EXTRA 20% OFF*
*Offer ends 12/29/25 at 11:59pm PST. Exclusions apply.
Hurry, hurry: use code SAVE20
Select styles only.
Shop Now

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

Size 7.5 Ankle Elastic Products

52 items found

Filters

Search Results

. 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(18)

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)

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(8)

Vans - Mte™ Standard Mid Chelsea Waterproof. Color Faded Black. Low Stock. On sale for $112.50. MSRP $150.00. 25% off. 2.0 out of 5 stars

Low Stock

Gray Vans Mte™ Standard Mid Chelsea Waterproof

Gray Vans Mte™ Standard Mid Chelsea Waterproof

+4

Brand Name: Vans
Product Name: Mte™ Standard Mid Chelsea Waterproof
Gender: Unisex
Color: Faded Black
Price: $112.50MSRP: $15025% OFF
Rating: 2Rated 2 stars out of 5(1)

Florsheim - Lodge Plain Toe Gore Boots. Color Chestnut Smooth. On sale for $99.97. MSRP $145.00. 31% off. 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: $99.97MSRP: $14531% OFF
Rating: 4Rated 4 stars out of 5(116)

SOREL - Cyprus Chelsea Waterproof. Color Tobacco/Blackened Brown. Low Stock. $125.00.

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: $125
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)

Stacy Adams - Eastmont Elastic Lace Boots. Color White. On sale for $56.00. MSRP $140.00. 60% off.

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: $56MSRP: $14060% OFF
Rating

Cole Haan - Roundhill Grand Chukka Boots. Color Morel Suede/Dark Natural/Water Resistant. $259.95.

Taupe Cole Haan Roundhill Grand Chukka Boots

Taupe Cole Haan Roundhill Grand Chukka Boots

+3

Brand Name: Cole Haan
Product Name: Roundhill Grand Chukka Boots
Gender: Men's
Color: Morel Suede/Dark Natural/Water Resistant
Price: $259.95
Rating

Clarks - Shepton Easy. Color Black Leather. Low Stock. On sale for $55.90. MSRP $130.00. 57% off. 5.0 out of 5 stars

Low Stock

Black Clarks Shepton Easy

Black Clarks Shepton Easy

+2

Brand Name: Clarks
Product Name: Shepton Easy
Gender: Men's
Color: Black Leather
Price: $55.90MSRP: $13057% OFF
Rating: 5Rated 5 stars out of 5(1)

Florsheim - Forge Plain Toe Gore Boots. Color Brown Crazy Horse. $130.00. 4.1 out of 5 stars

Brown Florsheim Forge Plain Toe Gore Boots

Brown Florsheim Forge Plain Toe Gore Boots

+3

Brand Name: Florsheim
Product Name: Forge Plain Toe Gore Boots
Gender: Men's
Color: Brown Crazy Horse
Price: $130
Rating: 4Rated 4 stars out of 5(19)

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)

Steve Madden - Hatford. Color Black. On sale for $87.20. MSRP $100.00. 13% off.

Black Steve Madden Hatford

Black Steve Madden Hatford

+4

Brand Name: Steve Madden
Product Name: Hatford
Gender: Men's
Color: Black
Price: $87.20MSRP: $10013% OFF
Rating

BRUNT - The Ohman Comp Toe. Color Brown. $149.99. 3.7 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(15)

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(2)

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 Tan. On sale for $67.99. MSRP $79.99. 15% off.

Tan Steve Madden Merrnie

Tan Steve Madden Merrnie

+2

Brand Name: Steve Madden
Product Name: Merrnie
Gender: Men's
Color: Tan
Price: $67.99MSRP: $79.9915% OFF
Rating

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

Low Stock

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)

Cole Haan - Roundhill Grand Chelsea Boots. Color Black/Black Waterproof. On sale for $234.00. MSRP $260.00. 10% off. 5.0 out of 5 stars

Black Cole Haan Roundhill Grand Chelsea Boots

Black Cole Haan Roundhill Grand Chelsea Boots

+2

Brand Name: Cole Haan
Product Name: Roundhill Grand Chelsea Boots
Gender: Men's
Color: Black/Black Waterproof
Price: $234MSRP: $26010% OFF
Rating: 5Rated 5 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. 4.5 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(147)

Timberland PRO - Nashoba Soft Toe. Color Stout Brown-2024 NEW. $170.00. 4.2 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(32)

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 - 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(355)

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)

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

Allen Edmonds - Tanner. Color Bitter Chocolate. $550.00.

Brown Allen Edmonds Tanner

Brown Allen Edmonds Tanner

+3

Brand Name: Allen Edmonds
Product Name: Tanner
Gender: Men's
Color: Bitter Chocolate
Price: $550
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)

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)

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)

Timberland PRO - Nashoba Composite Safety Toe. Color Turkish Coffee-2024 NEW. On sale for $164.95. MSRP $180.00. 8% off. 3.8 out of 5 stars

Brown Timberland PRO Nashoba Composite Safety Toe

Brown Timberland PRO Nashoba Composite Safety Toe

+2

Brand Name: Timberland PRO
Product Name: Nashoba Composite Safety Toe
Gender: Unisex
Color: Turkish Coffee-2024 NEW
Price: $164.95MSRP: $1808% OFF
Rating: 4Rated 4 stars out of 5(78)

Carhartt - Millbrook 4" Romeo Steel Toe Wedge Work Boots. Color Brown Oil Tanned. $149.99. 4.1 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(8)

Avenger Work Boots - Foreman Chelsea CT. Color Brown. On sale for $104.99. MSRP $114.99. 9% off. 3.7 out of 5 stars

Brown Avenger Work Boots Foreman Chelsea CT

Brown Avenger Work Boots Foreman Chelsea CT

Brand Name: Avenger Work Boots
Product Name: Foreman Chelsea CT
Gender: Men's
Color: Brown
Price: $104.99MSRP: $114.999% OFF
Rating: 4Rated 4 stars out of 5(62)

Carhartt - Frontier 6" Water Resistant Boots. Color Mossy Brown. $129.99. 4.1 out of 5 stars

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(10)

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(301)

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

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

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

L.L.Bean - Stonington Chelsea Boot Suede. Color Deepest Brown. $139.00. 3.6 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: $139
Rating: 4Rated 4 stars out of 5(5)

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)

Carhartt - Force Wr 4" Romeo Soft Toe Boot. Color Black Oil Tanned. Low Stock. $139.99. 3.0 out of 5 stars

Low Stock

Black Carhartt Force Wr 4" Romeo Soft Toe Boot

Black Carhartt Force Wr 4" Romeo Soft Toe Boot

Brand Name: Carhartt
Product Name: Force Wr 4" Romeo Soft Toe Boot
Gender: Men's
Color: Black Oil Tanned
Price: $139.99
Rating: 3Rated 3 stars out of 5(5)

Allen Edmonds - Liverpool. Color Black Custom Calf. $550.00. 4.3 out of 5 stars

Black Allen Edmonds Liverpool

Black Allen Edmonds Liverpool

+4

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

Dansko - Frankie. Color Honey Distressed. $179.95. 4.2 out of 5 stars

Brown Dansko Frankie

Brown Dansko Frankie

+3

Brand Name: Dansko
Product Name: Frankie
Gender: Women's
Color: Honey Distressed
Price: $179.95
Rating: 4Rated 4 stars out of 5(305)

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

Brown Steve Madden Highline

Brown Steve Madden Highline

+3

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)

Red Wing Heritage - Classic Chelsea. Color Black Harness. On sale for $298.95. MSRP $329.99. 9% off. 4.3 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: 4Rated 4 stars out of 5(15)

Cole Haan - American Classics Chelsea Boots. Color Madeira Waterproof/Dark Java/Dark Java. On sale for $193.34. MSRP $200.00. 3% off.

Mahogany Cole Haan American Classics Chelsea Boots

Mahogany Cole Haan American Classics Chelsea Boots

+2

Brand Name: Cole Haan
Product Name: American Classics Chelsea Boots
Gender: Men's
Color: Madeira Waterproof/Dark Java/Dark Java
Price: $193.34MSRP: $2003% OFF
Rating

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(248)

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)

Steve Madden - Hatton. Color Black. On sale for $132.00. MSRP $165.00. 20% off. 4.0 out of 5 stars

Black Steve Madden Hatton

Black Steve Madden Hatton

Brand Name: Steve Madden
Product Name: Hatton
Gender: Men's
Color: Black
Price: $132MSRP: $16520% OFF
Rating: 4Rated 4 stars out of 5(1)

To Boot New York - Largo. Color Brown. $494.95. 5.0 out of 5 stars

Brown To Boot New York Largo

Brown To Boot New York Largo

Brand Name: To Boot New York
Product Name: Largo
Gender: Men's
Color: Brown
Price: $494.95
Rating: 5Rated 5 stars out of 5(3)

. Carhartt - Millbrook 4" Romeo Soft Toe Wedge Boots. Color Black Oil Tanned. On sale for $110.00. MSRP $144.99. 24% off. 3.6 out of 5 stars

Black Carhartt Millbrook 4" Romeo Soft Toe Wedge Boots

Black Carhartt Millbrook 4" Romeo Soft Toe Wedge Boots

+2

Brand Name: Carhartt
Product Name: Millbrook 4" Romeo Soft Toe Wedge Boots
Gender: Men's
Color: Black Oil Tanned
Price: $110MSRP: $144.9924% OFF
Rating: 4Rated 4 stars out of 5(49)

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)

Nunn Bush - Otis Plain Toe Chelsea Boot with KORE Walking Comfort Technology. Color Brown CH. On sale for $98.20. MSRP $115.00. 15% off. 4.2 out of 5 stars

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

Brown 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: Brown CH
Price: $98.20MSRP: $11515% OFF
Rating: 4Rated 4 stars out of 5(102)

Join Our Email List

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

*One code per email address.