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

Size 8.5 Comfort Ankle Boots and Booties

35 items found

Sort By

Your Selections

Search Results

Harley-Davidson - Grady CT. Color Black. $129.95.

Black Harley-Davidson Grady CT

Black Harley-Davidson Grady CT

Brand Name: Harley-Davidson
Product Name: Grady CT
Gender: Men's
Color: Black
Price: $129.95
Rating

Eastland 1955 Edition - Belgrade. Color Black. On sale for $111.99. MSRP $140.00. 20% off.

Black Eastland 1955 Edition Belgrade

Black Eastland 1955 Edition Belgrade

+2

Brand Name: Eastland 1955 Edition
Product Name: Belgrade
Gender: Men's
Color: Black
Price: $111.99MSRP: $140.0020% OFF
Rating

Dansko - Finnley. Color Black Burnished Nubuck. On sale for $97.97. MSRP $174.95. 44% off. 3.5 out of 5 stars

Black Dansko Finnley

Black Dansko Finnley

Brand Name: Dansko
Product Name: Finnley
Gender: Women's
Color: Black Burnished Nubuck
Price: $97.97MSRP: $174.9544% OFF
Rating: 4Rated 4 stars out of 5(10)

. Carhartt - Millbrook Moc Toe Wedge Boot. Color Grey. On sale for $116.24. MSRP $154.99. 25% off. 4.1 out of 5 stars

Gray Carhartt Millbrook Moc Toe Wedge Boot

Gray Carhartt Millbrook Moc Toe Wedge Boot

Brand Name: Carhartt
Product Name: Millbrook Moc Toe Wedge Boot
Gender: Men's
Color: Grey
Price: $116.24MSRP: $154.9925% OFF
Rating: 4Rated 4 stars out of 5(9)

Danner - Mountain Moc 917 GTX. Color Roasted Pecan. $219.95. 5.0 out of 5 stars

Brown Danner Mountain Moc 917 GTX

Brown Danner Mountain Moc 917 GTX

Brand Name: Danner
Product Name: Mountain Moc 917 GTX
Gender: Men's
Color: Roasted Pecan
Price: $219.95
Rating: 5Rated 5 stars out of 5(1)

. Blundstone - BL587. Color Rustic Black. $199.95. 4.0 out of 5 stars

Black Blundstone BL587

Black Blundstone BL587

Brand Name: Blundstone
Product Name: BL587
Gender: Unisex
Color: Rustic Black
Price: $199.95
Rating: 4Rated 4 stars out of 5(5)

SOREL - Slabtown 62'™ Caribou Hi-Viz Wp. Color Black, Black. Low Stock. On sale for $124.15. MSRP $200.00. 38% off.

Low Stock

Black SOREL Slabtown 62'™ Caribou Hi-Viz Wp

Black SOREL Slabtown 62'™ Caribou Hi-Viz Wp

Brand Name: SOREL
Product Name: Slabtown 62'™ Caribou Hi-Viz Wp
Gender: Men's
Color: Black, Black
Price: $124.15MSRP: $200.0038% OFF
Rating

Dockers - Esmond. Color Cognac. On sale for $62.99. MSRP $85.00. 26% off.

Tan Dockers Esmond

Tan Dockers Esmond

+4

Brand Name: Dockers
Product Name: Esmond
Gender: Men's
Color: Cognac
Price: $62.99MSRP: $85.0026% OFF
Rating

Dansko - Lizanne. Color Black Oiled Pull Up. On sale for $129.46. MSRP $184.95. 30% off. 3.6 out of 5 stars

Black Dansko Lizanne

Black Dansko Lizanne

+3

Brand Name: Dansko
Product Name: Lizanne
Gender: Women's
Color: Black Oiled Pull Up
Price: $129.46MSRP: $184.9530% OFF
Rating: 4Rated 4 stars out of 5(16)

Florsheim - Rucci Wingtip Lace Boot. Color Cognac. On sale for $129.21. MSRP $140.00. 8% off. 5.0 out of 5 stars

Tan Florsheim Rucci Wingtip Lace Boot

Tan Florsheim Rucci Wingtip Lace Boot

+2

Brand Name: Florsheim
Product Name: Rucci Wingtip Lace Boot
Gender: Men's
Color: Cognac
Price: $129.21MSRP: $140.008% OFF
Rating: 5Rated 5 stars out of 5(10)

Nunn Bush - Karnak Plain Toe Boot Chukka. Color Brown. On sale for $79.95. MSRP $110.00. 27% off. 4.6 out of 5 stars

Brown Nunn Bush Karnak Plain Toe Boot Chukka

Brown Nunn Bush Karnak Plain Toe Boot Chukka

+1

Brand Name: Nunn Bush
Product Name: Karnak Plain Toe Boot Chukka
Gender: Men's
Color: Brown
Price: $79.95MSRP: $110.0027% OFF
Rating: 5Rated 5 stars out of 5(17)

Blundstone - BL2412. Color Bordeaux Brush. $194.95. 5.0 out of 5 stars

Burgundy Blundstone BL2412

Burgundy Blundstone BL2412

Brand Name: Blundstone
Product Name: BL2412
Gender: Unisex
Color: Bordeaux Brush
Price: $194.95
Rating: 5Rated 5 stars out of 5(1)

Blundstone - BL2340. Color Brown. $209.95. 5.0 out of 5 stars

Brown Blundstone BL2340

Brown Blundstone BL2340

Brand Name: Blundstone
Product Name: BL2340
Gender: Unisex
Color: Brown
Price: $209.95
Rating: 5Rated 5 stars out of 5(1)

Cole Haan - Originalgrand Remastered Waterproof Chukka Boots. Color Scotch/Alabaster. Low Stock. $200.00. 2.7 out of 5 stars

Low Stock

Tan Cole Haan Originalgrand Remastered Waterproof Chukka Boots

Tan Cole Haan Originalgrand Remastered Waterproof Chukka Boots

+2

Brand Name: Cole Haan
Product Name: Originalgrand Remastered Waterproof Chukka Boots
Gender: Men's
Color: Scotch/Alabaster
Price: $200.00
Rating: 3Rated 3 stars out of 5(3)

Clarks - Shepton. Color Taupe Distressed Leather. On sale for $54.97. MSRP $100.00. 45% off. 2.0 out of 5 stars

Taupe Clarks Shepton

Taupe Clarks Shepton

+4

Brand Name: Clarks
Product Name: Shepton
Gender: Men's
Color: Taupe Distressed Leather
Price: $54.97MSRP: $100.0045% OFF
Rating: 2Rated 2 stars out of 5(4)

Rockport - Flynn. Color Black Leather. On sale for $149.95. MSRP $159.95. 6% off. 2.8 out of 5 stars

Black Rockport Flynn

Black Rockport Flynn

+2

Brand Name: Rockport
Product Name: Flynn
Gender: Men's
Color: Black Leather
Price: $149.95MSRP: $159.956% OFF
Rating: 3Rated 3 stars out of 5(4)

PIKOLINOS - M9K-8028C1. Color Brandy. On sale for $207.00. MSRP $230.00. 10% off.

Brown PIKOLINOS M9K-8028C1

Brown PIKOLINOS M9K-8028C1

+2

Brand Name: PIKOLINOS
Product Name: M9K-8028C1
Gender: Men's
Color: Brandy
Price: $207.00MSRP: $230.0010% OFF
Rating

Born - Ryker. Color Black. $140.00.

Black Born Ryker

Black Born Ryker

+3

Brand Name: Born
Product Name: Ryker
Gender: Men's
Color: Black
Price: $140.00
Rating

Allen Edmonds - Tompkins. Color Black Leather. Low Stock. On sale for $379.00. MSRP $495.00. 23% off.

Low Stock

Black Allen Edmonds Tompkins

Black Allen Edmonds Tompkins

+3

Brand Name: Allen Edmonds
Product Name: Tompkins
Gender: Men's
Color: Black Leather
Price: $379.00MSRP: $495.0023% OFF
Rating

Dunham - Brisco. Color Dark Brown Leather. On sale for $111.58. MSRP $159.95. 30% off. 4.0 out of 5 stars

Brown Dunham Brisco

Brown Dunham Brisco

+3

Brand Name: Dunham
Product Name: Brisco
Gender: Men's
Color: Dark Brown Leather
Price: $111.58MSRP: $159.9530% OFF
Rating: 4Rated 4 stars out of 5(1)

MOON BOOT - Icon Low Quilt. Color Caramel. Low Stock. On sale for $137.79. MSRP $310.00. 56% off.

Low Stock

Brown MOON BOOT Icon Low Quilt

Brown MOON BOOT Icon Low Quilt

Brand Name: MOON BOOT
Product Name: Icon Low Quilt
Gender: Unisex
Color: Caramel
Price: $137.79MSRP: $310.0056% OFF
Rating

Timberland - Britton Road Mid Lace Up Waterproof. Color Wheat Full Grain. On sale for $166.56. MSRP $170.00. 2% off. 4.6 out of 5 stars

Brown Timberland Britton Road Mid Lace Up Waterproof

Brown Timberland Britton Road Mid Lace Up Waterproof

+3

Brand Name: Timberland
Product Name: Britton Road Mid Lace Up Waterproof
Gender: Men's
Color: Wheat Full Grain
Price: $166.56MSRP: $170.002% OFF
Rating: 5Rated 5 stars out of 5(34)

Dansko - Stephanie. Color Black Waterproof Suede. On sale for $117.79. MSRP $189.99. 38% off. 3.7 out of 5 stars

Black Dansko Stephanie

Black Dansko Stephanie

+2

Brand Name: Dansko
Product Name: Stephanie
Gender: Women's
Color: Black Waterproof Suede
Price: $117.79MSRP: $189.9938% OFF
Rating: 4Rated 4 stars out of 5(6)

Rockport - Caspe. Color Taupe Suede. On sale for $110.96. MSRP $149.95. 26% off. 5.0 out of 5 stars

Taupe Rockport Caspe

Taupe Rockport Caspe

+2

Brand Name: Rockport
Product Name: Caspe
Gender: Men's
Color: Taupe Suede
Price: $110.96MSRP: $149.9526% OFF
Rating: 5Rated 5 stars out of 5(1)

MOON BOOT - Icon Low Nylon. Color White. $195.00. 5.0 out of 5 stars

White MOON BOOT Icon Low Nylon

White MOON BOOT Icon Low Nylon

+8

Brand Name: MOON BOOT
Product Name: Icon Low Nylon
Gender: Unisex
Color: White
Price: $195.00
Rating: 5Rated 5 stars out of 5(1)

Stacy Adams - Sandoval Heeled Boot. Color Burgundy. $104.99. 3.9 out of 5 stars

Burgundy Stacy Adams Sandoval Heeled Boot

Burgundy Stacy Adams Sandoval Heeled Boot

Brand Name: Stacy Adams
Product Name: Sandoval Heeled Boot
Gender: Men's
Color: Burgundy
Price: $104.99
Rating: 4Rated 4 stars out of 5(15)

Orthofeet - Verno. Color Black. Low Stock. On sale for $139.99. MSRP $160.00. 13% off.

Low Stock

Black Orthofeet Verno

Black Orthofeet Verno

Brand Name: Orthofeet
Product Name: Verno
Gender: Men's
Color: Black
Price: $139.99MSRP: $160.0013% OFF
Rating

Mephisto - Fosco. Color Tobacco. Low Stock. On sale for $377.52. MSRP $429.00. 12% off.

Low Stock

Brown Mephisto Fosco

Brown Mephisto Fosco

+2

Brand Name: Mephisto
Product Name: Fosco
Gender: Men's
Color: Tobacco
Price: $377.52MSRP: $429.0012% OFF
Rating

Eastland 1955 Edition - Allagash Standard. Color Oak. On sale for $121.80. MSRP $145.00. 16% off.

Brown Eastland 1955 Edition Allagash Standard

Brown Eastland 1955 Edition Allagash Standard

+3

Brand Name: Eastland 1955 Edition
Product Name: Allagash Standard
Gender: Men's
Color: Oak
Price: $121.80MSRP: $145.0016% OFF
Rating

Eastland 1955 Edition - Chimney Pond. Color Oak. On sale for $130.50. MSRP $145.00. 10% off.

Brown Eastland 1955 Edition Chimney Pond

Brown Eastland 1955 Edition Chimney Pond

+2

Brand Name: Eastland 1955 Edition
Product Name: Chimney Pond
Gender: Men's
Color: Oak
Price: $130.50MSRP: $145.0010% OFF
Rating

Rockport - Seamus. Color Black Leather. $149.95.

Black Rockport Seamus

Black Rockport Seamus

+4

Brand Name: Rockport
Product Name: Seamus
Gender: Men's
Color: Black Leather
Price: $149.95
Rating

Josef Seibel - Erroll 50. Color Fango. $165.00.

Tan Josef Seibel Erroll 50

Tan Josef Seibel Erroll 50

+2 colors/patterns

Brand Name: Josef Seibel
Product Name: Erroll 50
Gender: Men's
Color: Fango
Price: $165.00
Rating

COACH - Caiden Boot. Color Black. Low Stock. $295.00.

Low Stock

Black COACH Caiden Boot

Black COACH Caiden Boot

+2

Brand Name: COACH
Product Name: Caiden Boot
Gender: Men's
Color: Black
Price: $295.00
Rating

MOON BOOT - Icon Low Optical. Color Lilac/Cyber Lime. Low Stock. On sale for $227.95. MSRP $240.00. 5% off.

Low Stock

Multi MOON BOOT Icon Low Optical

Multi MOON BOOT Icon Low Optical

+2

Brand Name: MOON BOOT
Product Name: Icon Low Optical
Gender: Unisex
Color: Lilac/Cyber Lime
Price: $227.95MSRP: $240.005% OFF
Rating

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

Black Polo Ralph Lauren Ranger Mid Camo Suede Boot

Black 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: $198.00
Rating

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.)