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

Size 8.5 Ankle Products

32 items found

Sort By

Your Selections

Search Results

Columbia - Newton Ridge Plus II Waterproof. Color Cordovan/Squash. On sale for $75.00. MSRP $100.00. 25% off. 4.4 out of 5 stars

Brown Columbia Newton Ridge Plus II Waterproof

Brown Columbia Newton Ridge Plus II Waterproof

+6

Brand Name: Columbia
Product Name: Newton Ridge Plus II Waterproof
Gender: Men's
Color: Cordovan/Squash
Price: $75.00MSRP: $100.0025% OFF
Rating: 4Rated 4 stars out of 5(1332)

Columbia - Crestwood Mid Waterproof. Color Cordovan/Squash 1. On sale for $68.99. MSRP $90.00. 23% off. 4.1 out of 5 stars

Taupe Columbia Crestwood Mid Waterproof

Taupe Columbia Crestwood Mid Waterproof

+4

Brand Name: Columbia
Product Name: Crestwood Mid Waterproof
Gender: Men's
Color: Cordovan/Squash 1
Price: $68.99MSRP: $90.0023% OFF
Rating: 4Rated 4 stars out of 5(203)

Columbia - Transverse™ Hike Waterproof. Color Cordovan/Golden Yellow. On sale for $60.00. MSRP $80.00. 25% off. 4.0 out of 5 stars

Brown Columbia Transverse™ Hike Waterproof

Brown Columbia Transverse™ Hike Waterproof

Brand Name: Columbia
Product Name: Transverse™ Hike Waterproof
Gender: Men's
Color: Cordovan/Golden Yellow
Price: $60.00MSRP: $80.0025% OFF
Rating: 4Rated 4 stars out of 5(112)

SKECHERS Work - Delson 3.0 SR - Tyoll Comp Toe. Color Grey. On sale for $55.07. MSRP $95.00. 42% off. 2.5 out of 5 stars

Gray SKECHERS Work Delson 3.0 SR - Tyoll Comp Toe

Gray SKECHERS Work Delson 3.0 SR - Tyoll Comp Toe

+3

Brand Name: SKECHERS Work
Product Name: Delson 3.0 SR - Tyoll Comp Toe
Gender: Men's
Color: Grey
Price: $55.07MSRP: $95.0042% OFF
Rating: 3Rated 3 stars out of 5(6)

Steve Madden - Montreaux. Color Tan. On sale for $87.10. MSRP $130.00. 33% off.

Tan Steve Madden Montreaux

Tan Steve Madden Montreaux

Brand Name: Steve Madden
Product Name: Montreaux
Gender: Men's
Color: Tan
Price: $87.10MSRP: $130.0033% OFF
Rating

L.L.Bean - Stonington Boots Moc Toe. Color Dark Oakwood. On sale for $96.00. MSRP $149.00. 36% off. 4.6 out of 5 stars

Brown L.L.Bean Stonington Boots Moc Toe

Brown L.L.Bean Stonington Boots Moc Toe

+2

Brand Name: L.L.Bean
Product Name: Stonington Boots Moc Toe
Gender: Men's
Color: Dark Oakwood
Price: $96.00MSRP: $149.0036% OFF
Rating: 5Rated 5 stars out of 5(397)

Eastland 1955 Edition - High Fidelity. Color Tan Leather. On sale for $81.00. MSRP $135.00. 40% off. 3.6 out of 5 stars

Tan Eastland 1955 Edition High Fidelity

Tan Eastland 1955 Edition High Fidelity

+5

Brand Name: Eastland 1955 Edition
Product Name: High Fidelity
Gender: Men's
Color: Tan Leather
Price: $81.00MSRP: $135.0040% OFF
Rating: 4Rated 4 stars out of 5(13)

Eastland 1955 Edition - Finn. Color Tan. On sale for $77.40. MSRP $90.00. 14% off.

Tan Eastland 1955 Edition Finn

Tan Eastland 1955 Edition Finn

+3

Brand Name: Eastland 1955 Edition
Product Name: Finn
Gender: Men's
Color: Tan
Price: $77.40MSRP: $90.0014% OFF
Rating

Columbia - Fairbanks Omni-Heat. Color Elk/Rusty 1. On sale for $93.75. MSRP $125.00. 25% off. 4.4 out of 5 stars

Brown Columbia Fairbanks Omni-Heat

Brown Columbia Fairbanks Omni-Heat

+4

Brand Name: Columbia
Product Name: Fairbanks Omni-Heat
Gender: Men's
Color: Elk/Rusty 1
Price: $93.75MSRP: $125.0025% OFF
Rating: 4Rated 4 stars out of 5(819)

Deer Stags - Bangor. Color Redwood/Dark Brown. On sale for $48.00. MSRP $100.00. 52% off. 3.9 out of 5 stars

Brown Deer Stags Bangor

Brown Deer Stags Bangor

+2

Brand Name: Deer Stags
Product Name: Bangor
Gender: Men's
Color: Redwood/Dark Brown
Price: $48.00MSRP: $100.0052% OFF
Rating: 4Rated 4 stars out of 5(14)

Tommy Hilfiger - Bage. Color Black Tumble. On sale for $76.16. MSRP $119.00. 36% off. 5.0 out of 5 stars

Black Tommy Hilfiger Bage

Black Tommy Hilfiger Bage

+3

Brand Name: Tommy Hilfiger
Product Name: Bage
Gender: Men's
Color: Black Tumble
Price: $76.16MSRP: $119.0036% OFF
Rating: 5Rated 5 stars out of 5(1)

Eastland 1955 Edition - Jason. Color Tan. $90.00.

Tan Eastland 1955 Edition Jason

Tan Eastland 1955 Edition Jason

+3

Brand Name: Eastland 1955 Edition
Product Name: Jason
Gender: Men's
Color: Tan
Price: $90.00
Rating

Propet - Cliff Walker. Color Wheat. On sale for $93.71. MSRP $124.95. 25% off. 3.9 out of 5 stars

Tan Propet Cliff Walker

Tan Propet Cliff Walker

Brand Name: Propet
Product Name: Cliff Walker
Gender: Men's
Color: Wheat
Price: $93.71MSRP: $124.9525% OFF
Rating: 4Rated 4 stars out of 5(8)

Columbia - Strata Trail™ Mid Wp. Color City Grey/Savory. On sale for $67.50. MSRP $90.00. 25% off.

Gray Columbia Strata Trail™ Mid Wp

Gray Columbia Strata Trail™ Mid Wp

+2

Brand Name: Columbia
Product Name: Strata Trail™ Mid Wp
Gender: Men's
Color: City Grey/Savory
Price: $67.50MSRP: $90.0025% OFF
Rating

Propet - Cliff Walker Tall Strap. Color Black. On sale for $95.96. MSRP $134.95. 29% off. 3.9 out of 5 stars

Black Propet Cliff Walker Tall Strap

Black Propet Cliff Walker Tall Strap

Brand Name: Propet
Product Name: Cliff Walker Tall Strap
Gender: Men's
Color: Black
Price: $95.96MSRP: $134.9529% OFF
Rating: 4Rated 4 stars out of 5(17)

Stacy Adams - Maxwell Plain Toe Demi Boot. Color Cognac. On sale for $88.00. MSRP $125.00. 30% off. 4.7 out of 5 stars

Tan Stacy Adams Maxwell Plain Toe Demi Boot

Tan Stacy Adams Maxwell Plain Toe Demi Boot

+2

Brand Name: Stacy Adams
Product Name: Maxwell Plain Toe Demi Boot
Gender: Men's
Color: Cognac
Price: $88.00MSRP: $125.0030% OFF
Rating: 5Rated 5 stars out of 5(43)

Columbia - Newton Ridge™ BC. Color Stone Green/Napa Green. On sale for $81.89. MSRP $100.00. 18% off. 3.9 out of 5 stars

Olive Columbia Newton Ridge™ BC

Olive Columbia Newton Ridge™ BC

+2

Brand Name: Columbia
Product Name: Newton Ridge™ BC
Gender: Men's
Color: Stone Green/Napa Green
Price: $81.89MSRP: $100.0018% OFF
Rating: 4Rated 4 stars out of 5(23)

Bogs - Classic Casual Lace. Color Taupe. On sale for $84.77. MSRP $160.00. 47% off. 2.7 out of 5 stars

Taupe Bogs Classic Casual Lace

Taupe Bogs Classic Casual Lace

Brand Name: Bogs
Product Name: Classic Casual Lace
Gender: Men's
Color: Taupe
Price: $84.77MSRP: $160.0047% OFF
Rating: 3Rated 3 stars out of 5(3)

Steve Madden - Jotting. Color Dark Tan Leather. $99.99.

Brown Steve Madden Jotting

Brown Steve Madden Jotting

+2

Brand Name: Steve Madden
Product Name: Jotting
Gender: Men's
Color: Dark Tan Leather
Price: $99.99
Rating

Columbia - Landroamer Scout Nubuck. Color Black/Canyon Sun. On sale for $75.00. MSRP $100.00. 25% off. 3.0 out of 5 stars

Black Columbia Landroamer Scout Nubuck

Black Columbia Landroamer Scout Nubuck

Brand Name: Columbia
Product Name: Landroamer Scout Nubuck
Gender: Men's
Color: Black/Canyon Sun
Price: $75.00MSRP: $100.0025% OFF
Rating: 3Rated 3 stars out of 5(2)

Steve Madden - Millsen. Color Tan Leather. On sale for $89.70. MSRP $130.00. 31% off.

Tan Steve Madden Millsen

Tan Steve Madden Millsen

Brand Name: Steve Madden
Product Name: Millsen
Gender: Men's
Color: Tan Leather
Price: $89.70MSRP: $130.0031% OFF
Rating

Steve Madden - Jotter. Color Black. $99.99. 4.4 out of 5 stars

Black Steve Madden Jotter

Black Steve Madden Jotter

+2

Brand Name: Steve Madden
Product Name: Jotter
Gender: Men's
Color: Black
Price: $99.99
Rating: 4Rated 4 stars out of 5(23)

Columbia - Landroamer Explorer Waterproof Nubuck. Color Black/Canyon Sun. On sale for $90.00. MSRP $120.00. 25% off. 5.0 out of 5 stars

Black Columbia Landroamer Explorer Waterproof Nubuck

Black Columbia Landroamer Explorer Waterproof Nubuck

+2

Brand Name: Columbia
Product Name: Landroamer Explorer Waterproof Nubuck
Gender: Men's
Color: Black/Canyon Sun
Price: $90.00MSRP: $120.0025% OFF
Rating: 5Rated 5 stars out of 5(2)

L.L.Bean - Stonington Boot Moc Toe Suede. Color Deepest Brown. On sale for $74.50. MSRP $149.00. 50% off. 5.0 out of 5 stars

Brown L.L.Bean Stonington Boot Moc Toe Suede

Brown L.L.Bean Stonington Boot Moc Toe Suede

Brand Name: L.L.Bean
Product Name: Stonington Boot Moc Toe Suede
Gender: Men's
Color: Deepest Brown
Price: $74.50MSRP: $149.0050% OFF
Rating: 5Rated 5 stars out of 5(1)

Rockport - Seamus. Color Dark Brown Suede. On sale for $86.97. MSRP $149.95. 42% off.

Brown Rockport Seamus

Brown Rockport Seamus

+4

Brand Name: Rockport
Product Name: Seamus
Gender: Men's
Color: Dark Brown Suede
Price: $86.97MSRP: $149.9542% OFF
Rating

Tommy Hilfiger - Nyo. Color Black. On sale for $77.37. MSRP $79.95. 3% off.

Black Tommy Hilfiger Nyo

Black Tommy Hilfiger Nyo

Brand Name: Tommy Hilfiger
Product Name: Nyo
Gender: Men's
Color: Black
Price: $77.37MSRP: $79.953% OFF
Rating

L.L.Bean - Rubber Moc. Color Tan/Bean Boot Brown/Gum. $99.00. 4.0 out of 5 stars

Brown L.L.Bean Rubber Moc

Brown L.L.Bean Rubber Moc

Brand Name: L.L.Bean
Product Name: Rubber Moc
Gender: Men's
Color: Tan/Bean Boot Brown/Gum
Price: $99.00
Rating: 4Rated 4 stars out of 5(20)

Columbia - Bugaboot III. Color Cordovan/Rusty 1. On sale for $90.00. MSRP $120.00. 25% off. 4.1 out of 5 stars

Olive Columbia Bugaboot III

Olive Columbia Bugaboot III

+3

Brand Name: Columbia
Product Name: Bugaboot III
Gender: Men's
Color: Cordovan/Rusty 1
Price: $90.00MSRP: $120.0025% OFF
Rating: 4Rated 4 stars out of 5(365)

Dr. Scholl's - Manchester. Color Tan Faux Leather. On sale for $90.47. MSRP $120.00. 25% off. 3.0 out of 5 stars

Tan Dr. Scholl's Manchester

Tan Dr. Scholl's Manchester

+3

Brand Name: Dr. Scholl's
Product Name: Manchester
Gender: Men's
Color: Tan Faux Leather
Price: $90.47MSRP: $120.0025% OFF
Rating: 3Rated 3 stars out of 5(2)

Vance Co. - Alex Chelsea Boot. Color Brown Faux Leather. Low Stock. On sale for $63.25. MSRP $64.99. 3% off. 3.7 out of 5 stars

Low Stock

Brown Vance Co. Alex Chelsea Boot

Brown Vance Co. Alex Chelsea Boot

+4

Brand Name: Vance Co.
Product Name: Alex Chelsea Boot
Gender: Men's
Color: Brown Faux Leather
Price: $63.25MSRP: $64.993% OFF
Rating: 4Rated 4 stars out of 5(34)

Columbia - Landroamer Explorer Waterproof. Color Espresso II/Warp Red. On sale for $90.00. MSRP $120.00. 25% off. 3.7 out of 5 stars

Tan Columbia Landroamer Explorer Waterproof

Tan Columbia Landroamer Explorer Waterproof

+3

Brand Name: Columbia
Product Name: Landroamer Explorer Waterproof
Gender: Men's
Color: Espresso II/Warp Red
Price: $90.00MSRP: $120.0025% OFF
Rating: 4Rated 4 stars out of 5(3)

Thomas & Vine - Keegan. Color Cognac. Low Stock. On sale for $78.03. MSRP $149.99. 48% off. 4.0 out of 5 stars

Low Stock

Tan Thomas & Vine Keegan

Tan Thomas & Vine Keegan

Brand Name: Thomas & Vine
Product Name: Keegan
Gender: Men's
Color: Cognac
Price: $78.03MSRP: $149.9948% OFF
Rating: 4Rated 4 stars out of 5(1)

Join Our List, Get 10% Off

Sign up for Zappos emails—new subscribers get 10% off a future order!* Plus, get early access to sales, coupons, and more. (One code per email address.)