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

Size 10 Ankle Casual Products

355 items found

Sort By

Your Selections

Search Results

Bogs - Kicker Rain Chelsea II. Color Black Multi. $95.00. 4.3 out of 5 stars

Black Bogs Kicker Rain Chelsea II

Black Bogs Kicker Rain Chelsea II

+4

Brand Name: Bogs
Product Name: Kicker Rain Chelsea II
Gender: Men's
Color: Black Multi
Price: $95.00
Rating: 4Rated 4 stars out of 5(52)

Nunn Bush - Circuit DC Plain Toe Chukka. Color Cognac. On sale for $59.95. MSRP $90.00. 33% off. 3.8 out of 5 stars

Tan Nunn Bush Circuit DC Plain Toe Chukka

Tan Nunn Bush Circuit DC Plain Toe Chukka

+3

Brand Name: Nunn Bush
Product Name: Circuit DC Plain Toe Chukka
Gender: Men's
Color: Cognac
Price: $59.95MSRP: $90.0033% OFF
Rating: 4Rated 4 stars out of 5(49)

Hunter - Original Play Boot Chelsea. Color Black. $130.00. 4.6 out of 5 stars

Black Hunter Original Play Boot Chelsea

Black Hunter Original Play Boot Chelsea

+4

Brand Name: Hunter
Product Name: Original Play Boot Chelsea
Gender: Men's
Color: Black
Price: $130.00
Rating: 5Rated 5 stars out of 5(29)

Dr. Martens - Combs Leather. Color Dark Brown Crazy Horse. $130.00. 4.5 out of 5 stars

Brown Dr. Martens Combs Leather

Brown Dr. Martens Combs Leather

+3

Brand Name: Dr. Martens
Product Name: Combs Leather
Gender: Unisex
Color: Dark Brown Crazy Horse
Price: $130.00
Rating: 5Rated 5 stars out of 5(77)

Dunham - 8000 Mid Boot. Color Black Leather. On sale for $169.95. MSRP $189.95. 11% off. 4.3 out of 5 stars

Black Dunham 8000 Mid Boot

Black Dunham 8000 Mid Boot

+2

Brand Name: Dunham
Product Name: 8000 Mid Boot
Gender: Men's
Color: Black Leather
Price: $169.95MSRP: $189.9511% OFF
Rating: 4Rated 4 stars out of 5(120)

Blundstone - BL558. Color Black. $209.95. 4.1 out of 5 stars

Black Blundstone BL558

Black Blundstone BL558

Brand Name: Blundstone
Product Name: BL558
Gender: Unisex
Color: Black
Price: $209.95
Rating: 4Rated 4 stars out of 5(11)

Bogs - Kicker Rain Chelsea Neo. Color Dark Green Multi 1. $100.00. 4.3 out of 5 stars

Green Bogs Kicker Rain Chelsea Neo

Green Bogs Kicker Rain Chelsea Neo

+3

Brand Name: Bogs
Product Name: Kicker Rain Chelsea Neo
Gender: Men's
Color: Dark Green Multi 1
Price: $100.00
Rating: 4Rated 4 stars out of 5(52)

Nunn Bush - Odell 2.0 Wingtip Dress Casual Chukka Leather Boot. Color Tan. On sale for $84.99. MSRP $120.00. 29% off. 4.6 out of 5 stars

Tan Nunn Bush Odell 2.0 Wingtip Dress Casual Chukka Leather Boot

Tan Nunn Bush Odell 2.0 Wingtip Dress Casual Chukka Leather Boot

+1

Brand Name: Nunn Bush
Product Name: Odell 2.0 Wingtip Dress Casual Chukka Leather Boot
Gender: Men's
Color: Tan
Price: $84.99MSRP: $120.0029% OFF
Rating: 5Rated 5 stars out of 5(9)

Dr. Martens - 1460 Pascal. Color Light Tan Mini Leopard Spot. On sale for $161.95. MSRP $180.00. 10% off. 4.4 out of 5 stars

Brown Dr. Martens 1460 Pascal

Brown Dr. Martens 1460 Pascal

+3

Brand Name: Dr. Martens
Product Name: 1460 Pascal
Gender: Unisex
Color: Light Tan Mini Leopard Spot
Price: $161.95MSRP: $180.0010% OFF
Rating: 4Rated 4 stars out of 5(17)

Nunn Bush - Otis 2.0 Chelsea Fashion Leather Boot. Color Brown. On sale for $84.99. MSRP $120.00. 29% off. 4.3 out of 5 stars

Brown Nunn Bush Otis 2.0 Chelsea Fashion Leather Boot

Brown Nunn Bush Otis 2.0 Chelsea Fashion Leather Boot

+3

Brand Name: Nunn Bush
Product Name: Otis 2.0 Chelsea Fashion Leather Boot
Gender: Men's
Color: Brown
Price: $84.99MSRP: $120.0029% OFF
Rating: 4Rated 4 stars out of 5(7)

L.L.Bean - 6" Bean Boots. Color Tan/Bean Boot Brown/Gum. $139.00. 4.5 out of 5 stars

Brown L.L.Bean 6" Bean Boots

Brown L.L.Bean 6" Bean Boots

Brand Name: L.L.Bean
Product Name: 6" Bean Boots
Gender: Men's
Color: Tan/Bean Boot Brown/Gum
Price: $139.00
Rating: 5Rated 5 stars out of 5(1105)

Florsheim - Norwalk Plain Toe Chukka Boot. Color Black Crazy Horse. $150.00. 4.6 out of 5 stars

Black Florsheim Norwalk Plain Toe Chukka Boot

Black Florsheim Norwalk Plain Toe Chukka Boot

Brand Name: Florsheim
Product Name: Norwalk Plain Toe Chukka Boot
Gender: Men's
Color: Black Crazy Horse
Price: $150.00
Rating: 5Rated 5 stars out of 5(67)

Dunham - Alpine Mid Boots. Color Dark Brown Leather. On sale for $151.26. MSRP $164.95. 8% off. 3.2 out of 5 stars

Brown Dunham Alpine Mid Boots

Brown Dunham Alpine Mid Boots

+3

Brand Name: Dunham
Product Name: Alpine Mid Boots
Gender: Men's
Color: Dark Brown Leather
Price: $151.26MSRP: $164.958% OFF
Rating: 3Rated 3 stars out of 5(4)

Blundstone - BL1306. Color Rustic Brown. $209.95. 3.2 out of 5 stars

Brown Blundstone BL1306

Brown Blundstone BL1306

Brand Name: Blundstone
Product Name: BL1306
Gender: Unisex
Color: Rustic Brown
Price: $209.95
Rating: 3Rated 3 stars out of 5(6)

Bogs - Sauvie Chelsea II. Color Black. On sale for $100.00. MSRP $110.00. 9% off. 3.9 out of 5 stars

Black Bogs Sauvie Chelsea II

Black Bogs Sauvie Chelsea II

+1

Brand Name: Bogs
Product Name: Sauvie Chelsea II
Gender: Men's
Color: Black
Price: $100.00MSRP: $110.009% OFF
Rating: 4Rated 4 stars out of 5(84)

SOREL - Cyprus Chelsea Waterproof. Color Velvet Tan/Gum 10. $124.95.

Brown SOREL Cyprus Chelsea Waterproof

Brown SOREL Cyprus Chelsea Waterproof

+3

Brand Name: SOREL
Product Name: Cyprus Chelsea Waterproof
Gender: Men's
Color: Velvet Tan/Gum 10
Price: $124.95
Rating

Tommy Hilfiger - Bage. Color Black Tumble. On sale for $69.49. MSRP $119.00. 42% off. 5.0 out of 5 stars

Black Tommy Hilfiger Bage

Black Tommy Hilfiger Bage

+4

Brand Name: Tommy Hilfiger
Product Name: Bage
Gender: Men's
Color: Black Tumble
Price: $69.49MSRP: $119.0042% OFF
Rating: 5Rated 5 stars out of 5(1)

. Florsheim - Midtown Plain Toe Zipper Boot. Color Brown Smooth. On sale for $134.71. MSRP $150.00. 10% off. 4.6 out of 5 stars

Brown Florsheim Midtown Plain Toe Zipper Boot

Brown Florsheim Midtown Plain Toe Zipper Boot

+1

Brand Name: Florsheim
Product Name: Midtown Plain Toe Zipper Boot
Gender: Men's
Color: Brown Smooth
Price: $134.71MSRP: $150.0010% OFF
Rating: 5Rated 5 stars out of 5(519)

Born - Harrison. Color Black Full Grain. $144.95. 4.3 out of 5 stars

Black Born Harrison

Black Born Harrison

+2

Brand Name: Born
Product Name: Harrison
Gender: Men's
Color: Black Full Grain
Price: $144.95
Rating: 4Rated 4 stars out of 5(114)

. Steve Madden - Hestonn. Color Tan Leather. Low Stock. On sale for $89.99. MSRP $99.99. 10% off. 3.8 out of 5 stars

Low Stock

Tan Steve Madden Hestonn

Tan Steve Madden Hestonn

+3

Brand Name: Steve Madden
Product Name: Hestonn
Gender: Men's
Color: Tan Leather
Price: $89.99MSRP: $99.9910% OFF
Rating: 4Rated 4 stars out of 5(73)

L.L.Bean - Stonington Boots Moc Toe. Color Black. $148.95. 4.5 out of 5 stars

Black L.L.Bean Stonington Boots Moc Toe

Black L.L.Bean Stonington Boots Moc Toe

+2

Brand Name: L.L.Bean
Product Name: Stonington Boots Moc Toe
Gender: Men's
Color: Black
Price: $148.95
Rating: 5Rated 5 stars out of 5(459)

Born - Reed. Color Black. $150.00.

Black Born Reed

Black Born Reed

+2

Brand Name: Born
Product Name: Reed
Gender: Men's
Color: Black
Price: $150.00
Rating

. Dr. Martens - 1460 Mono Boot. Color Black Smooth. On sale for $127.50. MSRP $170.00. 25% off. 4.1 out of 5 stars

Black Dr. Martens 1460 Mono Boot

Black Dr. Martens 1460 Mono Boot

Brand Name: Dr. Martens
Product Name: 1460 Mono Boot
Gender: Unisex
Color: Black Smooth
Price: $127.50MSRP: $170.0025% OFF
Rating: 4Rated 4 stars out of 5(71)

Deer Stags - Rockland. Color Redwood/Dark Brown. On sale for $64.99. MSRP $90.00. 28% off. 3.7 out of 5 stars

Brown Deer Stags Rockland

Brown Deer Stags Rockland

+1

Brand Name: Deer Stags
Product Name: Rockland
Gender: Men's
Color: Redwood/Dark Brown
Price: $64.99MSRP: $90.0028% OFF
Rating: 4Rated 4 stars out of 5(31)

Blundstone - BL519. Color Stout Brown/Green. $204.95. 3.4 out of 5 stars

Black Blundstone BL519

Black Blundstone BL519

Brand Name: Blundstone
Product Name: BL519
Gender: Unisex
Color: Stout Brown/Green
Price: $204.95
Rating: 3Rated 3 stars out of 5(5)

Rockport - Classic Break Chukka. Color Dark Brown Leather. On sale for $119.99. MSRP $159.95. 25% off. 4.3 out of 5 stars

Brown Rockport Classic Break Chukka

Brown Rockport Classic Break Chukka

Brand Name: Rockport
Product Name: Classic Break Chukka
Gender: Men's
Color: Dark Brown Leather
Price: $119.99MSRP: $159.9525% OFF
Rating: 4Rated 4 stars out of 5(212)

. Dr. Martens - Combs Tech. Color Black. On sale for $99.95. MSRP $120.00. 17% off. 4.4 out of 5 stars

Black Dr. Martens Combs Tech

Black Dr. Martens Combs Tech

+2

Brand Name: Dr. Martens
Product Name: Combs Tech
Gender: Unisex
Color: Black
Price: $99.95MSRP: $120.0017% OFF
Rating: 4Rated 4 stars out of 5(52)

The North Face - ThermoBall™ Traction Bootsies. Color None. $69.00. 4.8 out of 5 stars

White The North Face ThermoBall™ Traction Bootsies

White The North Face ThermoBall™ Traction Bootsies

+2

Brand Name: The North Face
Product Name: ThermoBall™ Traction Bootsies
Gender: Men's
Color: None
Price: $69.00
Rating: 5Rated 5 stars out of 5(326)

Dr. Martens - Combs Jungle Zip Casual Boots. Color Dark Khaki. On sale for $83.97. MSRP $140.00. 40% off. 2.5 out of 5 stars

Khaki Dr. Martens Combs Jungle Zip Casual Boots

Khaki Dr. Martens Combs Jungle Zip Casual Boots

+3

Brand Name: Dr. Martens
Product Name: Combs Jungle Zip Casual Boots
Gender: Unisex
Color: Dark Khaki
Price: $83.97MSRP: $140.0040% OFF
Rating: 3Rated 3 stars out of 5(2)

Nunn Bush - Karnak Plain Toe Boot Chukka. Color Brown. On sale for $84.99. MSRP $120.00. 29% 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: $84.99MSRP: $120.0029% OFF
Rating: 5Rated 5 stars out of 5(17)

Blundstone - BL1944. Color Rustic Brown/Mustard. $219.95. 4.3 out of 5 stars

Brown Blundstone BL1944

Brown Blundstone BL1944

Brand Name: Blundstone
Product Name: BL1944
Gender: Unisex
Color: Rustic Brown/Mustard
Price: $219.95
Rating: 4Rated 4 stars out of 5(3)

Nunn Bush - Ozark 2.0 Plain Toe Chukka Leather Boot. Color Brown. On sale for $84.99. MSRP $120.00. 29% off. 4.6 out of 5 stars

Brown Nunn Bush Ozark 2.0 Plain Toe Chukka Leather Boot

Brown Nunn Bush Ozark 2.0 Plain Toe Chukka Leather Boot

+3

Brand Name: Nunn Bush
Product Name: Ozark 2.0 Plain Toe Chukka Leather Boot
Gender: Men's
Color: Brown
Price: $84.99MSRP: $120.0029% OFF
Rating: 5Rated 5 stars out of 5(8)

Dr. Martens Work - 2976 Slip Resistant Chelsea Boots. Color Dark Tan. On sale for $113.05. MSRP $180.00. 37% off. 3.8 out of 5 stars

Brown Dr. Martens Work 2976 Slip Resistant Chelsea Boots

Brown Dr. Martens Work 2976 Slip Resistant Chelsea Boots

Brand Name: Dr. Martens Work
Product Name: 2976 Slip Resistant Chelsea Boots
Gender: Unisex
Color: Dark Tan
Price: $113.05MSRP: $180.0037% OFF
Rating: 4Rated 4 stars out of 5(4)

Blundstone - BL2340. Color Brown. $219.95. 5.0 out of 5 stars

Brown Blundstone BL2340

Brown Blundstone BL2340

Brand Name: Blundstone
Product Name: BL2340
Gender: Unisex
Color: Brown
Price: $219.95
Rating: 5Rated 5 stars out of 5(1)

KEEN Utility - Skokie Waterproof Work Boot (Soft Toe). Color Forest Night/Black. $144.95.

Green KEEN Utility Skokie Waterproof Work Boot (Soft Toe)

Green KEEN Utility Skokie Waterproof Work Boot (Soft Toe)

+2

Brand Name: KEEN Utility
Product Name: Skokie Waterproof Work Boot (Soft Toe)
Gender: Men's
Color: Forest Night/Black
Price: $144.95
Rating

L.L.Bean - Rubber Moc. Color Tan/Bean Boot Brown/Gum. Low Stock. $99.00. 3.9 out of 5 stars

Low Stock

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(135)

Steve Madden - Montreaux. Color Tan. On sale for $97.50. MSRP $130.00. 25% off.

Tan Steve Madden Montreaux

Tan Steve Madden Montreaux

Brand Name: Steve Madden
Product Name: Montreaux
Gender: Men's
Color: Tan
Price: $97.50MSRP: $130.0025% OFF
Rating

Dr. Martens - 1460 Ambassador Leather Lace Up Boots. Color Cashew. $170.00. 5.0 out of 5 stars

Beige Dr. Martens 1460 Ambassador Leather Lace Up Boots

Beige Dr. Martens 1460 Ambassador Leather Lace Up Boots

+2

Brand Name: Dr. Martens
Product Name: 1460 Ambassador Leather Lace Up Boots
Gender: Unisex
Color: Cashew
Price: $170.00
Rating: 5Rated 5 stars out of 5(4)

Born - Nigel Boot. Color Brown/Dark Brown Combo. $150.00. 4.2 out of 5 stars

Brown Born Nigel Boot

Brown Born Nigel Boot

+3

Brand Name: Born
Product Name: Nigel Boot
Gender: Men's
Color: Brown/Dark Brown Combo
Price: $150.00
Rating: 4Rated 4 stars out of 5(148)

L.L.Bean - Hybrid Wellie. Color Deepest Brown. On sale for $74.00. MSRP $99.00. 25% off. 4.5 out of 5 stars

Brown L.L.Bean Hybrid Wellie

Brown L.L.Bean Hybrid Wellie

+2 colors/patterns

Brand Name: L.L.Bean
Product Name: Hybrid Wellie
Gender: Men's
Color: Deepest Brown
Price: $74.00MSRP: $99.0025% OFF
Rating: 4Rated 4 stars out of 5(43)

Born - Lincoln. Color Dark Brown (Bark). $100.00.

Brown Born Lincoln

Brown Born Lincoln

+2

Brand Name: Born
Product Name: Lincoln
Gender: Men's
Color: Dark Brown (Bark)
Price: $100.00
Rating

Nunn Bush - Excavate Plain Toe Chukka Boot. Color Tan. On sale for $64.95. MSRP $95.00. 32% off. 4.4 out of 5 stars

Tan Nunn Bush Excavate Plain Toe Chukka Boot

Tan Nunn Bush Excavate Plain Toe Chukka Boot

+1

Brand Name: Nunn Bush
Product Name: Excavate Plain Toe Chukka Boot
Gender: Men's
Color: Tan
Price: $64.95MSRP: $95.0032% OFF
Rating: 4Rated 4 stars out of 5(23)

Steve Madden - Noby. Color Tan. On sale for $150.00. MSRP $190.00. 21% off. 4.0 out of 5 stars

Tan Steve Madden Noby

Tan Steve Madden Noby

+1

Brand Name: Steve Madden
Product Name: Noby
Gender: Men's
Color: Tan
Price: $150.00MSRP: $190.0021% OFF
Rating: 4Rated 4 stars out of 5(2)

Clarks - Shepton Easy. Color Black Leather. On sale for $65.97. MSRP $120.00. 45% off.

Black Clarks Shepton Easy

Black Clarks Shepton Easy

+2

Brand Name: Clarks
Product Name: Shepton Easy
Gender: Men's
Color: Black Leather
Price: $65.97MSRP: $120.0045% OFF
Rating

Eastland 1955 Edition - Jason. Color Tan. On sale for $67.50. MSRP $90.00. 25% off.

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: $67.50MSRP: $90.0025% OFF
Rating

Born - Hemlock. Color Black Full Grain. $144.95. 4.3 out of 5 stars

Black Born Hemlock

Black Born Hemlock

+2

Brand Name: Born
Product Name: Hemlock
Gender: Men's
Color: Black Full Grain
Price: $144.95
Rating: 4Rated 4 stars out of 5(189)

Ariat - Recon Lace. Color Distressed Brown. $159.95. 4.1 out of 5 stars

Brown Ariat Recon Lace

Brown Ariat Recon Lace

Brand Name: Ariat
Product Name: Recon Lace
Gender: Men's
Color: Distressed Brown
Price: $159.95
Rating: 4Rated 4 stars out of 5(130)

Dr. Martens - Embury. Color Dark Brown Crazy Horse. $130.00. 4.1 out of 5 stars

Brown Dr. Martens Embury

Brown Dr. Martens Embury

+3

Brand Name: Dr. Martens
Product Name: Embury
Gender: Unisex
Color: Dark Brown Crazy Horse
Price: $130.00
Rating: 4Rated 4 stars out of 5(102)

Dunham - Brisco. Color Black Leather. On sale for $111.75. MSRP $159.95. 30% off. 4.0 out of 5 stars

Black Dunham Brisco

Black Dunham Brisco

+3

Brand Name: Dunham
Product Name: Brisco
Gender: Men's
Color: Black Leather
Price: $111.75MSRP: $159.9530% OFF
Rating: 4Rated 4 stars out of 5(1)

. Clarks - Shacre Boot. Color Beeswax Leather. On sale for $64.99. MSRP $110.00. 41% off. 4.2 out of 5 stars

Brown Clarks Shacre Boot

Brown Clarks Shacre Boot

+4

Brand Name: Clarks
Product Name: Shacre Boot
Gender: Men's
Color: Beeswax Leather
Price: $64.99MSRP: $110.0041% OFF
Rating: 4Rated 4 stars out of 5(67)

Red Wing Heritage - 6" Iron Ranger Lug. Color Amber Harness. $349.99. 4.5 out of 5 stars

Brown Red Wing Heritage 6" Iron Ranger Lug

Brown Red Wing Heritage 6" Iron Ranger Lug

+4

Brand Name: Red Wing Heritage
Product Name: 6" Iron Ranger Lug
Gender: Men's
Color: Amber Harness
Price: $349.99
Rating: 5Rated 5 stars out of 5(159)

Dr. Martens - 1460 Inferno. Color Cherry Red. $170.00.

Red Dr. Martens 1460 Inferno

Red Dr. Martens 1460 Inferno

Brand Name: Dr. Martens
Product Name: 1460 Inferno
Gender: Unisex
Color: Cherry Red
Price: $170.00
Rating

Dr. Martens - 101 Yellow Stitch. Color Black Smooth. On sale for $134.95. MSRP $160.00. 16% off. 3.8 out of 5 stars

Black Dr. Martens 101 Yellow Stitch

Black Dr. Martens 101 Yellow Stitch

Brand Name: Dr. Martens
Product Name: 101 Yellow Stitch
Gender: Unisex
Color: Black Smooth
Price: $134.95MSRP: $160.0016% OFF
Rating: 4Rated 4 stars out of 5(5)

Johnston & Murphy - XC Flex Raleigh Cap Toe Zip. Color Dark Tan Full Grain. $184.95. 4.3 out of 5 stars

Tan Johnston & Murphy XC Flex Raleigh Cap Toe Zip

Tan Johnston & Murphy XC Flex Raleigh Cap Toe Zip

+2

Brand Name: Johnston & Murphy
Product Name: XC Flex Raleigh Cap Toe Zip
Gender: Men's
Color: Dark Tan Full Grain
Price: $184.95
Rating: 4Rated 4 stars out of 5(167)

Dr. Martens - 101. Color Dark Brown Crazy Horse. On sale for $120.00. MSRP $160.00. 25% off. 4.7 out of 5 stars

Brown Dr. Martens 101

Brown Dr. Martens 101

Brand Name: Dr. Martens
Product Name: 101
Gender: Unisex
Color: Dark Brown Crazy Horse
Price: $120.00MSRP: $160.0025% OFF
Rating: 5Rated 5 stars out of 5(6)

Dockers - Dudley. Color Dark Brown. On sale for $44.98. MSRP $85.00. 47% off. 3.3 out of 5 stars

Brown Dockers Dudley

Brown Dockers Dudley

+2

Brand Name: Dockers
Product Name: Dudley
Gender: Men's
Color: Dark Brown
Price: $44.98MSRP: $85.0047% OFF
Rating: 3Rated 3 stars out of 5(3)

Rockport - Evan Waterproof Boots. Color Dark Taupe Multi. On sale for $89.97. MSRP $149.95. 40% off. 3.5 out of 5 stars

Brown Rockport Evan Waterproof Boots

Brown Rockport Evan Waterproof Boots

+3

Brand Name: Rockport
Product Name: Evan Waterproof Boots
Gender: Men's
Color: Dark Taupe Multi
Price: $89.97MSRP: $149.9540% OFF
Rating: 4Rated 4 stars out of 5(2)

Red Wing Heritage - Work Chukka. Color Briar Oil Slick. $289.99. 4.5 out of 5 stars

Mahogany Red Wing Heritage Work Chukka

Mahogany Red Wing Heritage Work Chukka

Brand Name: Red Wing Heritage
Product Name: Work Chukka
Gender: Men's
Color: Briar Oil Slick
Price: $289.99
Rating: 4Rated 4 stars out of 5(87)

Nunn Bush - Denali Plain Toe Chukka. Color Black. On sale for $84.99. MSRP $120.00. 29% off. 4.4 out of 5 stars

Black Nunn Bush Denali Plain Toe Chukka

Black Nunn Bush Denali Plain Toe Chukka

+2

Brand Name: Nunn Bush
Product Name: Denali Plain Toe Chukka
Gender: Men's
Color: Black
Price: $84.99MSRP: $120.0029% OFF
Rating: 4Rated 4 stars out of 5(100)

L.L.Bean - Trail Model X Mid Waterproof Hiker. Color Deepest Brown. $119.00.

Brown L.L.Bean Trail Model X Mid Waterproof Hiker

Brown L.L.Bean Trail Model X Mid Waterproof Hiker

+2

Brand Name: L.L.Bean
Product Name: Trail Model X Mid Waterproof Hiker
Gender: Men's
Color: Deepest Brown
Price: $119.00
Rating

Dr. Martens - 2976 Leather Chelsea Boots. Color Cashew. On sale for $144.50. MSRP $170.00. 15% off. 3.6 out of 5 stars

Beige Dr. Martens 2976 Leather Chelsea Boots

Beige Dr. Martens 2976 Leather Chelsea Boots

+2

Brand Name: Dr. Martens
Product Name: 2976 Leather Chelsea Boots
Gender: Unisex
Color: Cashew
Price: $144.50MSRP: $170.0015% OFF
Rating: 4Rated 4 stars out of 5(8)

Eastland 1955 Edition - Jack. Color Peanut. On sale for $89.97. MSRP $125.00. 28% off. 4.2 out of 5 stars

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: $89.97MSRP: $125.0028% OFF
Rating: 4Rated 4 stars out of 5(8)

Dr. Martens - 2976 Yellow Stitch Smooth Leather Chelsea Boots. Color Dark Brown Crazy Horse. On sale for $134.95. MSRP $170.00. 21% off. 3.8 out of 5 stars

Brown Dr. Martens 2976 Yellow Stitch Smooth Leather Chelsea Boots

Brown Dr. Martens 2976 Yellow Stitch Smooth Leather Chelsea Boots

+2

Brand Name: Dr. Martens
Product Name: 2976 Yellow Stitch Smooth Leather Chelsea Boots
Gender: Unisex
Color: Dark Brown Crazy Horse
Price: $134.95MSRP: $170.0021% OFF
Rating: 4Rated 4 stars out of 5(38)

Laredo - Fletcher. Color Tan. $154.95. 4.2 out of 5 stars

Tan Laredo Fletcher

Tan Laredo Fletcher

Brand Name: Laredo
Product Name: Fletcher
Gender: Men's
Color: Tan
Price: $154.95
Rating: 4Rated 4 stars out of 5(32)

Birkenstock - Uppsala Mid Lace-Up - Suede (Men). Color Black 1. $160.00. 5.0 out of 5 stars

Black Birkenstock Uppsala Mid Lace-Up - Suede (Men)

Black Birkenstock Uppsala Mid Lace-Up - Suede (Men)

+2

Brand Name: Birkenstock
Product Name: Uppsala Mid Lace-Up - Suede (Men)
Gender: Men's
Color: Black 1
Price: $160.00
Rating: 5Rated 5 stars out of 5(5)

Red Wing Heritage - Classic Chelsea. Color Black Harness. On sale for $298.95. MSRP $329.99. 9% off. 4.8 out of 5 stars

Black Red Wing Heritage Classic Chelsea

Black Red Wing Heritage Classic Chelsea

+3

Brand Name: Red Wing Heritage
Product Name: Classic Chelsea
Gender: Men's
Color: Black Harness
Price: $298.95MSRP: $329.999% OFF
Rating: 5Rated 5 stars out of 5(13)

Blundstone - BL566. Color Black. $229.95. 5.0 out of 5 stars

Black Blundstone BL566

Black Blundstone BL566

Brand Name: Blundstone
Product Name: BL566
Gender: Unisex
Color: Black
Price: $229.95
Rating: 5Rated 5 stars out of 5(1)

Stacy Adams - Maury Cap Toe Chelsea Boot. Color Black. On sale for $99.99. MSRP $145.00. 31% off. 4.7 out of 5 stars

Black Stacy Adams Maury Cap Toe Chelsea Boot

Black Stacy Adams Maury Cap Toe Chelsea Boot

+3

Brand Name: Stacy Adams
Product Name: Maury Cap Toe Chelsea Boot
Gender: Men's
Color: Black
Price: $99.99MSRP: $145.0031% OFF
Rating: 5Rated 5 stars out of 5(41)

Dr. Martens - 1460 Smooth Leather Lace Up Boots. Color Black Smooth. $169.95. 4.3 out of 5 stars

Black Dr. Martens 1460 Smooth Leather Lace Up Boots

Brand Name: Dr. Martens
Product Name: 1460 Smooth Leather Lace Up Boots
Gender: Unisex
Color: Black Smooth
Price: $169.95
Rating: 4Rated 4 stars out of 5(746)

SOREL - Carson™ Chukka WP. Color Major/Wet Sand. On sale for $95.97. MSRP $160.00. 40% off. 3.8 out of 5 stars

Brown SOREL Carson™ Chukka WP

Brown SOREL Carson™ Chukka WP

Brand Name: SOREL
Product Name: Carson™ Chukka WP
Gender: Men's
Color: Major/Wet Sand
Price: $95.97MSRP: $160.0040% OFF
Rating: 4Rated 4 stars out of 5(18)

Dr. Martens - 1460 Pascal Bex. Color Black Pisa. On sale for $149.95. MSRP $180.00. 17% off. 4.4 out of 5 stars

Black Dr. Martens 1460 Pascal Bex

Black Dr. Martens 1460 Pascal Bex

Brand Name: Dr. Martens
Product Name: 1460 Pascal Bex
Gender: Unisex
Color: Black Pisa
Price: $149.95MSRP: $180.0017% OFF
Rating: 4Rated 4 stars out of 5(42)

Columbia - Landroamer Explorer Waterproof Nubuck. Color Curry/Poppy Red. On sale for $83.96. MSRP $120.00. 30% off. 5.0 out of 5 stars

Tan Columbia Landroamer Explorer Waterproof Nubuck

Tan Columbia Landroamer Explorer Waterproof Nubuck

+2

Brand Name: Columbia
Product Name: Landroamer Explorer Waterproof Nubuck
Gender: Men's
Color: Curry/Poppy Red
Price: $83.96MSRP: $120.0030% OFF
Rating: 5Rated 5 stars out of 5(2)

Ariat - Wexford Waterproof. Color Dark Brown. $209.95. 4.5 out of 5 stars

Brown Ariat Wexford Waterproof

Brown Ariat Wexford Waterproof

+2

Brand Name: Ariat
Product Name: Wexford Waterproof
Gender: Men's
Color: Dark Brown
Price: $209.95
Rating: 5Rated 5 stars out of 5(234)

Nunn Bush - Otto Plain Toe Chukka Boot. Color Navy. On sale for $69.99. MSRP $120.00. 42% off. 4.1 out of 5 stars

Navy Nunn Bush Otto Plain Toe Chukka Boot

Navy Nunn Bush Otto Plain Toe Chukka Boot

+4

Brand Name: Nunn Bush
Product Name: Otto Plain Toe Chukka Boot
Gender: Men's
Color: Navy
Price: $69.99MSRP: $120.0042% OFF
Rating: 4Rated 4 stars out of 5(27)

Tommy Hilfiger - Vitus. Color Black. On sale for $75.39. MSRP $119.00. 37% off.

Black Tommy Hilfiger Vitus

Black Tommy Hilfiger Vitus

Brand Name: Tommy Hilfiger
Product Name: Vitus
Gender: Men's
Color: Black
Price: $75.39MSRP: $119.0037% OFF
Rating

Rockport - Flynn. Color Medium Natural Leather. $159.95. 2.8 out of 5 stars

Brown Rockport Flynn

Brown Rockport Flynn

+2

Brand Name: Rockport
Product Name: Flynn
Gender: Men's
Color: Medium Natural Leather
Price: $159.95
Rating: 3Rated 3 stars out of 5(5)

Clarks - Desert Boot. Color Sand Suede 1. $150.00. 4.4 out of 5 stars

Beige Clarks Desert Boot

Beige Clarks Desert Boot

+4

Brand Name: Clarks
Product Name: Desert Boot
Gender: Men's
Color: Sand Suede 1
Price: $150.00
Rating: 4Rated 4 stars out of 5(779)

Ariat - Spitfire. Color American Flag Print. $129.95. 4.5 out of 5 stars

Multi Ariat Spitfire

Multi Ariat Spitfire

+5

Brand Name: Ariat
Product Name: Spitfire
Gender: Men's
Color: American Flag Print
Price: $129.95
Rating: 5Rated 5 stars out of 5(395)

Ariat - Midtown Rambler. Color Barn Brown. $169.95. 4.4 out of 5 stars

Brown Ariat Midtown Rambler

Brown Ariat Midtown Rambler

+2 colors/patterns

Brand Name: Ariat
Product Name: Midtown Rambler
Gender: Men's
Color: Barn Brown
Price: $169.95
Rating: 4Rated 4 stars out of 5(336)

Nunn Bush - Karnak Moc Toe Boot Lightweight Comfortable Chukka. Color Tan. On sale for $84.99. MSRP $120.00. 29% off. 4.3 out of 5 stars

Tan Nunn Bush Karnak Moc Toe Boot Lightweight Comfortable Chukka

Tan Nunn Bush Karnak Moc Toe Boot Lightweight Comfortable Chukka

+1

Brand Name: Nunn Bush
Product Name: Karnak Moc Toe Boot Lightweight Comfortable Chukka
Gender: Men's
Color: Tan
Price: $84.99MSRP: $120.0029% OFF
Rating: 4Rated 4 stars out of 5(10)

OluKai - Papaku 'Ili. Color Black/Black. $160.00. 4.0 out of 5 stars

Black OluKai Papaku 'Ili

Black OluKai Papaku 'Ili

+2

Brand Name: OluKai
Product Name: Papaku 'Ili
Gender: Men's
Color: Black/Black
Price: $160.00
Rating: 4Rated 4 stars out of 5(176)

Dr. Martens - Church Quad. Color Black Vintage Smooth. On sale for $159.95. MSRP $200.00. 20% off. 3.9 out of 5 stars

Black Dr. Martens Church Quad

Black Dr. Martens Church Quad

Brand Name: Dr. Martens
Product Name: Church Quad
Gender: Unisex
Color: Black Vintage Smooth
Price: $159.95MSRP: $200.0020% OFF
Rating: 4Rated 4 stars out of 5(10)

Propet - Blizzard Mid Lace. Color Black. On sale for $87.96. MSRP $149.99. 41% off. 4.2 out of 5 stars

Black Propet Blizzard Mid Lace

Black Propet Blizzard Mid Lace

+2

Brand Name: Propet
Product Name: Blizzard Mid Lace
Gender: Men's
Color: Black
Price: $87.96MSRP: $149.9941% OFF
Rating: 4Rated 4 stars out of 5(123)

Dr. Martens - Combs Tech II. Color Black. On sale for $105.28. MSRP $120.00. 12% off. 4.8 out of 5 stars

Black Dr. Martens Combs Tech II

Black Dr. Martens Combs Tech II

Brand Name: Dr. Martens
Product Name: Combs Tech II
Gender: Unisex
Color: Black
Price: $105.28MSRP: $120.0012% OFF
Rating: 5Rated 5 stars out of 5(9)

Barbour - Barbour Nimbus Chelsea Welly. Color Black. Low Stock. On sale for $100.00. MSRP $120.00. 17% off.

Low Stock

Black Barbour Barbour Nimbus Chelsea Welly

Black Barbour Barbour Nimbus Chelsea Welly

Brand Name: Barbour
Product Name: Barbour Nimbus Chelsea Welly
Gender: Men's
Color: Black
Price: $100.00MSRP: $120.0017% OFF
Rating

Deer Stags - Argos. Color Black/Blue. On sale for $48.00. MSRP $100.00. 52% off. 3.7 out of 5 stars

Black Deer Stags Argos

Black Deer Stags Argos

+2

Brand Name: Deer Stags
Product Name: Argos
Gender: Men's
Color: Black/Blue
Price: $48.00MSRP: $100.0052% OFF
Rating: 4Rated 4 stars out of 5(24)

Stacy Adams - Santos Plain Toe Side Zip Boot. Color Black Leather. On sale for $89.90. MSRP $115.00. 22% off. 4.4 out of 5 stars

Black Stacy Adams Santos Plain Toe Side Zip Boot

Black Stacy Adams Santos Plain Toe Side Zip Boot

Brand Name: Stacy Adams
Product Name: Santos Plain Toe Side Zip Boot
Gender: Men's
Color: Black Leather
Price: $89.90MSRP: $115.0022% OFF
Rating: 4Rated 4 stars out of 5(128)

Dr. Martens - 2976 Lo Chelsea. Color Black. $160.00. 3.0 out of 5 stars

Black Dr. Martens 2976 Lo Chelsea

Black Dr. Martens 2976 Lo Chelsea

+2 colors/patterns

Brand Name: Dr. Martens
Product Name: 2976 Lo Chelsea
Gender: Unisex
Color: Black
Price: $160.00
Rating: 3Rated 3 stars out of 5(1)

Teva - Ellwood Mid. Color Grey/Black. $119.95.

Gray Teva Ellwood Mid

Gray Teva Ellwood Mid

+3

Brand Name: Teva
Product Name: Ellwood Mid
Gender: Men's
Color: Grey/Black
Price: $119.95
Rating

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

Black Rockport Storm Surge Water Proof Plain Toe Boot

Black Rockport Storm Surge Water Proof Plain Toe Boot

+2

Brand Name: Rockport
Product Name: Storm Surge Water Proof Plain Toe Boot
Gender: Men's
Color: Black
Price: $119.95MSRP: $159.9525% OFF
Rating: 3Rated 3 stars out of 5(12)

Carhartt - Frontier Water Resistant Steel Toe Chelsea. Color Brown. $139.99. 4.0 out of 5 stars

Brown Carhartt Frontier Water Resistant Steel Toe Chelsea

Brown Carhartt Frontier Water Resistant Steel Toe Chelsea

Brand Name: Carhartt
Product Name: Frontier Water Resistant Steel Toe Chelsea
Gender: Men's
Color: Brown
Price: $139.99
Rating: 4Rated 4 stars out of 5(7)

Tommy Hilfiger - Sesame. Color Black. On sale for $89.99. MSRP $119.00. 24% off. 5.0 out of 5 stars

Black Tommy Hilfiger Sesame

Black Tommy Hilfiger Sesame

+2

Brand Name: Tommy Hilfiger
Product Name: Sesame
Gender: Men's
Color: Black
Price: $89.99MSRP: $119.0024% OFF
Rating: 5Rated 5 stars out of 5(2)

Birkenstock - Highwood Deep Blue. Color Graphite. $200.00. 3.2 out of 5 stars

Gray Birkenstock Highwood Deep Blue

Gray Birkenstock Highwood Deep Blue

+3

Brand Name: Birkenstock
Product Name: Highwood Deep Blue
Gender: Men's
Color: Graphite
Price: $200.00
Rating: 3Rated 3 stars out of 5(4)

Steve Madden - Palta. Color Sand. On sale for $117.00. MSRP $130.00. 10% off.

Beige Steve Madden Palta

Beige Steve Madden Palta

+2

Brand Name: Steve Madden
Product Name: Palta
Gender: Men's
Color: Sand
Price: $117.00MSRP: $130.0010% OFF
Rating

Rockport - Northfield Waterproof Boot. Color Black. On sale for $119.95. MSRP $159.95. 25% off. 4.3 out of 5 stars

Black Rockport Northfield Waterproof Boot

Black Rockport Northfield Waterproof Boot

+2

Brand Name: Rockport
Product Name: Northfield Waterproof Boot
Gender: Men's
Color: Black
Price: $119.95MSRP: $159.9525% OFF
Rating: 4Rated 4 stars out of 5(211)

Carhartt - Plain Toe Wedge Chukka. Color Dark Brown. $139.99. 3.0 out of 5 stars

Brown Carhartt Plain Toe Wedge Chukka

Brown Carhartt Plain Toe Wedge Chukka

Brand Name: Carhartt
Product Name: Plain Toe Wedge Chukka
Gender: Men's
Color: Dark Brown
Price: $139.99
Rating: 3Rated 3 stars out of 5(1)

Propet - Traverse. Color Grey/Black. On sale for $69.97. MSRP $129.99. 46% off. 3.3 out of 5 stars

Gray Propet Traverse

Gray Propet Traverse

+1

Brand Name: Propet
Product Name: Traverse
Gender: Men's
Color: Grey/Black
Price: $69.97MSRP: $129.9946% OFF
Rating: 3Rated 3 stars out of 5(23)

SKECHERS - Relaxed Fit Segment - Melego. Color Dark Brown. On sale for $92.65. MSRP $102.95. 10% off. 4.4 out of 5 stars

Brown SKECHERS Relaxed Fit Segment - Melego

Brown SKECHERS Relaxed Fit Segment - Melego

Brand Name: SKECHERS
Product Name: Relaxed Fit Segment - Melego
Gender: Men's
Color: Dark Brown
Price: $92.65MSRP: $102.9510% OFF
Rating: 4Rated 4 stars out of 5(191)

Steve Madden - Highline. Color Taupe Suede. On sale for $99.99. MSRP $109.95. 9% off. 4.2 out of 5 stars

Taupe Steve Madden Highline

Taupe Steve Madden Highline

+5

Brand Name: Steve Madden
Product Name: Highline
Gender: Men's
Color: Taupe Suede
Price: $99.99MSRP: $109.959% OFF
Rating: 4Rated 4 stars out of 5(22)

Orthofeet - Highline. Color Black. On sale for $97.46. MSRP $149.95. 35% off. 5.0 out of 5 stars

Black Orthofeet Highline

Black Orthofeet Highline

+2 colors/patterns

Brand Name: Orthofeet
Product Name: Highline
Gender: Men's
Color: Black
Price: $97.46MSRP: $149.9535% OFF
Rating: 5Rated 5 stars out of 5(3)

1 of 4

12 3 4Next Page

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.)