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

Men's Size 8.5 M Size Ankle Products

133 items found

Sort By

Your Selections

Search Results

SKECHERS Work - Burgin - Sosder. Color Brown. On sale for $63.99. MSRP $75.00. 15% off. 3.7 out of 5 stars

Brown SKECHERS Work Burgin - Sosder

Brown SKECHERS Work Burgin - Sosder

Brand Name: SKECHERS Work
Product Name: Burgin - Sosder
Gender: Men's
Color: Brown
Price: $63.99MSRP: $75.0015% OFF
Rating: 4Rated 4 stars out of 5(591)

SKECHERS Work - Wascana - Baylan Comp Toe Boots. Color Camel. $85.00. 3.8 out of 5 stars

Tan SKECHERS Work Wascana - Baylan Comp Toe Boots

Tan SKECHERS Work Wascana - Baylan Comp Toe Boots

+2 colors/patterns

Brand Name: SKECHERS Work
Product Name: Wascana - Baylan Comp Toe Boots
Gender: Men's
Color: Camel
Price: $85.00
Rating: 4Rated 4 stars out of 5(12)

Columbia - Newton Ridge Plus II Waterproof. Color Cordovan/Squash. $100.00. 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: $100.00
Rating: 4Rated 4 stars out of 5(1328)

. Columbia - Crestwood Mid Waterproof. Color Dark Grey/Deep Rust. $90.00. 4.1 out of 5 stars

Gray Columbia Crestwood Mid Waterproof

Gray Columbia Crestwood Mid Waterproof

+4

Brand Name: Columbia
Product Name: Crestwood Mid Waterproof
Gender: Men's
Color: Dark Grey/Deep Rust
Price: $90.00
Rating: 4Rated 4 stars out of 5(203)

Columbia - Transverse™ Hike Waterproof. Color Black/Mountain Red. $80.00. 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: Black/Mountain Red
Price: $80.00
Rating: 4Rated 4 stars out of 5(112)

Danner - Traverser 600. Color Jet Black. On sale for $91.77. MSRP $179.95. 49% off. 5.0 out of 5 stars

Black Danner Traverser 600

Black Danner Traverser 600

+2

Brand Name: Danner
Product Name: Traverser 600
Gender: Men's
Color: Jet Black
Price: $91.77MSRP: $179.9549% OFF
Rating: 5Rated 5 stars out of 5(1)

Columbia - Newton Wander Leather. Color Black/Grill. $100.00. 5.0 out of 5 stars

Black Columbia Newton Wander Leather

Black Columbia Newton Wander Leather

+4

Brand Name: Columbia
Product Name: Newton Wander Leather
Gender: Men's
Color: Black/Grill
Price: $100.00
Rating: 5Rated 5 stars out of 5(1)

Stacy Adams - Maury Cap Toe Chelsea Boot. Color Black. On sale for $78.00. MSRP $125.00. 38% 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: $78.00MSRP: $125.0038% OFF
Rating: 5Rated 5 stars out of 5(41)

Nunn Bush - Otis 2.0 Chelsea Fashion Leather Boot. Color Brown. On sale for $79.95. MSRP $109.95. 27% off. 4.2 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: $79.95MSRP: $109.9527% OFF
Rating: 4Rated 4 stars out of 5(6)

Nunn Bush - Ozark 2.0 Plain Toe Chukka Leather Boot. Color Black. On sale for $68.70. MSRP $109.95. 38% off. 4.5 out of 5 stars

Black Nunn Bush Ozark 2.0 Plain Toe Chukka Leather Boot

Black 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: Black
Price: $68.70MSRP: $109.9538% OFF
Rating: 5Rated 5 stars out of 5(6)

Dockers - Esmond. Color Dark Brown. On sale for $51.00. MSRP $85.00. 40% off.

Brown Dockers Esmond

Brown Dockers Esmond

+4

Brand Name: Dockers
Product Name: Esmond
Gender: Men's
Color: Dark Brown
Price: $51.00MSRP: $85.0040% OFF
Rating

Eastland 1955 Edition - Norway. Color Oak. On sale for $87.50. MSRP $125.00. 30% off.

Brown Eastland 1955 Edition Norway

Brown Eastland 1955 Edition Norway

+2

Brand Name: Eastland 1955 Edition
Product Name: Norway
Gender: Men's
Color: Oak
Price: $87.50MSRP: $125.0030% OFF
Rating

Nunn Bush - Chase Plain Toe Chukka Contemporary Fashion Boot. Color Cognac. On sale for $53.99. MSRP $90.00. 40% off. 4.1 out of 5 stars

Tan Nunn Bush Chase Plain Toe Chukka Contemporary Fashion Boot

Tan 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: Cognac
Price: $53.99MSRP: $90.0040% OFF
Rating: 4Rated 4 stars out of 5(13)

Airwalk Work - Arena Mid Comp Toe EH SR. Color Olive/Black. On sale for $79.99. MSRP $124.99. 36% off. 3.3 out of 5 stars

Black Airwalk Work Arena Mid Comp Toe EH SR

Black Airwalk Work Arena Mid Comp Toe EH SR

+4

Brand Name: Airwalk Work
Product Name: Arena Mid Comp Toe EH SR
Gender: Men's
Color: Olive/Black
Price: $79.99MSRP: $124.9936% OFF
Rating: 3Rated 3 stars out of 5(29)

Nunn Bush - Odell 2.0 Wingtip Dress Casual Chukka Leather Boot. Color Black. On sale for $79.95. MSRP $109.95. 27% off. 4.5 out of 5 stars

Black Nunn Bush Odell 2.0 Wingtip Dress Casual Chukka Leather Boot

Black 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: Black
Price: $79.95MSRP: $109.9527% OFF
Rating: 5Rated 5 stars out of 5(8)

Rockport - Northfield Waterproof Boot. Color Black. On sale for $89.95. MSRP $140.00. 36% 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: $89.95MSRP: $140.0036% OFF
Rating: 4Rated 4 stars out of 5(207)

SKECHERS Work - Delson 3.0 SR - Tyoll Comp Toe. Color Brown. $95.00. 2.8 out of 5 stars

Brown SKECHERS Work Delson 3.0 SR - Tyoll Comp Toe

Brown 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: Brown
Price: $95.00
Rating: 3Rated 3 stars out of 5(4)

Clarks - Shacre Boot. Color Dark Sand Suede. On sale for $71.40. MSRP $110.00. 35% 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: Dark Sand Suede
Price: $71.40MSRP: $110.0035% OFF
Rating: 4Rated 4 stars out of 5(67)

Clarks - Shepton. Color Taupe Distressed Leather. On sale for $61.96. MSRP $100.00. 38% off. 2.0 out of 5 stars

Taupe Clarks Shepton

Taupe Clarks Shepton

+5

Brand Name: Clarks
Product Name: Shepton
Gender: Men's
Color: Taupe Distressed Leather
Price: $61.96MSRP: $100.0038% OFF
Rating: 2Rated 2 stars out of 5(4)

Tommy Hilfiger - Rosell. Color Medium Brown. On sale for $73.37. MSRP $79.95. 8% off.

Brown Tommy Hilfiger Rosell

Brown Tommy Hilfiger Rosell

+1

Brand Name: Tommy Hilfiger
Product Name: Rosell
Gender: Men's
Color: Medium Brown
Price: $73.37MSRP: $79.958% OFF
Rating

Steve Madden - Jotting. Color Dark Tan Leather. $99.95.

Brown Steve Madden Jotting

Brown Steve Madden Jotting

+2

Brand Name: Steve Madden
Product Name: Jotting
Gender: Men's
Color: Dark Tan Leather
Price: $99.95
Rating

Nunn Bush - Circuit DC Plain Toe Chukka. Color Brown. On sale for $59.95. MSRP $85.00. 29% off. 3.8 out of 5 stars

Brown Nunn Bush Circuit DC Plain Toe Chukka

Brown Nunn Bush Circuit DC Plain Toe Chukka

+3

Brand Name: Nunn Bush
Product Name: Circuit DC Plain Toe Chukka
Gender: Men's
Color: Brown
Price: $59.95MSRP: $85.0029% OFF
Rating: 4Rated 4 stars out of 5(48)

Tommy Hilfiger - Sesame. Color Black. On sale for $79.99. MSRP $109.00. 27% 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: $79.99MSRP: $109.0027% OFF
Rating: 5Rated 5 stars out of 5(2)

. Steve Madden - Highline. Color Tobacco Suede. $99.95. 4.2 out of 5 stars

Brown Steve Madden Highline

Brown Steve Madden Highline

+5

Brand Name: Steve Madden
Product Name: Highline
Gender: Men's
Color: Tobacco Suede
Price: $99.95
Rating: 4Rated 4 stars out of 5(22)

Tommy Hilfiger - Bage. Color Cognac Tumble. On sale for $74.08. MSRP $109.00. 32% off. 5.0 out of 5 stars

Tan Tommy Hilfiger Bage

Tan Tommy Hilfiger Bage

+3

Brand Name: Tommy Hilfiger
Product Name: Bage
Gender: Men's
Color: Cognac Tumble
Price: $74.08MSRP: $109.0032% OFF
Rating: 5Rated 5 stars out of 5(1)

Nunn Bush - Denali Plain Toe Chukka. Color Black. On sale for $84.95. MSRP $115.00. 26% 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: $84.95MSRP: $115.0026% OFF
Rating: 4Rated 4 stars out of 5(100)

Rockport - Rugged Bucks Waterproof Boot. Color Boston Tan. On sale for $99.95. MSRP $140.00. 29% off. 3.9 out of 5 stars

Brown Rockport Rugged Bucks Waterproof Boot

Brown Rockport Rugged Bucks Waterproof Boot

+2

Brand Name: Rockport
Product Name: Rugged Bucks Waterproof Boot
Gender: Men's
Color: Boston Tan
Price: $99.95MSRP: $140.0029% OFF
Rating: 4Rated 4 stars out of 5(175)

Orthofeet - Hunter. Color Brown. Low Stock. On sale for $79.72. MSRP $144.95. 45% off. 4.2 out of 5 stars

Low Stock

Brown Orthofeet Hunter

Brown Orthofeet Hunter

Brand Name: Orthofeet
Product Name: Hunter
Gender: Men's
Color: Brown
Price: $79.72MSRP: $144.9545% OFF
Rating: 4Rated 4 stars out of 5(5)

Eastland 1955 Edition - Jason. Color Black. On sale for $75.60. MSRP $90.00. 16% off.

Black Eastland 1955 Edition Jason

Black Eastland 1955 Edition Jason

+3

Brand Name: Eastland 1955 Edition
Product Name: Jason
Gender: Men's
Color: Black
Price: $75.60MSRP: $90.0016% OFF
Rating

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)

Nunn Bush - Otto Plain Toe Chukka Boot. Color Black. On sale for $79.95. MSRP $110.00. 27% off. 4.0 out of 5 stars

Black Nunn Bush Otto Plain Toe Chukka Boot

Black Nunn Bush Otto Plain Toe Chukka Boot

+3

Brand Name: Nunn Bush
Product Name: Otto Plain Toe Chukka Boot
Gender: Men's
Color: Black
Price: $79.95MSRP: $110.0027% OFF
Rating: 4Rated 4 stars out of 5(24)

Sperry - Cold Bay Chelsea. Color Black. $99.95. 3.0 out of 5 stars

Black Sperry Cold Bay Chelsea

Black Sperry Cold Bay Chelsea

+2

Brand Name: Sperry
Product Name: Cold Bay Chelsea
Gender: Men's
Color: Black
Price: $99.95
Rating: 3Rated 3 stars out of 5(1)

Columbia - Newton Ridge™ BC. Color Ash Brown/Waterfall. On sale for $85.46. MSRP $100.00. 15% off. 3.9 out of 5 stars

Brown Columbia Newton Ridge™ BC

Brown Columbia Newton Ridge™ BC

+2

Brand Name: Columbia
Product Name: Newton Ridge™ BC
Gender: Men's
Color: Ash Brown/Waterfall
Price: $85.46MSRP: $100.0015% OFF
Rating: 4Rated 4 stars out of 5(23)

Propet - Ridge Walker. Color Black. On sale for $91.96. MSRP $114.95. 20% off. 4.0 out of 5 stars

Black Propet Ridge Walker

Black Propet Ridge Walker

+4

Brand Name: Propet
Product Name: Ridge Walker
Gender: Men's
Color: Black
Price: $91.96MSRP: $114.9520% OFF
Rating: 4Rated 4 stars out of 5(198)

adidas Outdoor - Terrex Trailmaker 2 Leather Hiking Shoes. Color Olive Strata/Olive Strata/Silver Pebble. On sale for $97.46. MSRP $130.00. 25% off. 4.4 out of 5 stars

Olive adidas Outdoor Terrex Trailmaker 2 Leather Hiking Shoes

Olive adidas Outdoor Terrex Trailmaker 2 Leather Hiking Shoes

+3

Brand Name: adidas Outdoor
Product Name: Terrex Trailmaker 2 Leather Hiking Shoes
Gender: Men's
Color: Olive Strata/Olive Strata/Silver Pebble
Price: $97.46MSRP: $130.0025% OFF
Rating: 4Rated 4 stars out of 5(18)

Columbia - Strata Trail™ Mid Wp. Color Black/Owl. $90.00.

Black Columbia Strata Trail™ Mid Wp

Black Columbia Strata Trail™ Mid Wp

+2

Brand Name: Columbia
Product Name: Strata Trail™ Mid Wp
Gender: Men's
Color: Black/Owl
Price: $90.00
Rating

SKECHERS - Relaxed Fit Respected - Boswell. Color Dark Brown. On sale for $70.00. MSRP $97.95. 29% off. 4.2 out of 5 stars

Brown SKECHERS Relaxed Fit Respected - Boswell

Brown SKECHERS Relaxed Fit Respected - Boswell

Brand Name: SKECHERS
Product Name: Relaxed Fit Respected - Boswell
Gender: Men's
Color: Dark Brown
Price: $70.00MSRP: $97.9529% OFF
Rating: 4Rated 4 stars out of 5(199)

Deer Stags - Rockland. Color Brown/Dark Brown. On sale for $34.99. MSRP $90.00. 61% off. 3.6 out of 5 stars

Brown Deer Stags Rockland

Brown Deer Stags Rockland

+1

Brand Name: Deer Stags
Product Name: Rockland
Gender: Men's
Color: Brown/Dark Brown
Price: $34.99MSRP: $90.0061% OFF
Rating: 4Rated 4 stars out of 5(30)

Oboz - Burke Mid Leather B-Dry. Color Granite. On sale for $94.05. MSRP $165.00. 43% off. 4.0 out of 5 stars

Gray Oboz Burke Mid Leather B-Dry

Gray Oboz Burke Mid Leather B-Dry

+5

Brand Name: Oboz
Product Name: Burke Mid Leather B-Dry
Gender: Men's
Color: Granite
Price: $94.05MSRP: $165.0043% OFF
Rating: 4Rated 4 stars out of 5(20)

Clarks - Shepton Easy. Color Black Leather. On sale for $81.56. MSRP $120.00. 32% off.

Black Clarks Shepton Easy

Black Clarks Shepton Easy

+2

Brand Name: Clarks
Product Name: Shepton Easy
Gender: Men's
Color: Black Leather
Price: $81.56MSRP: $120.0032% OFF
Rating

Timberland - Motion Access. Color Light Taupe Knit. On sale for $94.97. MSRP $120.00. 21% off. 4.3 out of 5 stars

Taupe Timberland Motion Access

Taupe Timberland Motion Access

+4

Brand Name: Timberland
Product Name: Motion Access
Gender: Men's
Color: Light Taupe Knit
Price: $94.97MSRP: $120.0021% OFF
Rating: 4Rated 4 stars out of 5(52)

Wolverine - Trade Wedge Waterproof Steel Toe Romeo. Color Sudan Brown. Low Stock. On sale for $83.97. MSRP $125.00. 33% off. 4.0 out of 5 stars

Low Stock

Brown Wolverine Trade Wedge Waterproof Steel Toe Romeo

Brown Wolverine Trade Wedge Waterproof Steel Toe Romeo

Brand Name: Wolverine
Product Name: Trade Wedge Waterproof Steel Toe Romeo
Gender: Men's
Color: Sudan Brown
Price: $83.97MSRP: $125.0033% OFF
Rating: 4Rated 4 stars out of 5(1)

Eastland 1955 Edition - Lumber Up. Color Peanut Leather. On sale for $81.90. MSRP $135.00. 39% off. 4.2 out of 5 stars

Tan Eastland 1955 Edition Lumber Up

Tan Eastland 1955 Edition Lumber Up

+8

Brand Name: Eastland 1955 Edition
Product Name: Lumber Up
Gender: Men's
Color: Peanut Leather
Price: $81.90MSRP: $135.0039% OFF
Rating: 4Rated 4 stars out of 5(52)

Rockport - Storm Surge Water Proof Plain Toe Boot. Color Tan. On sale for $99.95. MSRP $139.95. 29% off. 3.3 out of 5 stars

Tan Rockport Storm Surge Water Proof Plain Toe Boot

Tan 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: Tan
Price: $99.95MSRP: $139.9529% OFF
Rating: 3Rated 3 stars out of 5(12)

Steve Madden - Duke. Color Cognac Leather. On sale for $98.00. MSRP $140.00. 30% off. 5.0 out of 5 stars

Brown Steve Madden Duke

Brown Steve Madden Duke

Brand Name: Steve Madden
Product Name: Duke
Gender: Men's
Color: Cognac Leather
Price: $98.00MSRP: $140.0030% OFF
Rating: 5Rated 5 stars out of 5(1)

Wolverine - Carlsbad Waterproof 6" Steel Toe Work Boot. Color Black. On sale for $99.95. MSRP $110.00. 9% off. 3.5 out of 5 stars

Black Wolverine Carlsbad Waterproof 6" Steel Toe Work Boot

Black Wolverine Carlsbad Waterproof 6" Steel Toe Work Boot

Brand Name: Wolverine
Product Name: Carlsbad Waterproof 6" Steel Toe Work Boot
Gender: Men's
Color: Black
Price: $99.95MSRP: $110.009% OFF
Rating: 4Rated 4 stars out of 5(27)

Caterpillar - Outline ST. Color Dark Gull Grey. $99.95. 3.5 out of 5 stars

Gray Caterpillar Outline ST

Gray Caterpillar Outline ST

+2

Brand Name: Caterpillar
Product Name: Outline ST
Gender: Men's
Color: Dark Gull Grey
Price: $99.95
Rating: 3Rated 3 stars out of 5(28)

Hoss - Watchman 6" Composite Toe - BIG HOSS Sizes. Color Black. $99.95. 3.8 out of 5 stars

Black Hoss Watchman 6" Composite Toe - BIG HOSS Sizes

Black Hoss Watchman 6" Composite Toe - BIG HOSS Sizes

Brand Name: Hoss
Product Name: Watchman 6" Composite Toe - BIG HOSS Sizes
Gender: Men's
Color: Black
Price: $99.95
Rating: 4Rated 4 stars out of 5(21)

Dockers - Rockford. Color Dark Tan. On sale for $49.99. MSRP $85.00. 41% off. 5.0 out of 5 stars

Brown Dockers Rockford

Brown Dockers Rockford

+3

Brand Name: Dockers
Product Name: Rockford
Gender: Men's
Color: Dark Tan
Price: $49.99MSRP: $85.0041% OFF
Rating: 5Rated 5 stars out of 5(2)

Nunn Bush - Otis Plain Toe Chelsea Boot with KORE Walking Comfort Technology. Color Black Tumbled. On sale for $95.45. MSRP $115.00. 17% off. 4.2 out of 5 stars

Black Nunn Bush Otis Plain Toe Chelsea Boot with KORE Walking Comfort Technology

Black Nunn Bush Otis Plain Toe Chelsea Boot with KORE Walking Comfort Technology

+3

Brand Name: Nunn Bush
Product Name: Otis Plain Toe Chelsea Boot with KORE Walking Comfort Technology
Gender: Men's
Color: Black Tumbled
Price: $95.45MSRP: $115.0017% OFF
Rating: 4Rated 4 stars out of 5(102)

Florsheim - Renegade Cap Toe Boot. Color Cognac. On sale for $88.60. MSRP $150.00. 41% off. 4.1 out of 5 stars

Tan Florsheim Renegade Cap Toe Boot

Tan Florsheim Renegade Cap Toe Boot

+1

Brand Name: Florsheim
Product Name: Renegade Cap Toe Boot
Gender: Men's
Color: Cognac
Price: $88.60MSRP: $150.0041% OFF
Rating: 4Rated 4 stars out of 5(29)

. Steve Madden - Hestonn. Color Tobacco Suede. On sale for $80.45. MSRP $90.00. 11% off. 3.8 out of 5 stars

Brown Steve Madden Hestonn

Brown Steve Madden Hestonn

+2

Brand Name: Steve Madden
Product Name: Hestonn
Gender: Men's
Color: Tobacco Suede
Price: $80.45MSRP: $90.0011% OFF
Rating: 4Rated 4 stars out of 5(73)

Rockport - Classic Break Chukka. Color Dark Brown Leather. On sale for $98.00. MSRP $139.95. 30% 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: $98.00MSRP: $139.9530% OFF
Rating: 4Rated 4 stars out of 5(212)

Carhartt - Haslett Moc Toe Canvas Chukka. Color Brown Lightweight Durable Canvas. $99.99. 3.9 out of 5 stars

Beige Carhartt Haslett Moc Toe Canvas Chukka

Beige Carhartt Haslett Moc Toe Canvas Chukka

+3

Brand Name: Carhartt
Product Name: Haslett Moc Toe Canvas Chukka
Gender: Men's
Color: Brown Lightweight Durable Canvas
Price: $99.99
Rating: 4Rated 4 stars out of 5(33)

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)

Eastland 1955 Edition - Cyrus. Color Brown. On sale for $71.99. MSRP $90.00. 20% off. 1.0 out of 5 stars

Brown Eastland 1955 Edition Cyrus

Brown Eastland 1955 Edition Cyrus

+2 colors/patterns

Brand Name: Eastland 1955 Edition
Product Name: Cyrus
Gender: Men's
Color: Brown
Price: $71.99MSRP: $90.0020% OFF
Rating: 1Rated 1 star out of 5(1)

Eastland 1955 Edition - Jack. Color Brown. Low Stock. On sale for $87.50. MSRP $125.00. 30% off. 4.2 out of 5 stars

Low Stock

Brown Eastland 1955 Edition Jack

Brown Eastland 1955 Edition Jack

+2

Brand Name: Eastland 1955 Edition
Product Name: Jack
Gender: Men's
Color: Brown
Price: $87.50MSRP: $125.0030% OFF
Rating: 4Rated 4 stars out of 5(8)

SKECHERS Work - Wascana - Benen WP Tactical. Color Black. On sale for $83.00. MSRP $85.00. 2% off. 3.8 out of 5 stars

Black SKECHERS Work Wascana - Benen WP Tactical

Black SKECHERS Work Wascana - Benen WP Tactical

Brand Name: SKECHERS Work
Product Name: Wascana - Benen WP Tactical
Gender: Men's
Color: Black
Price: $83.00MSRP: $85.002% OFF
Rating: 4Rated 4 stars out of 5(303)

Dr. Scholl's - Manchester. Color Grey Faux Leather. On sale for $78.20. MSRP $120.00. 35% off. 3.0 out of 5 stars

Gray Dr. Scholl's Manchester

Gray Dr. Scholl's Manchester

+3

Brand Name: Dr. Scholl's
Product Name: Manchester
Gender: Men's
Color: Grey Faux Leather
Price: $78.20MSRP: $120.0035% OFF
Rating: 3Rated 3 stars out of 5(2)

Steve Madden - Montreaux. Color Tan. On sale for $93.60. MSRP $130.00. 28% off.

Tan Steve Madden Montreaux

Tan Steve Madden Montreaux

Brand Name: Steve Madden
Product Name: Montreaux
Gender: Men's
Color: Tan
Price: $93.60MSRP: $130.0028% OFF
Rating

Propet - Cliff Walker Medicare/HCPCS Code = A5500 Diabetic Shoe. Color Bronco Brown. On sale for $91.96. MSRP $129.95. 29% off. 4.3 out of 5 stars

Brown Propet Cliff Walker Medicare/HCPCS Code = A5500 Diabetic Shoe

Brown Propet Cliff Walker Medicare/HCPCS Code = A5500 Diabetic Shoe

+2 colors/patterns

Brand Name: Propet
Product Name: Cliff Walker Medicare/HCPCS Code = A5500 Diabetic Shoe
Gender: Men's
Color: Bronco Brown
Price: $91.96MSRP: $129.9529% OFF
Rating: 4Rated 4 stars out of 5(255)

Eastland 1955 Edition - Herman. Color Brown. On sale for $89.99. MSRP $135.00. 33% off.

Brown Eastland 1955 Edition Herman

Brown Eastland 1955 Edition Herman

+3

Brand Name: Eastland 1955 Edition
Product Name: Herman
Gender: Men's
Color: Brown
Price: $89.99MSRP: $135.0033% OFF
Rating

Steve Madden - Jotter. Color Dark Tan. $100.00. 4.4 out of 5 stars

Brown Steve Madden Jotter

Brown Steve Madden Jotter

+2

Brand Name: Steve Madden
Product Name: Jotter
Gender: Men's
Color: Dark Tan
Price: $100.00
Rating: 4Rated 4 stars out of 5(23)

Nunn Bush - Karnak Moc Toe Boot Lightweight Comfortable Chukka. Color Black. On sale for $79.95. MSRP $109.95. 27% off. 4.6 out of 5 stars

Black Nunn Bush Karnak Moc Toe Boot Lightweight Comfortable Chukka

Black 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: Black
Price: $79.95MSRP: $109.9527% OFF
Rating: 5Rated 5 stars out of 5(9)

Marc Joseph New York - Chicago. Color Black Grainy. Low Stock. On sale for $89.95. MSRP $195.00. 54% off. 3.0 out of 5 stars

Low Stock

Black Marc Joseph New York Chicago

Black Marc Joseph New York Chicago

Brand Name: Marc Joseph New York
Product Name: Chicago
Gender: Men's
Color: Black Grainy
Price: $89.95MSRP: $195.0054% OFF
Rating: 3Rated 3 stars out of 5(2)

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)

Florsheim - Renegade Plain Toe Chukka Boot. Color Brown Crazy Horse. On sale for $87.00. MSRP $150.00. 42% off. 4.4 out of 5 stars

Brown Florsheim Renegade Plain Toe Chukka Boot

Brown Florsheim Renegade Plain Toe Chukka Boot

Brand Name: Florsheim
Product Name: Renegade Plain Toe Chukka Boot
Gender: Men's
Color: Brown Crazy Horse
Price: $87.00MSRP: $150.0042% OFF
Rating: 4Rated 4 stars out of 5(34)

SKECHERS Work - Wascana - Linnean Comp Toe. Color Black. $95.00. 4.0 out of 5 stars

Black SKECHERS Work Wascana - Linnean Comp Toe

Black SKECHERS Work Wascana - Linnean Comp Toe

Brand Name: SKECHERS Work
Product Name: Wascana - Linnean Comp Toe
Gender: Men's
Color: Black
Price: $95.00
Rating: 4Rated 4 stars out of 5(132)

Stacy Adams - Gabriel Chelsea Boot. Color Sand Suede. On sale for $94.95. MSRP $120.00. 21% off. 4.7 out of 5 stars

Tan Stacy Adams Gabriel Chelsea Boot

Tan Stacy Adams Gabriel Chelsea Boot

+3

Brand Name: Stacy Adams
Product Name: Gabriel Chelsea Boot
Gender: Men's
Color: Sand Suede
Price: $94.95MSRP: $120.0021% OFF
Rating: 5Rated 5 stars out of 5(9)

Carhartt - 6" Rugged Flex Steel Toe. Color Dark Brown Leather/Synthetic. $99.99. 3.9 out of 5 stars

Brown Carhartt 6" Rugged Flex Steel Toe

Brown Carhartt 6" Rugged Flex Steel Toe

Brand Name: Carhartt
Product Name: 6" Rugged Flex Steel Toe
Gender: Men's
Color: Dark Brown Leather/Synthetic
Price: $99.99
Rating: 4Rated 4 stars out of 5(93)

Rockport - Evan Waterproof Boots. Color Dark Taupe Multi. On sale for $90.13. 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: $90.13MSRP: $149.9540% OFF
Rating: 4Rated 4 stars out of 5(2)

Eastland 1955 Edition - Finn. Color Tan. On sale for $82.37. MSRP $90.00. 8% 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: $82.37MSRP: $90.008% OFF
Rating

Rockport - Seamus. Color Dark Brown Suede. On sale for $89.99. MSRP $149.95. 40% off.

Brown Rockport Seamus

Brown Rockport Seamus

+4

Brand Name: Rockport
Product Name: Seamus
Gender: Men's
Color: Dark Brown Suede
Price: $89.99MSRP: $149.9540% OFF
Rating

Deer Stags - Brayden. Color Black. On sale for $52.00. MSRP $100.00. 48% off. 3.0 out of 5 stars

Black Deer Stags Brayden

Black Deer Stags Brayden

+2

Brand Name: Deer Stags
Product Name: Brayden
Gender: Men's
Color: Black
Price: $52.00MSRP: $100.0048% OFF
Rating: 3Rated 3 stars out of 5(1)

Original S.W.A.T. - ProTec 6" Side Zip Polishable Toe Boot. Color Black. On sale for $75.00. MSRP $85.00. 12% off. 1.8 out of 5 stars

Black Original S.W.A.T. ProTec 6" Side Zip Polishable Toe Boot

Black Original S.W.A.T. ProTec 6" Side Zip Polishable Toe Boot

Brand Name: Original S.W.A.T.
Product Name: ProTec 6" Side Zip Polishable Toe Boot
Gender: Unisex
Color: Black
Price: $75.00MSRP: $85.0012% OFF
Rating: 2Rated 2 stars out of 5(5)

Eastland 1955 Edition - Lace Up Boots. Color Oak. On sale for $94.50. MSRP $135.00. 30% off. 3.6 out of 5 stars

Brown Eastland 1955 Edition Lace Up Boots

Brown Eastland 1955 Edition Lace Up Boots

+5

Brand Name: Eastland 1955 Edition
Product Name: Lace Up Boots
Gender: Men's
Color: Oak
Price: $94.50MSRP: $135.0030% OFF
Rating: 4Rated 4 stars out of 5(13)

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

+1

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)

L.L.Bean - Rubber Moc. Color Tan/Bean Boot Brown/Gum. On sale for $99.00. MSRP $119.00. 17% off. 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: $99.00MSRP: $119.0017% OFF
Rating: 4Rated 4 stars out of 5(20)

Dockers - Norton. Color Dark Tan. Low Stock. On sale for $49.99. MSRP $85.00. 41% off. 2.6 out of 5 stars

Low Stock

Brown Dockers Norton

Brown Dockers Norton

+3

Brand Name: Dockers
Product Name: Norton
Gender: Men's
Color: Dark Tan
Price: $49.99MSRP: $85.0041% OFF
Rating: 3Rated 3 stars out of 5(5)

Dockers - Dudley. Color Black. On sale for $49.99. MSRP $85.00. 41% off. 3.3 out of 5 stars

Black Dockers Dudley

Black Dockers Dudley

+2

Brand Name: Dockers
Product Name: Dudley
Gender: Men's
Color: Black
Price: $49.99MSRP: $85.0041% OFF
Rating: 3Rated 3 stars out of 5(3)

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

Black Deer Stags Bangor

Black Deer Stags Bangor

+2

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

SKECHERS Work - Watab - Shred - Shield Comp Toe. Color Black. $100.00. 3.0 out of 5 stars

Black SKECHERS Work Watab - Shred - Shield Comp Toe

Black SKECHERS Work Watab - Shred - Shield Comp Toe

+3

Brand Name: SKECHERS Work
Product Name: Watab - Shred - Shield Comp Toe
Gender: Men's
Color: Black
Price: $100.00
Rating: 3Rated 3 stars out of 5(1)

L.L.Bean - Stonington Boot Moc Toe Suede. Color Deepest Brown. On sale for $78.97. MSRP $149.00. 47% 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: $78.97MSRP: $149.0047% OFF
Rating: 5Rated 5 stars out of 5(1)

Caterpillar - Striver Waterproof Steel Toe. Color Brown 1. $99.95. 4.0 out of 5 stars

Brown Caterpillar Striver Waterproof Steel Toe

Brown Caterpillar Striver Waterproof Steel Toe

Brand Name: Caterpillar
Product Name: Striver Waterproof Steel Toe
Gender: Men's
Color: Brown 1
Price: $99.95
Rating: 4Rated 4 stars out of 5(1)

ACE Work Boots - Defender Mid NCT. Color Black. $94.98. 3.8 out of 5 stars

Black ACE Work Boots Defender Mid NCT

Black ACE Work Boots Defender Mid NCT

Brand Name: ACE Work Boots
Product Name: Defender Mid NCT
Gender: Unisex
Color: Black
Price: $94.98
Rating: 4Rated 4 stars out of 5(29)

Nunn Bush - Odell Wingtip Boot with KORE Walking Comfort Technology. Color Black Tumbled. On sale for $91.98. MSRP $115.00. 20% off. 4.2 out of 5 stars

Black Nunn Bush Odell Wingtip Boot with KORE Walking Comfort Technology

Black Nunn Bush Odell Wingtip Boot with KORE Walking Comfort Technology

+3

Brand Name: Nunn Bush
Product Name: Odell Wingtip Boot with KORE Walking Comfort Technology
Gender: Men's
Color: Black Tumbled
Price: $91.98MSRP: $115.0020% OFF
Rating: 4Rated 4 stars out of 5(127)

Propet - Blizzard Ankle Zip. Color Brown/Black. On sale for $79.96. MSRP $119.95. 33% 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: $79.96MSRP: $119.9533% OFF
Rating: 4Rated 4 stars out of 5(142)

Nunn Bush - Excavate Plain Toe Chukka Boot. Color Brown. On sale for $59.95. MSRP $90.00. 33% off. 4.4 out of 5 stars

Brown Nunn Bush Excavate Plain Toe Chukka Boot

Brown Nunn Bush Excavate Plain Toe Chukka Boot

+1

Brand Name: Nunn Bush
Product Name: Excavate Plain Toe Chukka Boot
Gender: Men's
Color: Brown
Price: $59.95MSRP: $90.0033% OFF
Rating: 4Rated 4 stars out of 5(23)

Caterpillar - Striver ST. Color Black. $89.95. 4.2 out of 5 stars

Black Caterpillar Striver ST

Black Caterpillar Striver ST

+2

Brand Name: Caterpillar
Product Name: Striver ST
Gender: Men's
Color: Black
Price: $89.95
Rating: 4Rated 4 stars out of 5(4)

Eastland 1955 Edition - Seneca. Color Tan. On sale for $87.99. MSRP $120.00. 27% off. 4.4 out of 5 stars

Tan Eastland 1955 Edition Seneca

Tan Eastland 1955 Edition Seneca

+3

Brand Name: Eastland 1955 Edition
Product Name: Seneca
Gender: Men's
Color: Tan
Price: $87.99MSRP: $120.0027% OFF
Rating: 4Rated 4 stars out of 5(42)

Tommy Hilfiger - Berton. Color Black. On sale for $65.50. MSRP $109.00. 40% off.

Black Tommy Hilfiger Berton

Black Tommy Hilfiger Berton

+2

Brand Name: Tommy Hilfiger
Product Name: Berton
Gender: Men's
Color: Black
Price: $65.50MSRP: $109.0040% OFF
Rating

Propet - Findley. Color Black. On sale for $95.00. MSRP $134.95. 30% off. 3.6 out of 5 stars

Black Propet Findley

Black Propet Findley

+2

Brand Name: Propet
Product Name: Findley
Gender: Men's
Color: Black
Price: $95.00MSRP: $134.9530% OFF
Rating: 4Rated 4 stars out of 5(12)

Propet - Cliff Walker. Color Wheat. On sale for $83.71. MSRP $124.95. 33% 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: $83.71MSRP: $124.9533% OFF
Rating: 4Rated 4 stars out of 5(8)

Florsheim - Forge Plain Toe Lace Boot. Color Black. Low Stock. On sale for $87.51. MSRP $120.00. 27% off. 3.0 out of 5 stars

Low Stock

Black Florsheim Forge Plain Toe Lace Boot

Black Florsheim Forge Plain Toe Lace Boot

+2

Brand Name: Florsheim
Product Name: Forge Plain Toe Lace Boot
Gender: Men's
Color: Black
Price: $87.51MSRP: $120.0027% OFF
Rating: 3Rated 3 stars out of 5(4)

Columbia - Bugaboot III. Color Black/Bright Red 1. On sale for $89.69. MSRP $120.00. 25% off. 4.1 out of 5 stars

Black Columbia Bugaboot III

Black Columbia Bugaboot III

+3

Brand Name: Columbia
Product Name: Bugaboot III
Gender: Men's
Color: Black/Bright Red 1
Price: $89.69MSRP: $120.0025% OFF
Rating: 4Rated 4 stars out of 5(365)

Stacy Adams - Maxwell Plain Toe Demi Boot. Color Cognac. On sale for $79.20. MSRP $125.00. 37% 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: $79.20MSRP: $125.0037% OFF
Rating: 5Rated 5 stars out of 5(43)

Nunn Bush - 1912 Plain Toe Chelsea Boot. Color Black. Low Stock. On sale for $80.50. MSRP $115.00. 30% off. 3.9 out of 5 stars

Low Stock

Black Nunn Bush 1912 Plain Toe Chelsea Boot

Black Nunn Bush 1912 Plain Toe Chelsea Boot

Brand Name: Nunn Bush
Product Name: 1912 Plain Toe Chelsea Boot
Gender: Men's
Color: Black
Price: $80.50MSRP: $115.0030% OFF
Rating: 4Rated 4 stars out of 5(14)

Dockers - Novato. Color Dark Brown. On sale for $69.99. MSRP $95.00. 26% off.

Brown Dockers Novato

Brown Dockers Novato

Brand Name: Dockers
Product Name: Novato
Gender: Men's
Color: Dark Brown
Price: $69.99MSRP: $95.0026% OFF
Rating

SOREL - Carson™ Chelsea Waterproof. Color Brown. On sale for $99.16. MSRP $155.00. 36% off. 1.0 out of 5 stars

Brown SOREL Carson™ Chelsea Waterproof

Brown SOREL Carson™ Chelsea Waterproof

Brand Name: SOREL
Product Name: Carson™ Chelsea Waterproof
Gender: Men's
Color: Brown
Price: $99.16MSRP: $155.0036% OFF
Rating: 1Rated 1 star out of 5(1)

Eastland 1955 Edition - Baxter. Color Black. On sale for $94.50. MSRP $135.00. 30% off.

Black Eastland 1955 Edition Baxter

Black Eastland 1955 Edition Baxter

+2

Brand Name: Eastland 1955 Edition
Product Name: Baxter
Gender: Men's
Color: Black
Price: $94.50MSRP: $135.0030% OFF
Rating

1 of 2

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.)