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

Medium Size Stretch Leather Shoes

49 items found

Filters

Search Results

Dr. Martens - Embury. Color Gunmetal. $130.00. 4.0 out of 5 stars

Gray Dr. Martens Embury

Gray Dr. Martens Embury

+3

Brand Name: Dr. Martens
Product Name: Embury
Gender: Unisex
Color: Gunmetal
Price: $130
Rating: 4Rated 4 stars out of 5(122)

Merrell - Moab Adventure 3 Chelsea Wp. Color Earth. $170.00. 2.9 out of 5 stars

Brown Merrell Moab Adventure 3 Chelsea Wp

Brown Merrell Moab Adventure 3 Chelsea Wp

+2

Brand Name: Merrell
Product Name: Moab Adventure 3 Chelsea Wp
Gender: Men's
Color: Earth
Price: $170
Rating: 3Rated 3 stars out of 5(9)

Florsheim - Lodge Plain Toe Gore Boots. Color Chestnut Smooth. $145.00. 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: $145
Rating: 4Rated 4 stars out of 5(126)

Born - Hemlock. Color Black Full Grain. $145.00. 4.3 out of 5 stars

Black Born Hemlock

Black Born Hemlock

+2

Brand Name: Born
Product Name: Hemlock
Gender: Men's
Color: Black Full Grain
Price: $145
Rating: 4Rated 4 stars out of 5(191)

Birkenstock - Highwood Deep Blue. Color Graphite. $200.00. 4.2 out of 5 stars

Gray Birkenstock Highwood Deep Blue

Gray Birkenstock Highwood Deep Blue

+4

Brand Name: Birkenstock
Product Name: Highwood Deep Blue
Gender: Men's
Color: Graphite
Price: $200
Rating: 4Rated 4 stars out of 5(9)

Ariat - Wexford Waterproof. Color Black. $209.95. 4.5 out of 5 stars

Black Ariat Wexford Waterproof

Black Ariat Wexford Waterproof

+2

Brand Name: Ariat
Product Name: Wexford Waterproof
Gender: Men's
Color: Black
Price: $209.95
Rating: 4Rated 4 stars out of 5(262)

Johnston & Murphy - Upton Chelsea. Color Brown Oiled Full Grain. Low Stock. On sale for $119.99. MSRP $179.00. 33% off. 4.4 out of 5 stars

Low Stock

Brown Johnston & Murphy Upton Chelsea

Brown Johnston & Murphy Upton Chelsea

Brand Name: Johnston & Murphy
Product Name: Upton Chelsea
Gender: Men's
Color: Brown Oiled Full Grain
Price: $119.99MSRP: $17933% OFF
Rating: 4Rated 4 stars out of 5(203)

Dr. Martens - 2976 Yellow Stitch Smooth Leather Chelsea Boots. Color Black Smooth. $179.95. 3.8 out of 5 stars

Black Dr. Martens 2976 Yellow Stitch Smooth Leather Chelsea Boots

Black Dr. Martens 2976 Yellow Stitch Smooth Leather Chelsea Boots

+2

Brand Name: Dr. Martens
Product Name: 2976 Yellow Stitch Smooth Leather Chelsea Boots
Gender: Unisex
Color: Black Smooth
Price: $179.95
Rating: 4Rated 4 stars out of 5(44)

Bogs - Spruce Chelsea. Color Dark Brown. $149.95. 3.7 out of 5 stars

Brown Bogs Spruce Chelsea

Brown Bogs Spruce Chelsea

+3

Brand Name: Bogs
Product Name: Spruce Chelsea
Gender: Men's
Color: Dark Brown
Price: $149.95
Rating: 4Rated 4 stars out of 5(44)

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(390)

Dr. Martens - 2976 Quad Smooth Leather Platform Chelsea Boots. Color Black Polished Smooth. On sale for $189.00. MSRP $210.00. 10% off. 4.2 out of 5 stars

Black Dr. Martens 2976 Quad Smooth Leather Platform Chelsea Boots

Black Dr. Martens 2976 Quad Smooth Leather Platform Chelsea Boots

Brand Name: Dr. Martens
Product Name: 2976 Quad Smooth Leather Platform Chelsea Boots
Gender: Unisex
Color: Black Polished Smooth
Price: $189MSRP: $21010% OFF
Rating: 4Rated 4 stars out of 5(34)

Johnston & Murphy - XC+ Durham Chelsea Boots. Color Black Waterproof Full Grain. $218.95.

Black Johnston & Murphy XC+ Durham Chelsea Boots

Black Johnston & Murphy XC+ Durham Chelsea Boots

+2

Brand Name: Johnston & Murphy
Product Name: XC+ Durham Chelsea Boots
Gender: Men's
Color: Black Waterproof Full Grain
Price: $218.95
Rating

Twisted X - MDMG002. Color Bomber. $144.95. 5.0 out of 5 stars

Bone Twisted X MDMG002

Bone Twisted X MDMG002

Brand Name: Twisted X
Product Name: MDMG002
Gender: Men's
Color: Bomber
Price: $144.95
Rating: 5Rated 5 stars out of 5(1)

Born - Brody. Color Taupe Dist. $150.00. 4.6 out of 5 stars

Taupe Born Brody

Taupe Born Brody

Brand Name: Born
Product Name: Brody
Gender: Men's
Color: Taupe Dist
Price: $150
Rating: 5Rated 5 stars out of 5(29)

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)

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)

Red Wing Heritage - Classic Chelsea. Color Hawthorne Muleskinner. Low Stock. $299.99. 4.1 out of 5 stars

Low Stock

Khaki Red Wing Heritage Classic Chelsea

Khaki Red Wing Heritage Classic Chelsea

+3

Brand Name: Red Wing Heritage
Product Name: Classic Chelsea
Gender: Men's
Color: Hawthorne Muleskinner
Price: $299.99
Rating: 4Rated 4 stars out of 5(16)

Ariat - Hybrid Low Western Boots. Color Stone. $159.95. 4.4 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(163)

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)

Ariat - Booker Ultra Square Toe Western Boots. Color Black Deertan. $149.95. 4.4 out of 5 stars

Black Ariat Booker Ultra Square Toe Western Boots

Black Ariat Booker Ultra Square Toe Western Boots

+3

Brand Name: Ariat
Product Name: Booker Ultra Square Toe Western Boots
Gender: Men's
Color: Black Deertan
Price: $149.95
Rating: 4Rated 4 stars out of 5(109)

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)

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)

. Nisolo - All-Weather Chelsea Boot. Color Dark Tobacco. On sale for $104.00. MSRP $260.00. 60% off. 1.5 out of 5 stars

Red Nisolo All-Weather Chelsea Boot

Red Nisolo All-Weather Chelsea Boot

Brand Name: Nisolo
Product Name: All-Weather Chelsea Boot
Gender: Men's
Color: Dark Tobacco
Price: $104MSRP: $26060% OFF
Rating: 2Rated 2 stars out of 5(2)

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

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 - 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(142)

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)

Forsake - Phil Chelsea. Color Gray. Low Stock. $145.00. 4.0 out of 5 stars

Low Stock

Gray Forsake Phil Chelsea

Gray Forsake Phil Chelsea

+3

Brand Name: Forsake
Product Name: Phil Chelsea
Gender: Men's
Color: Gray
Price: $145
Rating: 4Rated 4 stars out of 5(47)

Johnston & Murphy - XC Flex Raleigh Chelsea. Color Black Full Grain. $185.00. 4.4 out of 5 stars

Black Johnston & Murphy XC Flex Raleigh Chelsea

Black Johnston & Murphy XC Flex Raleigh Chelsea

Brand Name: Johnston & Murphy
Product Name: XC Flex Raleigh Chelsea
Gender: Men's
Color: Black Full Grain
Price: $185
Rating: 4Rated 4 stars out of 5(69)

. 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)

Allen Edmonds - Liverpool. Color Chili. $550.00. 4.3 out of 5 stars

Brown Allen Edmonds Liverpool

Brown Allen Edmonds Liverpool

+4

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

Wolverine - Alpha Ft Wolverine Infinity System Carbonmax® Slip-on Work Romeo. Color Black. $174.95. 3.0 out of 5 stars

Black Wolverine Alpha Ft Wolverine Infinity System Carbonmax® Slip-on Work Romeo

Black Wolverine Alpha Ft Wolverine Infinity System Carbonmax® Slip-on Work Romeo

Brand Name: Wolverine
Product Name: Alpha Ft Wolverine Infinity System Carbonmax® Slip-on Work Romeo
Gender: Men's
Color: Black
Price: $174.95
Rating: 3Rated 3 stars out of 5(2)

SAS - Premier Work Non-Slip Pull-On Comfort Boots. Color Black. $298.95.

Black SAS Premier Work Non-Slip Pull-On Comfort Boots

Black SAS Premier Work Non-Slip Pull-On Comfort Boots

Brand Name: SAS
Product Name: Premier Work Non-Slip Pull-On Comfort Boots
Gender: Men's
Color: Black
Price: $298.95
Rating

Ariat - Turbo Chelsea Waterproof Carbon Toe EH. Color Aged Bark. Low Stock. $174.95. 4.3 out of 5 stars

Low Stock

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)

Carhartt - Millbrook 4" Romeo Steel Toe Wedge Work Boots. Color Brown Oil Tanned. $149.99. 4.2 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(13)

Steve Madden - Duke. Color Cognac Leather. On sale for $98.00. MSRP $140.00. 30% off. 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: $98MSRP: $14030% OFF
Rating: 5Rated 5 stars out of 5(1)

Polo Ralph Lauren - Bryson Chelsea Boot. Color Black Dress Calf. Low Stock. $198.00. 3.8 out of 5 stars

Low Stock

Black Polo Ralph Lauren Bryson Chelsea Boot

Black Polo Ralph Lauren Bryson Chelsea Boot

Brand Name: Polo Ralph Lauren
Product Name: Bryson Chelsea Boot
Gender: Men's
Color: Black Dress Calf
Price: $198
Rating: 4Rated 4 stars out of 5(4)

Dr. Martens - 2976 Smooth Leather Chelsea Boots. Color Black Smooth. Low Stock. $169.95. 4.0 out of 5 stars

Low Stock

Black Dr. Martens 2976 Smooth Leather Chelsea Boots

Black Dr. Martens 2976 Smooth Leather Chelsea Boots

Brand Name: Dr. Martens
Product Name: 2976 Smooth Leather Chelsea Boots
Gender: Unisex
Color: Black Smooth
Price: $169.95
Rating: 4Rated 4 stars out of 5(72)

Blundstone - BL1477 Waterproof Winter Chelsea Boot. Color Antique Brown. Low Stock. $239.95. 4.5 out of 5 stars

Low Stock

Brown Blundstone BL1477 Waterproof Winter Chelsea Boot

Brown Blundstone BL1477 Waterproof Winter Chelsea Boot

Brand Name: Blundstone
Product Name: BL1477 Waterproof Winter Chelsea Boot
Gender: Unisex
Color: Antique Brown
Price: $239.95
Rating: 5Rated 5 stars out of 5(30)

Eastland 1955 Edition - Daily Double. Color Brown Nubuck. Low Stock. On sale for $87.50. MSRP $125.00. 30% off. 3.4 out of 5 stars

Low Stock

Brown Eastland 1955 Edition Daily Double

Brown Eastland 1955 Edition Daily Double

+3

Brand Name: Eastland 1955 Edition
Product Name: Daily Double
Gender: Men's
Color: Brown Nubuck
Price: $87.50MSRP: $12530% OFF
Rating: 3Rated 3 stars out of 5(14)

Steve Madden - Sverne. Color Tan Leather. Low Stock. $150.00. 3.0 out of 5 stars

Low Stock

Tan Steve Madden Sverne

Tan Steve Madden Sverne

Brand Name: Steve Madden
Product Name: Sverne
Gender: Men's
Color: Tan Leather
Price: $150
Rating: 3Rated 3 stars out of 5(1)

Naot - Business. Color French Roast Leather/Saddle Brown Leather/Seal Brown Suede. Low Stock. On sale for $149.97. MSRP $249.95. 40% off. 4.6 out of 5 stars

Low Stock

Black Naot Business

Black Naot Business

Brand Name: Naot
Product Name: Business
Gender: Men's
Color: French Roast Leather/Saddle Brown Leather/Seal Brown Suede
Price: $149.97MSRP: $249.9540% OFF
Rating: 5Rated 5 stars out of 5(36)

Merrell - Moab 3 Mid Waterproof. Color Grey Stone. $170.00. 4.4 out of 5 stars

Gray Merrell Moab 3 Mid Waterproof

Gray Merrell Moab 3 Mid Waterproof

+9

Brand Name: Merrell
Product Name: Moab 3 Mid Waterproof
Gender: Men's
Color: Grey Stone
Price: $170
Rating: 4Rated 4 stars out of 5(571)

Dansko - Frankie. Color Black Oiled. $179.95. 4.2 out of 5 stars

Black Dansko Frankie

Black Dansko Frankie

+3

Brand Name: Dansko
Product Name: Frankie
Gender: Women's
Color: Black Oiled
Price: $179.95
Rating: 4Rated 4 stars out of 5(309)

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

Low Stock

Black Cole Haan Roundhill Grand Chelsea Boots

Black Cole Haan Roundhill Grand Chelsea Boots

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)

Marc Joseph New York - Austin. Color Cognac Grainy. On sale for $89.95. MSRP $195.00. 54% off. 4.1 out of 5 stars

Brown Marc Joseph New York Austin

Brown Marc Joseph New York Austin

Brand Name: Marc Joseph New York
Product Name: Austin
Gender: Men's
Color: Cognac Grainy
Price: $89.95MSRP: $19554% OFF
Rating: 4Rated 4 stars out of 5(9)

Merrell - Alpine 83 Sneaker Recraft Mid Waterproof. Color Charcoal. Low Stock. On sale for $124.16. MSRP $125.00. 1% off. 3.4 out of 5 stars

Low Stock

Black Merrell Alpine 83 Sneaker Recraft Mid Waterproof

Black Merrell Alpine 83 Sneaker Recraft Mid Waterproof

Brand Name: Merrell
Product Name: Alpine 83 Sneaker Recraft Mid Waterproof
Gender: Men's
Color: Charcoal
Price: $124.16MSRP: $1251% OFF
Rating: 3Rated 3 stars out of 5(5)

Join Our Email List

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

*One code per email address.