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

Medium Size Leather Chelsea Shoes

35 items found

Filters

Search Results

. Blundstone - BL587. Color Rustic Black. $209.95. 4.3 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(29)

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. 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)

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 - 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(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)

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)

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)

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)

Cole Haan - Hawthorne Chelsea Boots. Color Black. Low Stock. On sale for $142.80. MSRP $168.00. 15% off. 5.0 out of 5 stars

Low Stock

Black Cole Haan Hawthorne Chelsea Boots

Black Cole Haan Hawthorne Chelsea Boots

+2

Brand Name: Cole Haan
Product Name: Hawthorne Chelsea Boots
Gender: Men's
Color: Black
Price: $142.80MSRP: $16815% OFF
Rating: 5Rated 5 stars out of 5(3)

Barbour - Barbour Nimbus Chelsea Welly. Color Black. Low Stock. On sale for $100.00. MSRP $120.00. 17% off.

Low Stock

Black Barbour Barbour Nimbus Chelsea Welly

Black Barbour Barbour Nimbus Chelsea Welly

Brand Name: Barbour
Product Name: Barbour Nimbus Chelsea Welly
Gender: Men's
Color: Black
Price: $100MSRP: $12017% OFF
Rating

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

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)

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)

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)

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

Low Stock

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. $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)

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(141)

Tommy Hilfiger - Berton. Color Black. Low Stock. On sale for $89.25. MSRP $119.00. 25% 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: $89.25MSRP: $11925% OFF
Rating

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(12)

. 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(83)

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

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)

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(305)

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

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(11)

KEEN Utility - Lansing Chelsea Steel Toe. Color Dark Earth/Brindle. On sale for $144.95. 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: $144.95MSRP: $1503% OFF
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)

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

+2

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 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(52)

KEEN - Anchorage Boots III Waterproof. Color Dark Earth/Mulch. $175.00. 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: $175
Rating: 4Rated 4 stars out of 5(390)

Eastland 1955 Edition - Chimney Pond. Color Black. On sale for $87.00. MSRP $145.00. 40% off. 5.0 out of 5 stars

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: $87MSRP: $14540% OFF
Rating: 5Rated 5 stars out of 5(1)

Join Our Email List

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

*One code per email address.