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

Medium Size Ankle Chelsea Products

43 items found

Sort By

Your Selections

Search Results

. Blundstone - BL587. Color Rustic Black. $209.95. 4.5 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(25)

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

Brown Blundstone BL2340

Brown Blundstone BL2340

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

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)

BRUNT - The Ohman Soft Toe. Color Black. $139.99. 4.0 out of 5 stars

Black BRUNT The Ohman Soft Toe

Black BRUNT The Ohman Soft Toe

+2

Brand Name: BRUNT
Product Name: The Ohman Soft Toe
Gender: Men's
Color: Black
Price: $139.99
Rating: 4Rated 4 stars out of 5(6)

Blundstone - BL584. Color Rustic Brown. $239.95. 4.1 out of 5 stars

Brown Blundstone BL584

Brown Blundstone BL584

Brand Name: Blundstone
Product Name: BL584
Gender: Unisex
Color: Rustic Brown
Price: $239.95
Rating: 4Rated 4 stars out of 5(8)

Bogs - Sauvie Chelsea II. Color Black. $110.00. 3.9 out of 5 stars

Black Bogs Sauvie Chelsea II

Black Bogs Sauvie Chelsea II

+1

Brand Name: Bogs
Product Name: Sauvie Chelsea II
Gender: Men's
Color: Black
Price: $110
Rating: 4Rated 4 stars out of 5(84)

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)

Blundstone - BL2241. Color Black. $274.95. 4.5 out of 5 stars

Black Blundstone BL2241

Black Blundstone BL2241

Brand Name: Blundstone
Product Name: BL2241
Gender: Unisex
Color: Black
Price: $274.95
Rating: 5Rated 5 stars out of 5(6)

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(20)

Blundstone - BL2242. Color Rustic Brown. $274.95. 4.5 out of 5 stars

Brown Blundstone BL2242

Brown Blundstone BL2242

Brand Name: Blundstone
Product Name: BL2242
Gender: Unisex
Color: Rustic Brown
Price: $274.95
Rating: 5Rated 5 stars out of 5(2)

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)

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)

Blundstone - BL2412. Color Bordeaux Brush. $204.95. 4.5 out of 5 stars

Burgundy Blundstone BL2412

Burgundy Blundstone BL2412

Brand Name: Blundstone
Product Name: BL2412
Gender: Unisex
Color: Bordeaux Brush
Price: $204.95
Rating: 5Rated 5 stars out of 5(2)

Sanuk - Chel-sea Rain. Color Mushroom. On sale for $90.00. MSRP $100.00. 10% 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: $90MSRP: $10010% OFF
Rating

BRUNT - The Ohman BRUNT Toe. Color Brown. $164.99. 5.0 out of 5 stars

Brown BRUNT The Ohman BRUNT Toe

Brown BRUNT The Ohman BRUNT Toe

Brand Name: BRUNT
Product Name: The Ohman BRUNT Toe
Gender: Men's
Color: Brown
Price: $164.99
Rating: 5Rated 5 stars out of 5(3)

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)

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

Low Stock

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)

Cole Haan - Hawthorne Chelsea Boots. Color British Tan. On sale for $153.71. MSRP $168.00. 9% off. 5.0 out of 5 stars

Tan Cole Haan Hawthorne Chelsea Boots

Tan Cole Haan Hawthorne Chelsea Boots

+2

Brand Name: Cole Haan
Product Name: Hawthorne Chelsea Boots
Gender: Men's
Color: British Tan
Price: $153.71MSRP: $1689% OFF
Rating: 5Rated 5 stars out of 5(3)

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

Black Dr. Martens Hardie II

Black Dr. Martens Hardie II

+2

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

Dr. Martens - 2976 Chelsea SR Boots. Color Black. On sale for $169.95. MSRP $180.00. 6% 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: $1806% OFF
Rating: 4Rated 4 stars out of 5(76)

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

Brown Carhartt Frontier Water Resistant Steel Toe Chelsea

Brown Carhartt Frontier Water Resistant Steel Toe Chelsea

Brand Name: Carhartt
Product Name: Frontier Water Resistant Steel Toe Chelsea
Gender: Men's
Color: Brown
Price: $139.99
Rating: 4Rated 4 stars out of 5(10)

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)

Tommy Hilfiger - Berton. Color Cognac. On sale for $83.30. MSRP $119.00. 30% off.

Tan Tommy Hilfiger Berton

Tan Tommy Hilfiger Berton

+2

Brand Name: Tommy Hilfiger
Product Name: Berton
Gender: Men's
Color: Cognac
Price: $83.30MSRP: $11930% OFF
Rating

Florsheim - Loedin Boot. Color Black. On sale for $134.95. MSRP $162.00. 17% off. 4.4 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(101)

Naot - Washington. Color Cordovan Leather. Low Stock. On sale for $174.96. MSRP $249.95. 30% off. 5.0 out of 5 stars

Low Stock

Brown Naot Washington

Brown Naot Washington

+2

Brand Name: Naot
Product Name: Washington
Gender: Men's
Color: Cordovan Leather
Price: $174.96MSRP: $249.9530% OFF
Rating: 5Rated 5 stars out of 5(1)

Eastland 1955 Edition - Chimney Pond. Color Black. On sale for $108.75. MSRP $145.00. 25% off.

Black Eastland 1955 Edition Chimney Pond

Black Eastland 1955 Edition Chimney Pond

Brand Name: Eastland 1955 Edition
Product Name: Chimney Pond
Gender: Men's
Color: Black
Price: $108.75MSRP: $14525% OFF
Rating

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)

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)

. PUMA - Tanami Double Gore EH. Color Brown/Black. On sale for $110.00. MSRP $135.00. 19% off. 3.9 out of 5 stars

Brown PUMA Tanami Double Gore EH

Brown PUMA Tanami Double Gore EH

Brand Name: PUMA
Product Name: Tanami Double Gore EH
Gender: Men's
Color: Brown/Black
Price: $110MSRP: $13519% OFF
Rating: 4Rated 4 stars out of 5(95)

KEEN Utility - Lansing Chelsea Steel Toe. Color Dark Earth/Brindle. $150.00. 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: $150
Rating: 4Rated 4 stars out of 5(32)

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

Timberland PRO - Berkley Chelsea Composite Safety Toe Static Dissipative. Color Black. $155.00. 3.4 out of 5 stars

Black Timberland PRO Berkley Chelsea Composite Safety Toe Static Dissipative

Black Timberland PRO Berkley Chelsea Composite Safety Toe Static Dissipative

Brand Name: Timberland PRO
Product Name: Berkley Chelsea Composite Safety Toe Static Dissipative
Gender: Men's
Color: Black
Price: $155
Rating: 3Rated 3 stars out of 5(13)

Ariat - Rebar Wedge Chelsea Waterproof Work Boots. Color Distressed Brown. $179.95.

Brown Ariat Rebar Wedge Chelsea Waterproof Work Boots

Brown Ariat Rebar Wedge Chelsea Waterproof Work Boots

Brand Name: Ariat
Product Name: Rebar Wedge Chelsea Waterproof Work Boots
Gender: Men's
Color: Distressed Brown
Price: $179.95
Rating

Stacy Adams - Gabriel Chelsea Boot. Color Sand Suede. Low Stock. On sale for $94.95. MSRP $130.00. 27% off. 4.2 out of 5 stars

Low Stock

Tan Stacy Adams Gabriel Chelsea Boot

Tan Stacy Adams Gabriel Chelsea Boot

Brand Name: Stacy Adams
Product Name: Gabriel Chelsea Boot
Gender: Men's
Color: Sand Suede
Price: $94.95MSRP: $13027% OFF
Rating: 4Rated 4 stars out of 5(19)

Ariat - Turbo Chelsea CSA Waterproof Carbon Toe Work Boots. Color Rich Brown. Low Stock. $194.95. 4.0 out of 5 stars

Low Stock

Brown Ariat Turbo Chelsea CSA Waterproof Carbon Toe Work Boots

Brown Ariat Turbo Chelsea CSA Waterproof Carbon Toe Work Boots

Brand Name: Ariat
Product Name: Turbo Chelsea CSA Waterproof Carbon Toe Work Boots
Gender: Men's
Color: Rich Brown
Price: $194.95
Rating: 4Rated 4 stars out of 5(11)

Bogs - Kicker Rain Chelsea Neo. Color Black 1. Low Stock. $100.00. 4.2 out of 5 stars

Low Stock

Black Bogs Kicker Rain Chelsea Neo

Black Bogs Kicker Rain Chelsea Neo

+3

Brand Name: Bogs
Product Name: Kicker Rain Chelsea Neo
Gender: Men's
Color: Black 1
Price: $100
Rating: 4Rated 4 stars out of 5(55)

Bogs - Arcata Urban Leather Chelsea. Color Chocolate 1. Low Stock. $150.00. 4.2 out of 5 stars

Low Stock

Tan Bogs Arcata Urban Leather Chelsea

Tan Bogs Arcata Urban Leather Chelsea

+3

Brand Name: Bogs
Product Name: Arcata Urban Leather Chelsea
Gender: Men's
Color: Chocolate 1
Price: $150
Rating: 4Rated 4 stars out of 5(39)

Carhartt - Millbrook 4" Romeo Soft Toe Wedge Boots. Color Brown Oil Tanned. Low Stock. On sale for $139.99. MSRP $144.99. 3% off. 3.6 out of 5 stars

Low Stock

Brown Carhartt Millbrook 4" Romeo Soft Toe Wedge Boots

Brown 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: Brown Oil Tanned
Price: $139.99MSRP: $144.993% OFF
Rating: 4Rated 4 stars out of 5(49)

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

Black Bogs Digger Slip-On

Black Bogs Digger Slip-On

+2

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

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(389)

Join Our Email List

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

*One code per email address.