Winter Wins
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Size 8.5 Medium Size Ankle Elastic Products

50 items found

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Marc Joseph New York - Hudson Yards 2.0 (Hands Free Technology). Color Cognac Napa Leather. On sale for $99.95. MSRP $195.00. 49% off. 5.0 out of 5 stars

Brown Marc Joseph New York Hudson Yards 2.0 (Hands Free Technology)

Brown Marc Joseph New York Hudson Yards 2.0 (Hands Free Technology)

+4

Brand Name: Marc Joseph New York
Product Name: Hudson Yards 2.0 (Hands Free Technology)
Gender: Men's
Color: Cognac Napa Leather
Price: $99.95MSRP: $19549% OFF
Rating: 5Rated 5 stars out of 5(3)

Florsheim - Lodge Plain Toe Gore Boots. Color Chestnut Smooth. $145.00. 4.4 out of 5 stars

Brown Florsheim Lodge Plain Toe Gore Boots

Brown Florsheim Lodge Plain Toe Gore Boots

+3

Brand Name: Florsheim
Product Name: Lodge Plain Toe Gore Boots
Gender: Men's
Color: Chestnut Smooth
Price: $145
Rating: 4Rated 4 stars out of 5(125)

Nunn Bush - Otis 2.0 Chelsea Fashion Leather Boots. Color Tan. On sale for $84.99. MSRP $120.00. 29% off. 4.2 out of 5 stars

Tan Nunn Bush Otis 2.0 Chelsea Fashion Leather Boots

Tan Nunn Bush Otis 2.0 Chelsea Fashion Leather Boots

+3

Brand Name: Nunn Bush
Product Name: Otis 2.0 Chelsea Fashion Leather Boots
Gender: Men's
Color: Tan
Price: $84.99MSRP: $12029% OFF
Rating: 4Rated 4 stars out of 5(11)

Nunn Bush - Karnak Plain Toe Chelsea Boots Lightweight Comfortable Chukka. Color Black. On sale for $89.95. MSRP $120.00. 25% off. 5.0 out of 5 stars

Black Nunn Bush Karnak Plain Toe Chelsea Boots Lightweight Comfortable Chukka

Black Nunn Bush Karnak Plain Toe Chelsea Boots Lightweight Comfortable Chukka

+2

Brand Name: Nunn Bush
Product Name: Karnak Plain Toe Chelsea Boots Lightweight Comfortable Chukka
Gender: Men's
Color: Black
Price: $89.95MSRP: $12025% OFF
Rating: 5Rated 5 stars out of 5(2)

Dansko - Frankie. Color Black Oiled. $179.95. 4.1 out of 5 stars

Black Dansko Frankie

Black Dansko Frankie

+3

Brand Name: Dansko
Product Name: Frankie
Gender: Women's
Color: Black Oiled
Price: $179.95
Rating: 4Rated 4 stars out of 5(308)

. Steve Madden - Highline. Color Tobacco Suede. $109.95. 4.2 out of 5 stars

Brown Steve Madden Highline

Brown Steve Madden Highline

+4

Brand Name: Steve Madden
Product Name: Highline
Gender: Men's
Color: Tobacco Suede
Price: $109.95
Rating: 4Rated 4 stars out of 5(22)

Born - Hemlock. Color Black Full Grain. $145.00. 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: $145
Rating: 4Rated 4 stars out of 5(191)

Blundstone - Original Suede Chelsea Boots. Color Tobacco. $184.95. 5.0 out of 5 stars

Brown Blundstone Original Suede Chelsea Boots

Brown Blundstone Original Suede Chelsea Boots

+2

Brand Name: Blundstone
Product Name: Original Suede Chelsea Boots
Gender: Unisex
Color: Tobacco
Price: $184.95
Rating: 5Rated 5 stars out of 5(1)

Blundstone - BL1615. Color Olive Suede. $184.95. 5.0 out of 5 stars

Olive Blundstone BL1615

Olive Blundstone BL1615

Brand Name: Blundstone
Product Name: BL1615
Gender: Unisex
Color: Olive Suede
Price: $184.95
Rating: 5Rated 5 stars out of 5(3)

Tommy Hilfiger - Sesame. Color Medium Brown Burnished. On sale for $83.30. MSRP $119.00. 30% off. 5.0 out of 5 stars

Brown Tommy Hilfiger Sesame

Brown Tommy Hilfiger Sesame

+2

Brand Name: Tommy Hilfiger
Product Name: Sesame
Gender: Men's
Color: Medium Brown Burnished
Price: $83.30MSRP: $11930% OFF
Rating: 5Rated 5 stars out of 5(6)

KEEN - Anchorage Boots III Waterproof. Color Dark Earth/Mulch. $174.95. 4.0 out of 5 stars

Brown KEEN Anchorage Boots III Waterproof

Brown KEEN Anchorage Boots III Waterproof

Brand Name: KEEN
Product Name: Anchorage Boots III Waterproof
Gender: Men's
Color: Dark Earth/Mulch
Price: $174.95
Rating: 4Rated 4 stars out of 5(390)

Sperry - Clifton Boots. Color Olive. On sale for $104.99. MSRP $110.00. 5% off. 3.0 out of 5 stars

Olive Sperry Clifton Boots

Olive Sperry Clifton Boots

+2

Brand Name: Sperry
Product Name: Clifton Boots
Gender: Men's
Color: Olive
Price: $104.99MSRP: $1105% OFF
Rating: 3Rated 3 stars out of 5(2)

Johnston & Murphy - Calder 175th Chelsea Boots. Color Black Oiled American Full Grain. $175.00.

Black Johnston & Murphy Calder 175th Chelsea Boots

Black Johnston & Murphy Calder 175th Chelsea Boots

Brand Name: Johnston & Murphy
Product Name: Calder 175th Chelsea Boots
Gender: Men's
Color: Black Oiled American Full Grain
Price: $175
Rating

Steve Madden - Merrnie. Color Taupe. $79.99.

Taupe Steve Madden Merrnie

Taupe Steve Madden Merrnie

+2

Brand Name: Steve Madden
Product Name: Merrnie
Gender: Men's
Color: Taupe
Price: $79.99
Rating

Born - Brody. Color Taupe Dist. $150.00. 4.6 out of 5 stars

Taupe Born Brody

Taupe Born Brody

Brand Name: Born
Product Name: Brody
Gender: Men's
Color: Taupe Dist
Price: $150
Rating: 5Rated 5 stars out of 5(29)

Kenneth Cole - Tully Chelsea Boots. Color Black Leather. On sale for $166.45. MSRP $184.95. 10% off.

Black Kenneth Cole Tully Chelsea Boots

Black Kenneth Cole Tully Chelsea Boots

+2

Brand Name: Kenneth Cole
Product Name: Tully Chelsea Boots
Gender: Men's
Color: Black Leather
Price: $166.45MSRP: $184.9510% OFF
Rating

Twisted X - MDMG002. Color Bomber. $144.95. 5.0 out of 5 stars

Bone Twisted X MDMG002

Bone Twisted X MDMG002

Brand Name: Twisted X
Product Name: MDMG002
Gender: Men's
Color: Bomber
Price: $144.95
Rating: 5Rated 5 stars out of 5(1)

Steve Madden - Hatford. Color Dark Taupe. Low Stock. $100.00.

Low Stock

Taupe Steve Madden Hatford

Taupe Steve Madden Hatford

+4

Brand Name: Steve Madden
Product Name: Hatford
Gender: Men's
Color: Dark Taupe
Price: $100
Rating

Marc Joseph New York - Clark Road (Hands Free Technology). Color Black Napa Leather. On sale for $109.95. MSRP $195.00. 44% off. 5.0 out of 5 stars

Black Marc Joseph New York Clark Road (Hands Free Technology)

Black Marc Joseph New York Clark Road (Hands Free Technology)

+4

Brand Name: Marc Joseph New York
Product Name: Clark Road (Hands Free Technology)
Gender: Men's
Color: Black Napa Leather
Price: $109.95MSRP: $19544% OFF
Rating: 5Rated 5 stars out of 5(1)

Steve Madden - Hatton. Color Dark Grey. $170.00. 4.0 out of 5 stars

Gray Steve Madden Hatton

Gray Steve Madden Hatton

Brand Name: Steve Madden
Product Name: Hatton
Gender: Men's
Color: Dark Grey
Price: $170
Rating: 4Rated 4 stars out of 5(1)

KEEN - Revel IV Chelsea. Color Black/Black. $179.95. 3.9 out of 5 stars

Black KEEN Revel IV Chelsea

Black KEEN Revel IV Chelsea

+2

Brand Name: KEEN
Product Name: Revel IV Chelsea
Gender: Men's
Color: Black/Black
Price: $179.95
Rating: 4Rated 4 stars out of 5(76)

Ariat - Hybrid Low Western Boots. Color Stone. $159.95. 4.4 out of 5 stars

Navy Ariat Hybrid Low Western Boots

Navy Ariat Hybrid Low Western Boots

Brand Name: Ariat
Product Name: Hybrid Low Western Boots
Gender: Men's
Color: Stone
Price: $159.95
Rating: 4Rated 4 stars out of 5(152)

Deer Stags - Rockland. Color Black/Black. On sale for $75.00. MSRP $90.00. 17% off. 3.7 out of 5 stars

Black Deer Stags Rockland

Black Deer Stags Rockland

+1

Brand Name: Deer Stags
Product Name: Rockland
Gender: Men's
Color: Black/Black
Price: $75MSRP: $9017% OFF
Rating: 4Rated 4 stars out of 5(32)

Steve Madden - Montreaux. Color Black. Low Stock. $130.00.

Low Stock

Black Steve Madden Montreaux

Black Steve Madden Montreaux

Brand Name: Steve Madden
Product Name: Montreaux
Gender: Men's
Color: Black
Price: $130
Rating

Stacy Adams - Thompson Elastic Lace Inside Zip Boots. Color Black. On sale for $120.00. MSRP $150.00. 20% off.

Black Stacy Adams Thompson Elastic Lace Inside Zip Boots

Black Stacy Adams Thompson Elastic Lace Inside Zip Boots

+2

Brand Name: Stacy Adams
Product Name: Thompson Elastic Lace Inside Zip Boots
Gender: Men's
Color: Black
Price: $120MSRP: $15020% OFF
Rating

Florsheim - Loedin Boot. Color Black. On sale for $134.95. MSRP $162.00. 17% off. 4.5 out of 5 stars

Black Florsheim Loedin Boot

Black Florsheim Loedin Boot

Brand Name: Florsheim
Product Name: Loedin Boot
Gender: Men's
Color: Black
Price: $134.95MSRP: $16217% OFF
Rating: 4Rated 4 stars out of 5(105)

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(360)

Ariat - Groundbreaker Chelsea H2O Steel Toe. Color Dark Brown. $179.95. 4.2 out of 5 stars

Brown Ariat Groundbreaker Chelsea H2O Steel Toe

Brown Ariat Groundbreaker Chelsea H2O Steel Toe

Brand Name: Ariat
Product Name: Groundbreaker Chelsea H2O Steel Toe
Gender: Men's
Color: Dark Brown
Price: $179.95
Rating: 4Rated 4 stars out of 5(141)

Johnston & Murphy - XC Flex Raleigh Chelsea. Color Tan Full Grain. Low Stock. $185.00. 4.4 out of 5 stars

Low Stock

Tan Johnston & Murphy XC Flex Raleigh Chelsea

Tan Johnston & Murphy XC Flex Raleigh Chelsea

Brand Name: Johnston & Murphy
Product Name: XC Flex Raleigh Chelsea
Gender: Men's
Color: Tan Full Grain
Price: $185
Rating: 4Rated 4 stars out of 5(69)

. Timberland PRO - Nashoba Composite Safety Toe. Color Black-2024 NEW. On sale for $160.96. MSRP $180.00. 11% off. 3.8 out of 5 stars

Black Timberland PRO Nashoba Composite Safety Toe

Black Timberland PRO Nashoba Composite Safety Toe

+2

Brand Name: Timberland PRO
Product Name: Nashoba Composite Safety Toe
Gender: Unisex
Color: Black-2024 NEW
Price: $160.96MSRP: $18011% OFF
Rating: 4Rated 4 stars out of 5(86)

Caterpillar - Threshold Rebound Chelsea WP ST. Color Bison. $144.95.

Brown Caterpillar Threshold Rebound Chelsea WP ST

Brown Caterpillar Threshold Rebound Chelsea WP ST

Brand Name: Caterpillar
Product Name: Threshold Rebound Chelsea WP ST
Gender: Men's
Color: Bison
Price: $144.95
Rating

Tommy Hilfiger - Vitus. Color Black. On sale for $59.50. MSRP $119.00. 50% off. 4.0 out of 5 stars

Black Tommy Hilfiger Vitus

Black Tommy Hilfiger Vitus

Brand Name: Tommy Hilfiger
Product Name: Vitus
Gender: Men's
Color: Black
Price: $59.50MSRP: $11950% OFF
Rating: 4Rated 4 stars out of 5(1)

Carhartt - Frontier 6" Water Resistant Boots. Color Mossy Brown. Low Stock. $129.99. 4.2 out of 5 stars

Low Stock

Brown Carhartt Frontier 6" Water Resistant Boots

Brown Carhartt Frontier 6" Water Resistant Boots

Brand Name: Carhartt
Product Name: Frontier 6" Water Resistant Boots
Gender: Men's
Color: Mossy Brown
Price: $129.99
Rating: 4Rated 4 stars out of 5(17)

L.L.Bean - Stonington Chelsea Boot Suede. Color Deepest Brown. On sale for $124.00. MSRP $139.00. 11% off. 3.8 out of 5 stars

Brown L.L.Bean Stonington Chelsea Boot Suede

Brown L.L.Bean Stonington Chelsea Boot Suede

Brand Name: L.L.Bean
Product Name: Stonington Chelsea Boot Suede
Gender: Men's
Color: Deepest Brown
Price: $124MSRP: $13911% OFF
Rating: 4Rated 4 stars out of 5(6)

Caterpillar - Wheelbase Steel Toe. Color Clay Leather. $114.95. 3.0 out of 5 stars

Orange Caterpillar Wheelbase Steel Toe

Orange Caterpillar Wheelbase Steel Toe

Brand Name: Caterpillar
Product Name: Wheelbase Steel Toe
Gender: Men's
Color: Clay Leather
Price: $114.95
Rating: 3Rated 3 stars out of 5(1)

Eastland 1955 Edition - Daily Double. Color Brown Nubuck. Low Stock. On sale for $100.00. MSRP $125.00. 20% off. 3.4 out of 5 stars

Low Stock

Brown Eastland 1955 Edition Daily Double

Brown Eastland 1955 Edition Daily Double

+2

Brand Name: Eastland 1955 Edition
Product Name: Daily Double
Gender: Men's
Color: Brown Nubuck
Price: $100MSRP: $12520% OFF
Rating: 3Rated 3 stars out of 5(14)

Cole Haan - American Classics Chelsea Boots. Color Morel Nubuck Waterproof/Black. On sale for $176.20. MSRP $200.00. 12% off.

Taupe Cole Haan American Classics Chelsea Boots

Taupe Cole Haan American Classics Chelsea Boots

+2

Brand Name: Cole Haan
Product Name: American Classics Chelsea Boots
Gender: Men's
Color: Morel Nubuck Waterproof/Black
Price: $176.20MSRP: $20012% OFF
Rating

SOREL - Cyprus Chelsea Waterproof. Color Khaki Ii/Jet. On sale for $93.75. MSRP $125.00. 25% off. 1.0 out of 5 stars

Khaki SOREL Cyprus Chelsea Waterproof

Khaki SOREL Cyprus Chelsea Waterproof

+3

Brand Name: SOREL
Product Name: Cyprus Chelsea Waterproof
Gender: Men's
Color: Khaki Ii/Jet
Price: $93.75MSRP: $12525% OFF
Rating: 1Rated 1 star out of 5(1)

Stacy Adams - Eastmont Elastic Lace Boots. Color White. Low Stock. On sale for $77.00. MSRP $140.00. 45% off. 4.0 out of 5 stars

Low Stock

White Stacy Adams Eastmont Elastic Lace Boots

White Stacy Adams Eastmont Elastic Lace Boots

+2

Brand Name: Stacy Adams
Product Name: Eastmont Elastic Lace Boots
Gender: Men's
Color: White
Price: $77MSRP: $14045% OFF
Rating: 4Rated 4 stars out of 5(1)

Clarks - Shepton Easy. Color Beeswax Leather. On sale for $116.00. MSRP $130.00. 11% 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: $116MSRP: $13011% OFF
Rating: 5Rated 5 stars out of 5(1)

Vans - Mte™ Standard Mid Chelsea Waterproof. Color 30th Anniversary Gray Olive. On sale for $90.00. MSRP $150.00. 40% off. 3.2 out of 5 stars

White Vans Mte™ Standard Mid Chelsea Waterproof

White Vans Mte™ Standard Mid Chelsea Waterproof

+3

Brand Name: Vans
Product Name: Mte™ Standard Mid Chelsea Waterproof
Gender: Unisex
Color: 30th Anniversary Gray Olive
Price: $90MSRP: $15040% OFF
Rating: 3Rated 3 stars out of 5(4)

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(28)

Johnston & Murphy - Calder Chelsea Boots. Color Brown Oiled Full Grain. $178.95. 5.0 out of 5 stars

Brown Johnston & Murphy Calder Chelsea Boots

Brown Johnston & Murphy Calder Chelsea Boots

Brand Name: Johnston & Murphy
Product Name: Calder Chelsea Boots
Gender: Men's
Color: Brown Oiled Full Grain
Price: $178.95
Rating: 5Rated 5 stars out of 5(1)

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)

Deer Stags - Brayden. Color Black. On sale for $70.00. MSRP $100.00. 30% off. 3.3 out of 5 stars

Black Deer Stags Brayden

Black Deer Stags Brayden

Brand Name: Deer Stags
Product Name: Brayden
Gender: Men's
Color: Black
Price: $70MSRP: $10030% OFF
Rating: 3Rated 3 stars out of 5(3)

Tommy Hilfiger - Berton. Color Cognac. On sale for $89.25. MSRP $119.00. 25% off.

Tan Tommy Hilfiger Berton

Tan Tommy Hilfiger Berton

+2

Brand Name: Tommy Hilfiger
Product Name: Berton
Gender: Men's
Color: Cognac
Price: $89.25MSRP: $11925% OFF
Rating

Marc Joseph New York - Austin. Color Cognac Grainy. On sale for $89.95. MSRP $195.00. 54% off. 4.1 out of 5 stars

Brown Marc Joseph New York Austin

Brown Marc Joseph New York Austin

Brand Name: Marc Joseph New York
Product Name: Austin
Gender: Men's
Color: Cognac Grainy
Price: $89.95MSRP: $19554% OFF
Rating: 4Rated 4 stars out of 5(9)

KEEN - KNX Chukka. Color Brindle/Plaza Taupe. Low Stock. On sale for $91.91. MSRP $159.95. 43% off. 3.8 out of 5 stars

Low Stock

Taupe KEEN KNX Chukka

Taupe KEEN KNX Chukka

Brand Name: KEEN
Product Name: KNX Chukka
Gender: Men's
Color: Brindle/Plaza Taupe
Price: $91.91MSRP: $159.9543% OFF
Rating: 4Rated 4 stars out of 5(20)

Steve Madden - Duke. Color Cognac Leather. $140.00. 5.0 out of 5 stars

Brown Steve Madden Duke

Brown Steve Madden Duke

+2

Brand Name: Steve Madden
Product Name: Duke
Gender: Men's
Color: Cognac Leather
Price: $140
Rating: 5Rated 5 stars out of 5(1)

Twisted X - 4" Work Chelsea Boot. Color Black. Low Stock. $184.95.

Low Stock

Black Twisted X 4" Work Chelsea Boot

Black Twisted X 4" Work Chelsea Boot

+2

Brand Name: Twisted X
Product Name: 4" Work Chelsea Boot
Gender: Men's
Color: Black
Price: $184.95
Rating

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