale for $152.00. MSRP $190.00. 20% off. 5.0 out of 5 stars

Low Stock

Gray Columbia Expeditionist Peak Ox

Gray Columbia Expeditionist Peak Ox

Brand Name: Columbia
Product Name: Expeditionist Peak Ox
Gender: Men's
Color: Stratus/Graphite
Price: $152MSRP: $19020% OFF
Rating: 5Rated 5 stars out of 5(1)

Stacy Adams - Bradley Chelsea Boot. Color Black. On sale for $119.90. MSRP $160.00. 25% off. 4.2 out of 5 stars

Black Stacy Adams Bradley Chelsea Boot

Black Stacy Adams Bradley Chelsea Boot

+2

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(5)

Tommy Hilfiger - Berton. Color Cognac. On sale for $59.50. MSRP $119.00. 50% off.

Tan Tommy Hilfiger Berton

Tan Tommy Hilfiger Berton

+2

Brand Name: Tommy Hilfiger
Product Name: Berton
Gender: Men's
Color: Cognac
Price: $59.50MSRP: $11950% OFF
Rating

Merrell - Wrapt Sneakers Mid Waterproof. Color Coffee. On sale for $99.99. MSRP $150.00. 33% off. 2.0 out of 5 stars

Brown Merrell Wrapt Sneakers Mid Waterproof

Brown Merrell Wrapt Sneakers Mid Waterproof

+2

Brand Name: Merrell
Product Name: Wrapt Sneakers Mid Waterproof
Gender: Men's
Color: Coffee
Price: $99.99MSRP: $15033% OFF
Rating: 2Rated 2 stars out of 5(1)

adidas - Terrex Trailmaker 2 Leather Hiking Shoes. Color Olive Strata/Olive Strata/Silver Pebble. On sale for $108.98. MSRP $130.00. 16% off. 4.5 out of 5 stars

Olive adidas Terrex Trailmaker 2 Leather Hiking Shoes

Olive 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: $108.98MSRP: $13016% OFF
Rating: 4Rated 4 stars out of 5(21)

Deer Stags - Bangor. Color Black/Black. On sale for $54.00. MSRP $90.00. 40% 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: $54MSRP: $9040% OFF
Rating: 4Rated 4 stars out of 5(14)

KEEN - KS Moc Chukka. Color Black/Black. On sale for $125.95. MSRP $139.95. 10% off.

Black KEEN KS Moc Chukka

Black KEEN KS Moc Chukka

Brand Name: KEEN
Product Name: KS Moc Chukka
Gender: Men's
Color: Black/Black
Price: $125.95MSRP: $139.9510% OFF
Rating

Allen Edmonds - Tompkins. Color Snuff Suede. On sale for $346.50. MSRP $495.00. 30% off. 3.5 out of 5 stars

Brown Allen Edmonds Tompkins

Brown Allen Edmonds Tompkins

+2

Brand Name: Allen Edmonds
Product Name: Tompkins
Gender: Men's
Color: Snuff Suede
Price: $346.50MSRP: $49530% OFF
Rating: 4Rated 4 stars out of 5(2)

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)

Timberland - Britton Road Mid Lace Up Waterproof. Color Wheat Full Grain. On sale for $93.50. MSRP $170.00. 45% off. 4.7 out of 5 stars

Brown Timberland Britton Road Mid Lace Up Waterproof

Brown Timberland Britton Road Mid Lace Up Waterproof

Brand Name: Timberland
Product Name: Britton Road Mid Lace Up Waterproof
Gender: Men's
Color: Wheat Full Grain
Price: $93.50MSRP: $17045% OFF
Rating: 5Rated 5 stars out of 5(60)

Allen Edmonds - Park Boot. Color Chili. Low Stock. On sale for $385.00. MSRP $550.00. 30% 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: $385MSRP: $55030% OFF
Rating: 4Rated 4 stars out of 5(15)

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