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 9 Ankle Chelsea Products

34 items found

Filters

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)

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)

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)

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)

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)

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)

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

Carhartt - Wedge 5" Chelsea Pull-On Boot Soft Toe. Color Dark Bison Oil Tanned. Low Stock. $149.99. 3.6 out of 5 stars

Low Stock

Brown Carhartt Wedge 5" Chelsea Pull-On Boot Soft Toe

Brown Carhartt Wedge 5" Chelsea Pull-On Boot Soft Toe

Brand Name: Carhartt
Product Name: Wedge 5" Chelsea Pull-On Boot Soft Toe
Gender: Men's
Color: Dark Bison Oil Tanned
Price: $149.99
Rating: 4Rated 4 stars out of 5(31)

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

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 - Arcata Urban Leather Chelsea. Color Chocolate. On sale for $155.00. MSRP $170.00. 9% off. 4.2 out of 5 stars

Brown Bogs Arcata Urban Leather Chelsea

Brown Bogs Arcata Urban Leather Chelsea

+3

Brand Name: Bogs
Product Name: Arcata Urban Leather Chelsea
Gender: Men's
Color: Chocolate
Price: $155MSRP: $1709% OFF
Rating: 4Rated 4 stars out of 5(39)

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)

Bogs - Kicker Rain Chelsea Neo. Color Dark Green Multi. $109.95. 4.2 out of 5 stars

Green Bogs Kicker Rain Chelsea Neo

Green Bogs Kicker Rain Chelsea Neo

+3

Brand Name: Bogs
Product Name: Kicker Rain Chelsea Neo
Gender: Men's
Color: Dark Green Multi
Price: $109.95
Rating: 4Rated 4 stars out of 5(55)

BRUNT - The Ohman Comp Toe. Color Black. $149.99. 3.7 out of 5 stars

Black BRUNT The Ohman Comp Toe

Black BRUNT The Ohman Comp Toe

+2

Brand Name: BRUNT
Product Name: The Ohman Comp Toe
Gender: Men's
Color: Black
Price: $149.99
Rating: 4Rated 4 stars out of 5(15)

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)

. 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)

ALDO - Bristoll-Wide. Color Brown. On sale for $119.05. MSRP $140.00. 15% off.

Brown ALDO Bristoll-Wide

Brown ALDO Bristoll-Wide

Brand Name: ALDO
Product Name: Bristoll-Wide
Gender: Men's
Color: Brown
Price: $119.05MSRP: $14015% OFF
Rating

Join Our Email List

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

*One code per email address.