GOING FAST
EXTRA 20% OFF*
Save on select styles with code EXTRA20
Shop Now
*Exclusions apply

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

Size 8 Medium Size Leather Chelsea Shoes

22 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(32)

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 - BL584. Color Rustic Brown. $239.95. 3.8 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(9)

Blundstone - BL2241. Color Black. $274.95. 4.4 out of 5 stars

Black Blundstone BL2241

Black Blundstone BL2241

Brand Name: Blundstone
Product Name: BL2241
Gender: Unisex
Color: Black
Price: $274.95
Rating: 4Rated 4 stars out of 5(8)

BRUNT - The Ohman Soft Toe. Color Black. $144.99. 4.1 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: $144.99
Rating: 4Rated 4 stars out of 5(7)

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)

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)

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(72)

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(38)

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)

Dr. Martens - 2976 Chelsea SR Boots. Color Black. On sale for $179.95. MSRP $190.00. 5% 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: $179.95MSRP: $1905% OFF
Rating: 4Rated 4 stars out of 5(76)

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

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)

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)

Tommy Hilfiger - Berton. Color Black. Low Stock. On sale for $59.50. MSRP $119.00. 50% 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: $59.50MSRP: $11950% OFF
Rating

. 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(87)

. Carhartt - Millbrook 4" Romeo Soft Toe Wedge Boots. Color Black Oil Tanned. On sale for $110.00. MSRP $144.99. 24% off. 3.5 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(57)

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(308)

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

Low Stock

Brown Twisted X 4" Work Chelsea Boot

Brown Twisted X 4" Work Chelsea Boot

+2

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

Cole Haan - Zerogrand Remastered Waterproof Chelsea Boots. Color Dark Coffee/Oxford Tan. On sale for $161.00. MSRP $230.00. 30% off.

Brown Cole Haan Zerogrand Remastered Waterproof Chelsea Boots

Brown Cole Haan Zerogrand Remastered Waterproof Chelsea Boots

Brand Name: Cole Haan
Product Name: Zerogrand Remastered Waterproof Chelsea Boots
Gender: Men's
Color: Dark Coffee/Oxford Tan
Price: $161MSRP: $23030% OFF
Rating

Bogs - Arcata Urban Leather Chelsea. Color Chocolate. Low Stock. $170.00. 4.2 out of 5 stars

Low Stock

Brown Bogs Arcata Urban Leather Chelsea

Brown Bogs Arcata Urban Leather Chelsea

+2

Brand Name: Bogs
Product Name: Arcata Urban Leather Chelsea
Gender: Men's
Color: Chocolate
Price: $170
Rating: 4Rated 4 stars out of 5(39)

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

Black L.L.Bean Storm Chaser Chelsea Boots

Black L.L.Bean Storm Chaser Chelsea Boots

+2

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

Join Our Email List

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

*One code per email address.