GOING FAST
EXTRA 20% OFF*
Save on select styles with code EXTRA20
Shop Now
*Exclusions apply

Skip to search results Skip to filters Skip to sort Skip to selected filters

Men's Size 8.5 Ankle Comfort Products

433 items found

Filters

Search Results

SOREL - Outing Nw Sneaker Mid Waterproof. Color Khaki Ii/Jet. On sale for $89.96. MSRP $120.00. 25% off. 4.3 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(7)

Clarks - Shepton Easy. Color Beeswax Leather. On sale for $101.50. MSRP $130.00. 22% off. 5.0 out of 5 stars

Brown Clarks Shepton Easy

Brown Clarks Shepton Easy

+2

Brand Name: Clarks
Product Name: Shepton Easy
Gender: Men's
Color: Beeswax Leather
Price: $101.50MSRP: $13022% OFF
Rating: 5Rated 5 stars out of 5(1)

Orthofeet - Granite. Color Black. $164.95. 4.1 out of 5 stars

Black Orthofeet Granite

Black Orthofeet Granite

+2

Brand Name: Orthofeet
Product Name: Granite
Gender: Men's
Color: Black
Price: $164.95
Rating: 4Rated 4 stars out of 5(42)

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

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)

SOREL - Slabtown 62'™ Moc Waterproof. Color Velvet Tan/Tobacco. On sale for $108.00. MSRP $180.00. 40% off. 4.1 out of 5 stars

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: $108MSRP: $18040% OFF
Rating: 4Rated 4 stars out of 5(33)

Florsheim - Forge Plain Toe Gore Boots. Color Black. $130.00. 4.1 out of 5 stars

Black Florsheim Forge Plain Toe Gore Boots

Black Florsheim Forge Plain Toe Gore Boots

+3

Brand Name: Florsheim
Product Name: Forge Plain Toe Gore Boots
Gender: Men's
Color: Black
Price: $130
Rating: 4Rated 4 stars out of 5(29)

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

+3

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

UGG - Idyllwild Lace. Color Black/Black. $189.95. 4.8 out of 5 stars

Black UGG Idyllwild Lace

Black UGG Idyllwild Lace

+2

Brand Name: UGG
Product Name: Idyllwild Lace
Gender: Men's
Color: Black/Black
Price: $189.95
Rating: 5Rated 5 stars out of 5(4)

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

Sperry - Mini Lug Chukka. Color Other Beige. On sale for $148.04. MSRP $150.00. 1% off.

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: $148.04MSRP: $1501% OFF
Rating

ECCO - Metropole Milan Chukka Boots. Color Camel Suede. On sale for $142.59. MSRP $194.95. 27% 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: $142.59MSRP: $194.9527% OFF
Rating: 4Rated 4 stars out of 5(1)

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)

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(18)

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)

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

Columbia - Burnsider Omni-Heat Infinity. Color Dark Brown/Dark Mountain. Low Stock. On sale for $126.88. MSRP $130.00. 2% off.

Low Stock

Brown Columbia Burnsider Omni-Heat Infinity

Brown Columbia Burnsider Omni-Heat Infinity

+2

Brand Name: Columbia
Product Name: Burnsider Omni-Heat Infinity
Gender: Men's
Color: Dark Brown/Dark Mountain
Price: $126.88MSRP: $1302% OFF
Rating

Stacy Adams - Brumley Moc Toe Lace-Up Boots. Color Brown Multi. On sale for $114.99. MSRP $160.00. 28% off.

Black Stacy Adams Brumley Moc Toe Lace-Up Boots

Black Stacy Adams Brumley Moc Toe Lace-Up Boots

+2 colors/patterns

Brand Name: Stacy Adams
Product Name: Brumley Moc Toe Lace-Up Boots
Gender: Men's
Color: Brown Multi
Price: $114.99MSRP: $16028% OFF
Rating

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)

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

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)

Rockport - Evan Waterproof Boots. Color Dark Brown Multi. $149.95. 3.5 out of 5 stars

Brown Rockport Evan Waterproof Boots

Brown Rockport Evan Waterproof Boots

Brand Name: Rockport
Product Name: Evan Waterproof Boots
Gender: Men's
Color: Dark Brown Multi
Price: $149.95
Rating: 4Rated 4 stars out of 5(2)

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)

Columbia - Expeditionist Peak Ox. Color Stratus/Graphite. Low Stock. On sale for $171.00. MSRP $190.00. 10% 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: $171MSRP: $19010% OFF
Rating: 5Rated 5 stars out of 5(1)

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

Rockport - Seamus. Color Grey Suede. On sale for $89.98. MSRP $149.95. 40% off. 1.0 out of 5 stars

Gray Rockport Seamus

Gray Rockport Seamus

Brand Name: Rockport
Product Name: Seamus
Gender: Men's
Color: Grey Suede
Price: $89.98MSRP: $149.9540% OFF
Rating: 1Rated 1 star out of 5(1)

Eastland 1955 Edition - Jack. Color Peanut. Low Stock. On sale for $119.99. MSRP $125.00. 4% off. 4.4 out of 5 stars

Low Stock

Brown Eastland 1955 Edition Jack

Brown Eastland 1955 Edition Jack

+1

Brand Name: Eastland 1955 Edition
Product Name: Jack
Gender: Men's
Color: Peanut
Price: $119.99MSRP: $1254% OFF
Rating: 4Rated 4 stars out of 5(10)

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

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)

Scarpa - Moraine Mid WP. Color Anthracite 1. $189.00. 4.0 out of 5 stars

Silver Scarpa Moraine Mid WP

Silver Scarpa Moraine Mid WP

+2 colors/patterns

Brand Name: Scarpa
Product Name: Moraine Mid WP
Gender: Men's
Color: Anthracite 1
Price: $189
Rating: 4Rated 4 stars out of 5(1)

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)

Zamberlan - Thunder GTX. Color Brown/Sand. $350.00.

Brown Zamberlan Thunder GTX

Brown Zamberlan Thunder GTX

Brand Name: Zamberlan
Product Name: Thunder GTX
Gender: Men's
Color: Brown/Sand
Price: $350
Rating

Johnston & Murphy - Dudley Lug Wingtip Boots. Color Navy Multi Hand-stained Calfskin. $325.00. 3.0 out of 5 stars

Black Johnston & Murphy Dudley Lug Wingtip Boots

Black Johnston & Murphy Dudley Lug Wingtip Boots

Brand Name: Johnston & Murphy
Product Name: Dudley Lug Wingtip Boots
Gender: Men's
Color: Navy Multi Hand-stained Calfskin
Price: $325
Rating: 3Rated 3 stars out of 5(1)

Propet - Veymont. Color Grey/Blue. On sale for $108.80. MSRP $169.95. 36% 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: $108.80MSRP: $169.9536% OFF
Rating: 3Rated 3 stars out of 5(15)

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(582)

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)

5 of 5

1 2 3 45Next Page

Join Our Email List

Never miss out on latest drops & sales—plus, new subscribers get 10% off.*

*One code per email address.