NEW TO SALE
Get in on the savings while they last.
Shop Now

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

Medium Size Ankle Elastic Shoes

124 items found

Filters

Search Results

. Blundstone - BL587. Color Rustic Black. $209.95. 4.4 out of 5 stars

Black Blundstone BL587

Black Blundstone BL587

Brand Name: Blundstone
Product Name: BL587
Gender: Unisex
Color: Rustic Black
Price: $209.95
Rating: 4Rated 4 stars out of 5(28)

Bogs - Classic II Mid. Color Dark Green. $140.00. 4.0 out of 5 stars

Green Bogs Classic II Mid

Green Bogs Classic II Mid

+3

Brand Name: Bogs
Product Name: Classic II Mid
Gender: Men's
Color: Dark Green
Price: $140
Rating: 4Rated 4 stars out of 5(1)

. Blundstone - BL558. Color Black. $209.95. 4.2 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(21)

Blundstone - BL566. Color Black. $239.95. 5.0 out of 5 stars

Black Blundstone BL566

Black Blundstone BL566

Brand Name: Blundstone
Product Name: BL566
Gender: Unisex
Color: Black
Price: $239.95
Rating: 5Rated 5 stars out of 5(3)

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)

Dr. Martens - Embury. Color Gunmetal. $130.00. 4.1 out of 5 stars

Gray Dr. Martens Embury

Gray Dr. Martens Embury

+3

Brand Name: Dr. Martens
Product Name: Embury
Gender: Unisex
Color: Gunmetal
Price: $130
Rating: 4Rated 4 stars out of 5(116)

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(124)

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. 4.2 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(305)

UGG - Ultra Mini Crafted Regenerate. Color Sand. On sale for $114.93. MSRP $200.00. 43% off. 4.0 out of 5 stars

Bone UGG Ultra Mini Crafted Regenerate

Bone UGG Ultra Mini Crafted Regenerate

Brand Name: UGG
Product Name: Ultra Mini Crafted Regenerate
Gender: Unisex
Color: Sand
Price: $114.93MSRP: $20043% OFF
Rating: 4Rated 4 stars out of 5(60)

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(9)

Dr. Martens - 2976 Leather Chelsea Boots. Color Cashew. On sale for $135.95. MSRP $180.00. 24% off. 3.5 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: $135.95MSRP: $18024% OFF
Rating: 4Rated 4 stars out of 5(13)

Johnston & Murphy - Upton Chelsea. Color Brown Oiled Full Grain. Low Stock. On sale for $119.99. MSRP $179.00. 33% off. 4.4 out of 5 stars

Low Stock

Brown Johnston & Murphy Upton Chelsea

Brown Johnston & Murphy Upton Chelsea

Brand Name: Johnston & Murphy
Product Name: Upton Chelsea
Gender: Men's
Color: Brown Oiled Full Grain
Price: $119.99MSRP: $17933% OFF
Rating: 4Rated 4 stars out of 5(203)

Bogs - Digger Slip-On. Color Olive. $85.00. 3.9 out of 5 stars

Olive Bogs Digger Slip-On

Olive Bogs Digger Slip-On

+2

Brand Name: Bogs
Product Name: Digger Slip-On
Gender: Men's
Color: Olive
Price: $85
Rating: 4Rated 4 stars out of 5(110)

Stacy Adams - Eastmont Elastic Lace Boots. Color White. Low Stock. On sale for $126.00. MSRP $140.00. 10% off. 4.0 out of 5 stars

Low Stock

White Stacy Adams Eastmont Elastic Lace Boots

White Stacy Adams Eastmont Elastic Lace Boots

+3

Brand Name: Stacy Adams
Product Name: Eastmont Elastic Lace Boots
Gender: Men's
Color: White
Price: $126MSRP: $14010% OFF
Rating: 4Rated 4 stars out of 5(1)

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)

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

Black Ariat Wexford Waterproof

Black Ariat Wexford Waterproof

+2

Brand Name: Ariat
Product Name: Wexford Waterproof
Gender: Men's
Color: Black
Price: $209.95
Rating: 4Rated 4 stars out of 5(251)

Steve Madden - Highline. Color Chocolate Brown 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: Chocolate Brown Suede
Price: $109.95
Rating: 4Rated 4 stars out of 5(22)

L.L.Bean - Bean Boot 6.5" Chelsea. Color Deep Blue/Black/Toasted Coconut. Low Stock. $160.00. 3.2 out of 5 stars

Low Stock

Black L.L.Bean Bean Boot 6.5" Chelsea

Black L.L.Bean Bean Boot 6.5" Chelsea

+1

Brand Name: L.L.Bean
Product Name: Bean Boot 6.5" Chelsea
Gender: Men's
Color: Deep Blue/Black/Toasted Coconut
Price: $160
Rating: 3Rated 3 stars out of 5(138)

Dr. Martens - 2976 Yellow Stitch Smooth Leather Chelsea Boots. Color Black Smooth. On sale for $169.95. MSRP $180.00. 6% off. 3.8 out of 5 stars

Black Dr. Martens 2976 Yellow Stitch Smooth Leather Chelsea Boots

Black 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: Black Smooth
Price: $169.95MSRP: $1806% OFF
Rating: 4Rated 4 stars out of 5(42)

Frye - Tyler Flex Chelsea. Color Bark. Low Stock. On sale for $241.20. MSRP $268.00. 10% off. 3.6 out of 5 stars

Low Stock

Brown Frye Tyler Flex Chelsea

Brown Frye Tyler Flex Chelsea

+4

Brand Name: Frye
Product Name: Tyler Flex Chelsea
Gender: Men's
Color: Bark
Price: $241.20MSRP: $26810% OFF
Rating: 4Rated 4 stars out of 5(8)

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)

Cole Haan - American Classics Chelsea Boots. Color Black Waterproof/Black/Black. Low Stock. On sale for $170.00. MSRP $200.00. 15% off.

Low Stock

Black Cole Haan American Classics Chelsea Boots

Black Cole Haan American Classics Chelsea Boots

+3

Brand Name: Cole Haan
Product Name: American Classics Chelsea Boots
Gender: Men's
Color: Black Waterproof/Black/Black
Price: $170MSRP: $20015% OFF
Rating

Hunter - Original Chelsea. Color Dark Olive 1. $175.00. 4.2 out of 5 stars

Olive Hunter Original Chelsea

Olive Hunter Original Chelsea

+3

Brand Name: Hunter
Product Name: Original Chelsea
Gender: Men's
Color: Dark Olive 1
Price: $175
Rating: 4Rated 4 stars out of 5(21)

Tommy Hilfiger - Sesame. Color Medium Brown Burnished. On sale for $71.40. MSRP $119.00. 40% 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: $71.40MSRP: $11940% OFF
Rating: 5Rated 5 stars out of 5(6)

Sperry - Clifton Boots. Color Olive. On sale for $104.99. MSRP $110.00. 5% off. 5.0 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: 5Rated 5 stars out of 5(1)

Clarks - Shepton Easy. Color Black Leather. On sale for $108.75. MSRP $130.00. 16% off. 5.0 out of 5 stars

Black Clarks Shepton Easy

Black Clarks Shepton Easy

+2

Brand Name: Clarks
Product Name: Shepton Easy
Gender: Men's
Color: Black Leather
Price: $108.75MSRP: $13016% OFF
Rating: 5Rated 5 stars out of 5(1)

Bogs - Arcata Urban Chelsea. Color Black. On sale for $115.46. MSRP $165.00. 30% off. 3.9 out of 5 stars

Black Bogs Arcata Urban Chelsea

Black Bogs Arcata Urban Chelsea

Brand Name: Bogs
Product Name: Arcata Urban Chelsea
Gender: Men's
Color: Black
Price: $115.46MSRP: $16530% OFF
Rating: 4Rated 4 stars out of 5(93)

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)

Dr. Martens - 2976 Platform Faux-Fur Lined. Color Black. $219.95. 4.1 out of 5 stars

Black Dr. Martens 2976 Platform Faux-Fur Lined

Black Dr. Martens 2976 Platform Faux-Fur Lined

Brand Name: Dr. Martens
Product Name: 2976 Platform Faux-Fur Lined
Gender: Unisex
Color: Black
Price: $219.95
Rating: 4Rated 4 stars out of 5(15)

Johnston & Murphy - Calder Chelsea Boots. Color Mahogany Full Grain. $178.95.

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: Mahogany Full Grain
Price: $178.95
Rating

Dr. Martens - 2976 Quad Smooth Leather Platform Chelsea Boots. Color Black Polished Smooth. On sale for $189.00. MSRP $210.00. 10% off. 4.2 out of 5 stars

Black Dr. Martens 2976 Quad Smooth Leather Platform Chelsea Boots

Black Dr. Martens 2976 Quad Smooth Leather Platform Chelsea Boots

Brand Name: Dr. Martens
Product Name: 2976 Quad Smooth Leather Platform Chelsea Boots
Gender: Unisex
Color: Black Polished Smooth
Price: $189MSRP: $21010% OFF
Rating: 4Rated 4 stars out of 5(34)

Florsheim - Forge Plain Toe Gore Boots. Color Cognac. $130.00. 4.0 out of 5 stars

Tan Florsheim Forge Plain Toe Gore Boots

Tan Florsheim Forge Plain Toe Gore Boots

+3

Brand Name: Florsheim
Product Name: Forge Plain Toe Gore Boots
Gender: Men's
Color: Cognac
Price: $130
Rating: 4Rated 4 stars out of 5(26)

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

Cole Haan - Roundhill Grand Chukka Boots. Color Black Nubuck/Water Resistant. Low Stock. $259.95.

Low Stock

Black Cole Haan Roundhill Grand Chukka Boots

Black Cole Haan Roundhill Grand Chukka Boots

+3

Brand Name: Cole Haan
Product Name: Roundhill Grand Chukka Boots
Gender: Men's
Color: Black Nubuck/Water Resistant
Price: $259.95
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)

L.L.Bean - Storm Chaser Chelsea Boots. Color Oakwood. $170.00. 3.5 out of 5 stars

Brown L.L.Bean Storm Chaser Chelsea Boots

Brown L.L.Bean Storm Chaser Chelsea Boots

+2

Brand Name: L.L.Bean
Product Name: Storm Chaser Chelsea Boots
Gender: Men's
Color: Oakwood
Price: $170
Rating: 3Rated 3 stars out of 5(35)

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

Blundstone - BL490 Work Chelsea Boot. Color Stout Brown. $214.95. 4.5 out of 5 stars

Brown Blundstone BL490 Work Chelsea Boot

Brown Blundstone BL490 Work Chelsea Boot

Brand Name: Blundstone
Product Name: BL490 Work Chelsea Boot
Gender: Unisex
Color: Stout Brown
Price: $214.95
Rating: 5Rated 5 stars out of 5(71)

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)

UGG - Neumel Weather Hybrid. Color Obsidian/Cobble Grey. Low Stock. $189.95. 4.3 out of 5 stars

Low Stock

Navy UGG Neumel Weather Hybrid

Navy UGG Neumel Weather Hybrid

+4

Brand Name: UGG
Product Name: Neumel Weather Hybrid
Gender: Men's
Color: Obsidian/Cobble Grey
Price: $189.95
Rating: 4Rated 4 stars out of 5(130)

Johnston & Murphy - XC+ Durham Chelsea Boots. Color Snuff Waterproof Waxed Suede. On sale for $198.95. MSRP $219.00. 9% off.

Brown Johnston & Murphy XC+ Durham Chelsea Boots

Brown Johnston & Murphy XC+ Durham Chelsea Boots

+2

Brand Name: Johnston & Murphy
Product Name: XC+ Durham Chelsea Boots
Gender: Men's
Color: Snuff Waterproof Waxed Suede
Price: $198.95MSRP: $2199% OFF
Rating

Steve Madden - Hatford. Color Black. On sale for $81.93. MSRP $100.00. 18% off.

Black Steve Madden Hatford

Black Steve Madden Hatford

+4

Brand Name: Steve Madden
Product Name: Hatford
Gender: Men's
Color: Black
Price: $81.93MSRP: $10018% OFF
Rating

SOREL - Cyprus Chelsea Waterproof. Color Tobacco/Blackened Brown. Low Stock. On sale for $93.75. MSRP $125.00. 25% off. 1.0 out of 5 stars

Low Stock

Brown SOREL Cyprus Chelsea Waterproof

Brown SOREL Cyprus Chelsea Waterproof

+3

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

Hey Dude - Bradley Chukka. Color Tan. Low Stock. $84.99.

Low Stock

Tan Hey Dude Bradley Chukka

Tan Hey Dude Bradley Chukka

+4

Brand Name: Hey Dude
Product Name: Bradley Chukka
Gender: Men's
Color: Tan
Price: $84.99
Rating

Red Wing Heritage - Classic Chelsea. Color Hawthorne Muleskinner. Low Stock. $299.99. 4.1 out of 5 stars

Low Stock

Khaki Red Wing Heritage Classic Chelsea

Khaki Red Wing Heritage Classic Chelsea

+3

Brand Name: Red Wing Heritage
Product Name: Classic Chelsea
Gender: Men's
Color: Hawthorne Muleskinner
Price: $299.99
Rating: 4Rated 4 stars out of 5(16)

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

Olive KEEN Revel IV Chelsea

Olive KEEN Revel IV Chelsea

+2

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

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)

L.L.Bean - Portland Chelsea Boot. Color Dark Russet. $190.00. 4.1 out of 5 stars

Red L.L.Bean Portland Chelsea Boot

Red L.L.Bean Portland Chelsea Boot

+2

Brand Name: L.L.Bean
Product Name: Portland Chelsea Boot
Gender: Men's
Color: Dark Russet
Price: $190
Rating: 4Rated 4 stars out of 5(24)

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(150)

Dr. Martens - 2976 Bex Smooth Leather Chelsea Boots. Color Black Smooth. On sale for $179.95. MSRP $190.00. 5% off. 3.6 out of 5 stars

Black Dr. Martens 2976 Bex Smooth Leather Chelsea Boots

Black Dr. Martens 2976 Bex Smooth Leather Chelsea Boots

Brand Name: Dr. Martens
Product Name: 2976 Bex Smooth Leather Chelsea Boots
Gender: Unisex
Color: Black Smooth
Price: $179.95MSRP: $1905% OFF
Rating: 4Rated 4 stars out of 5(26)

Dr. Martens - 2976 Vegan Chelsea Boot. Color Black Felix Rub Off. On sale for $143.78. MSRP $170.00. 15% off. 3.6 out of 5 stars

Black Dr. Martens 2976 Vegan Chelsea Boot

Black Dr. Martens 2976 Vegan Chelsea Boot

Brand Name: Dr. Martens
Product Name: 2976 Vegan Chelsea Boot
Gender: Unisex
Color: Black Felix Rub Off
Price: $143.78MSRP: $17015% OFF
Rating: 4Rated 4 stars out of 5(36)

BRUNT - The Ohman Comp Toe. Color Brown. $149.99. 3.9 out of 5 stars

Brown BRUNT The Ohman Comp Toe

Brown BRUNT The Ohman Comp Toe

+2

Brand Name: BRUNT
Product Name: The Ohman Comp Toe
Gender: Men's
Color: Brown
Price: $149.99
Rating: 4Rated 4 stars out of 5(18)

Dr. Martens - Hardie II. Color Whiskey Pit Quarter. On sale for $109.95. MSRP $120.00. 8% off. 4.2 out of 5 stars

Brown Dr. Martens Hardie II

Brown Dr. Martens Hardie II

+2

Brand Name: Dr. Martens
Product Name: Hardie II
Gender: Unisex
Color: Whiskey Pit Quarter
Price: $109.95MSRP: $1208% OFF
Rating: 4Rated 4 stars out of 5(24)

. Bogs - Spruce Chelsea. Color Gray. $149.95. 3.7 out of 5 stars

Gray Bogs Spruce Chelsea

Gray Bogs Spruce Chelsea

+2

Brand Name: Bogs
Product Name: Spruce Chelsea
Gender: Men's
Color: Gray
Price: $149.95
Rating: 4Rated 4 stars out of 5(44)

Pajar CANADA - Fortuo 2.0. Color Black/Black. Low Stock. $210.00.

Low Stock

Black Pajar CANADA Fortuo 2.0

Black Pajar CANADA Fortuo 2.0

+3

Brand Name: Pajar CANADA
Product Name: Fortuo 2.0
Gender: Men's
Color: Black/Black
Price: $210
Rating

Dr. Martens - 2976 Chelsea SR Boots. Color Black. On sale for $169.95. MSRP $190.00. 11% off. 4.4 out of 5 stars

Black Dr. Martens 2976 Chelsea SR Boots

Black Dr. Martens 2976 Chelsea SR Boots

Brand Name: Dr. Martens
Product Name: 2976 Chelsea SR Boots
Gender: Unisex
Color: Black
Price: $169.95MSRP: $19011% OFF
Rating: 4Rated 4 stars out of 5(76)

Kenneth Cole - Tully Chelsea Boots. Color Black Leather. On sale for $148.00. MSRP $184.95. 20% off.

Black Kenneth Cole Tully Chelsea Boots

Black Kenneth Cole Tully Chelsea Boots

Brand Name: Kenneth Cole
Product Name: Tully Chelsea Boots
Gender: Men's
Color: Black Leather
Price: $148MSRP: $184.9520% OFF
Rating

Deer Stags - Rockland. Color Redwood/Dark Brown. On sale for $58.50. MSRP $90.00. 35% 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: $58.50MSRP: $9035% OFF
Rating: 4Rated 4 stars out of 5(32)

Stacy Adams - Thompson Elastic Lace Inside Zip Boots. Color Brown. On sale for $135.00. MSRP $150.00. 10% off.

Brown Stacy Adams Thompson Elastic Lace Inside Zip Boots

Brown 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: Brown
Price: $135MSRP: $15010% OFF
Rating

Blundstone - All-Terrain Chelsea Boots. Color Rustic Black. Low Stock. $234.95.

Low Stock

Black Blundstone All-Terrain Chelsea Boots

Black Blundstone All-Terrain Chelsea Boots

Brand Name: Blundstone
Product Name: All-Terrain Chelsea Boots
Gender: Unisex
Color: Rustic Black
Price: $234.95
Rating

Stacy Adams - Isaacson Chelsea Boots. Color Cognac. On sale for $104.99. MSRP $150.00. 30% off. 1.0 out of 5 stars

Tan Stacy Adams Isaacson Chelsea Boots

Tan Stacy Adams Isaacson Chelsea Boots

Brand Name: Stacy Adams
Product Name: Isaacson Chelsea Boots
Gender: Men's
Color: Cognac
Price: $104.99MSRP: $15030% OFF
Rating

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

To Boot New York - Christophe. Color Black. Low Stock. On sale for $420.75. MSRP $495.00. 15% off.

Low Stock

Black To Boot New York Christophe

Black To Boot New York Christophe

+3

Brand Name: To Boot New York
Product Name: Christophe
Gender: Men's
Color: Black
Price: $420.75MSRP: $49515% OFF
Rating

Timberland PRO - Nashoba Soft Toe. Color Stout Brown-2024 NEW. $170.00. 4.3 out of 5 stars

Brown Timberland PRO Nashoba Soft Toe

Brown Timberland PRO Nashoba Soft Toe

Brand Name: Timberland PRO
Product Name: Nashoba Soft Toe
Gender: Unisex
Color: Stout Brown-2024 NEW
Price: $170
Rating: 4Rated 4 stars out of 5(36)

Sanuk - Chel-sea Rain. Color Mushroom. On sale for $80.00. MSRP $100.00. 20% off.

Neutral Sanuk Chel-sea Rain

Neutral Sanuk Chel-sea Rain

Brand Name: Sanuk
Product Name: Chel-sea Rain
Gender: Men's
Color: Mushroom
Price: $80MSRP: $10020% OFF
Rating

Blundstone - BL491 Work Chelsea Boot. Color Black. $214.95. 4.1 out of 5 stars

Black Blundstone BL491 Work Chelsea Boot

Black Blundstone BL491 Work Chelsea Boot

Brand Name: Blundstone
Product Name: BL491 Work Chelsea Boot
Gender: Unisex
Color: Black
Price: $214.95
Rating: 4Rated 4 stars out of 5(11)

Barbour - Tinstone Chelsea Boots. Color Choc Suede. Low Stock. $245.00.

Low Stock

Brown Barbour Tinstone Chelsea Boots

Brown Barbour Tinstone Chelsea Boots

+2

Brand Name: Barbour
Product Name: Tinstone Chelsea Boots
Gender: Men's
Color: Choc Suede
Price: $245
Rating

Cole Haan - Roundhill Grand Chelsea Boots. Color Woodbury/Water Resistant. Low Stock. On sale for $195.00. MSRP $260.00. 25% off. 5.0 out of 5 stars

Low Stock

Brown Cole Haan Roundhill Grand Chelsea Boots

Brown Cole Haan Roundhill Grand Chelsea Boots

+2

Brand Name: Cole Haan
Product Name: Roundhill Grand Chelsea Boots
Gender: Men's
Color: Woodbury/Water Resistant
Price: $195MSRP: $26025% OFF
Rating: 5Rated 5 stars out of 5(1)

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)

Johnston & Murphy - Upton Chelsea Boots. Color Tan Full Grain. On sale for $161.10. MSRP $179.00. 10% 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: $161.10MSRP: $17910% OFF
Rating: 2Rated 2 stars out of 5(1)

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

Navy Ariat Midtown Rambler

Navy Ariat Midtown Rambler

+2 colors/patterns

Brand Name: Ariat
Product Name: Midtown Rambler
Gender: Men's
Color: Stone
Price: $169.95
Rating: 4Rated 4 stars out of 5(356)

Forsake - Phil Chelsea. Color Gray. Low Stock. $145.00. 4.0 out of 5 stars

Low Stock

Gray Forsake Phil Chelsea

Gray Forsake Phil Chelsea

+3

Brand Name: Forsake
Product Name: Phil Chelsea
Gender: Men's
Color: Gray
Price: $145
Rating: 4Rated 4 stars out of 5(47)

Dr. Martens - 2976 Harness. Color Black. On sale for $143.95. MSRP $180.00. 20% off. 3.0 out of 5 stars

Black Dr. Martens 2976 Harness

Black Dr. Martens 2976 Harness

Brand Name: Dr. Martens
Product Name: 2976 Harness
Gender: Unisex
Color: Black
Price: $143.95MSRP: $18020% OFF
Rating: 3Rated 3 stars out of 5(1)

To Boot New York - Largo. Color Black. On sale for $445.50. MSRP $495.00. 10% off. 5.0 out of 5 stars

Black To Boot New York Largo

Black To Boot New York Largo

Brand Name: To Boot New York
Product Name: Largo
Gender: Men's
Color: Black
Price: $445.50MSRP: $49510% OFF
Rating: 5Rated 5 stars out of 5(3)

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(138)

Tommy Hilfiger - Berton. Color Black. Low Stock. On sale for $71.40. MSRP $119.00. 40% off.

Low Stock

Black Tommy Hilfiger Berton

Black Tommy Hilfiger Berton

+2

Brand Name: Tommy Hilfiger
Product Name: Berton
Gender: Men's
Color: Black
Price: $71.40MSRP: $11940% OFF
Rating

. Nisolo - All-Weather Chelsea Boot. Color Dark Tobacco. On sale for $104.00. MSRP $260.00. 60% off. 1.5 out of 5 stars

Red Nisolo All-Weather Chelsea Boot

Red Nisolo All-Weather Chelsea Boot

Brand Name: Nisolo
Product Name: All-Weather Chelsea Boot
Gender: Men's
Color: Dark Tobacco
Price: $104MSRP: $26060% OFF
Rating: 2Rated 2 stars out of 5(2)

Ariat - Midtown Rambler Boots. Color Matte Black. $169.95. 4.4 out of 5 stars

Black Ariat Midtown Rambler Boots

Black Ariat Midtown Rambler Boots

Brand Name: Ariat
Product Name: Midtown Rambler Boots
Gender: Men's
Color: Matte Black
Price: $169.95
Rating: 4Rated 4 stars out of 5(25)

Twisted X - MCA0013. Color Oiled Saddle. $169.95. 5.0 out of 5 stars

Tan Twisted X MCA0013

Tan Twisted X MCA0013

Brand Name: Twisted X
Product Name: MCA0013
Gender: Men's
Color: Oiled Saddle
Price: $169.95
Rating: 5Rated 5 stars out of 5(1)

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)

Stacy Adams - Townsend Chelsea Boots. Color Black Tumble. Low Stock. On sale for $105.00. MSRP $150.00. 30% off.

Low Stock

Black Stacy Adams Townsend Chelsea Boots

Black Stacy Adams Townsend Chelsea Boots

Brand Name: Stacy Adams
Product Name: Townsend Chelsea Boots
Gender: Men's
Color: Black Tumble
Price: $105MSRP: $15030% OFF
Rating

Marc Joseph New York - Austin. Color Truffle Washed Grainy. Low Stock. On sale for $156.00. MSRP $195.00. 20% off. 4.1 out of 5 stars

Low Stock

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: Truffle Washed Grainy
Price: $156MSRP: $19520% OFF
Rating: 4Rated 4 stars out of 5(9)

Bruno Magli - Macy. Color Black. $325.00.

Black Bruno Magli Macy

Black Bruno Magli Macy

Brand Name: Bruno Magli
Product Name: Macy
Gender: Men's
Color: Black
Price: $325
Rating

Ariat - Wexford Waterproof Chelsea Boot. Color Palm Brown. $209.95.

Brown Ariat Wexford Waterproof Chelsea Boot

Brown Ariat Wexford Waterproof Chelsea Boot

Brand Name: Ariat
Product Name: Wexford Waterproof Chelsea Boot
Gender: Men's
Color: Palm Brown
Price: $209.95
Rating

Steve Madden - Duke. Color Black Leather. Low Stock. $140.00. 5.0 out of 5 stars

Low Stock

Black Steve Madden Duke

Black Steve Madden Duke

+2

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

Mephisto - Benson. Color Dark Brown. Low Stock. $449.00. 5.0 out of 5 stars

Low Stock

Brown Mephisto Benson

Brown Mephisto Benson

Brand Name: Mephisto
Product Name: Benson
Gender: Men's
Color: Dark Brown
Price: $449
Rating: 5Rated 5 stars out of 5(4)

Globe - Dover II Trek. Color Wheat/Gum/Summit. On sale for $87.46. MSRP $124.95. 30% off.

Yellow Globe Dover II Trek

Yellow Globe Dover II Trek

Brand Name: Globe
Product Name: Dover II Trek
Gender: Men's
Color: Wheat/Gum/Summit
Price: $87.46MSRP: $124.9530% OFF
Rating

Ariat - Turbo Chelsea Waterproof Carbon Toe EH. Color Aged Bark. $174.95. 4.3 out of 5 stars

Brown Ariat Turbo Chelsea Waterproof Carbon Toe EH

Brown Ariat Turbo Chelsea Waterproof Carbon Toe EH

Brand Name: Ariat
Product Name: Turbo Chelsea Waterproof Carbon Toe EH
Gender: Men's
Color: Aged Bark
Price: $174.95
Rating: 4Rated 4 stars out of 5(304)

. Timberland PRO - Nashoba Composite Safety Toe. Color Black-2024 NEW. On sale for $164.95. MSRP $180.00. 8% 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: $164.95MSRP: $1808% OFF
Rating: 4Rated 4 stars out of 5(82)

Pajar CANADA - Messi. Color Black Nubuck. Low Stock. $275.00.

Low Stock

Black Pajar CANADA Messi

Black Pajar CANADA Messi

Brand Name: Pajar CANADA
Product Name: Messi
Gender: Men's
Color: Black Nubuck
Price: $275
Rating

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

Carhartt - Millbrook 4" Romeo Steel Toe Wedge Work Boots. Color Brown Oil Tanned. $149.99. 4.0 out of 5 stars

Brown Carhartt Millbrook 4" Romeo Steel Toe Wedge Work Boots

Brown Carhartt Millbrook 4" Romeo Steel Toe Wedge Work Boots

Brand Name: Carhartt
Product Name: Millbrook 4" Romeo Steel Toe Wedge Work Boots
Gender: Men's
Color: Brown Oil Tanned
Price: $149.99
Rating: 4Rated 4 stars out of 5(10)

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)

Allen Edmonds - Liverpool. Color Chili. $550.00. 4.3 out of 5 stars

Brown Allen Edmonds Liverpool

Brown Allen Edmonds Liverpool

+4

Brand Name: Allen Edmonds
Product Name: Liverpool
Gender: Men's
Color: Chili
Price: $550
Rating: 4Rated 4 stars out of 5(154)

Nunn Bush - Otis Plain Toe Chelsea Boot with KORE Walking Comfort Technology. Color Black Tumbled. On sale for $103.50. MSRP $115.00. 10% 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

+2

Brand Name: Nunn Bush
Product Name: Otis Plain Toe Chelsea Boot with KORE Walking Comfort Technology
Gender: Men's
Color: Black Tumbled
Price: $103.50MSRP: $11510% OFF
Rating: 4Rated 4 stars out of 5(102)

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(16)

To Boot New York - Lynn. Color Grey Suede. Low Stock. On sale for $212.50. MSRP $425.00. 50% off.

Low Stock

Gray To Boot New York Lynn

Gray To Boot New York Lynn

Brand Name: To Boot New York
Product Name: Lynn
Gender: Men's
Color: Grey Suede
Price: $212.50MSRP: $42550% OFF
Rating

KEEN Utility - Lansing Chelsea Steel Toe. Color Dark Earth/Brindle. On sale for $145.62. MSRP $150.00. 3% off. 3.9 out of 5 stars

Gray KEEN Utility Lansing Chelsea Steel Toe

Gray KEEN Utility Lansing Chelsea Steel Toe

Brand Name: KEEN Utility
Product Name: Lansing Chelsea Steel Toe
Gender: Men's
Color: Dark Earth/Brindle
Price: $145.62MSRP: $1503% OFF
Rating: 4Rated 4 stars out of 5(32)

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)

1 of 2

Join Our Email List

Never miss out on latest drops & sales—plus, new subscribers get 10% off.*

*One code per email address.