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

Size 8.5 Elastic Comfort Boots

40 items found

Sort By

Your Selections

Search Results

Steve Madden - Hatford. Color Tan. $100.00.

Tan Steve Madden Hatford

Tan Steve Madden Hatford

+4

Brand Name: Steve Madden
Product Name: Hatford
Gender: Men's
Color: Tan
Price: $100.00
Rating

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: 5Rated 5 stars out of 5(18)

Steve Madden - Merrnie. Color Taupe. $79.99.

Taupe Steve Madden Merrnie

Taupe Steve Madden Merrnie

+2

Brand Name: Steve Madden
Product Name: Merrnie
Gender: Men's
Color: Taupe
Price: $79.99
Rating

SOREL - Cyprus Chelsea Waterproof. Color Khaki Ii/Jet. $125.00.

Khaki SOREL Cyprus Chelsea Waterproof

Khaki SOREL Cyprus Chelsea Waterproof

+3

Brand Name: SOREL
Product Name: Cyprus Chelsea Waterproof
Gender: Men's
Color: Khaki Ii/Jet
Price: $125.00
Rating

Clarks - Shepton Easy. Color Beeswax Leather. $130.00. 5.0 out of 5 stars

Brown Clarks Shepton Easy

Brown Clarks Shepton Easy

Brand Name: Clarks
Product Name: Shepton Easy
Gender: Men's
Color: Beeswax Leather
Price: $130.00
Rating

Florsheim - Lodge Plain Toe Gore Boot. Color Black Crazy Horse. $144.95. 4.4 out of 5 stars

Black Florsheim Lodge Plain Toe Gore Boot

Black Florsheim Lodge Plain Toe Gore Boot

+3

Brand Name: Florsheim
Product Name: Lodge Plain Toe Gore Boot
Gender: Men's
Color: Black Crazy Horse
Price: $144.95
Rating: 4Rated 4 stars out of 5(112)

Nunn Bush - Otis 2.0 Chelsea Fashion Leather Boot. Color Tan. On sale for $89.95. MSRP $120.00. 25% off. 4.3 out of 5 stars

Tan Nunn Bush Otis 2.0 Chelsea Fashion Leather Boot

Tan Nunn Bush Otis 2.0 Chelsea Fashion Leather Boot

+3

Brand Name: Nunn Bush
Product Name: Otis 2.0 Chelsea Fashion Leather Boot
Gender: Men's
Color: Tan
Price: $89.95MSRP: $120.0025% OFF
Rating: 4Rated 4 stars out of 5(7)

To Boot New York - Christophe. Color Black. On sale for $445.50. MSRP $495.00. 10% off.

Black To Boot New York Christophe

Black To Boot New York Christophe

+3

Brand Name: To Boot New York
Product Name: Christophe
Gender: Men's
Color: Black
Price: $445.50MSRP: $495.0010% OFF
Rating

Deer Stags - Rockland. Color Redwood/Dark Brown. On sale for $64.99. MSRP $90.00. 28% off. 3.7 out of 5 stars

Brown Deer Stags Rockland

Brown Deer Stags Rockland

+1

Brand Name: Deer Stags
Product Name: Rockland
Gender: Men's
Color: Redwood/Dark Brown
Price: $64.99MSRP: $90.0028% OFF
Rating: 4Rated 4 stars out of 5(31)

Johnston & Murphy - Calder Chelsea Boots. Color Snuff Waxed Suede. $178.95.

Brown Johnston & Murphy Calder Chelsea Boots

Brown Johnston & Murphy Calder Chelsea Boots

Brand Name: Johnston & Murphy
Product Name: Calder Chelsea Boots
Gender: Men's
Color: Snuff Waxed Suede
Price: $178.95
Rating

Red Wing Heritage - Classic Chelsea. Color Black Harness. On sale for $298.95. MSRP $329.99. 9% off. 4.3 out of 5 stars

Black Red Wing Heritage Classic Chelsea

Black Red Wing Heritage Classic Chelsea

+3

Brand Name: Red Wing Heritage
Product Name: Classic Chelsea
Gender: Men's
Color: Black Harness
Price: $298.95MSRP: $329.999% OFF
Rating: 4Rated 4 stars out of 5(15)

Bogs - Arcata Urban Leather Chelsea. Color Black 1. Low Stock. $150.00. 4.3 out of 5 stars

Low Stock

Black Bogs Arcata Urban Leather Chelsea

Black Bogs Arcata Urban Leather Chelsea

+4

Brand Name: Bogs
Product Name: Arcata Urban Leather Chelsea
Gender: Men's
Color: Black 1
Price: $150.00
Rating: 4Rated 4 stars out of 5(35)

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: $170.00
Rating: 4Rated 4 stars out of 5(31)

L.L.Bean - Bean Boot 6.5" Chelsea. Color Black/Warm Grey Opaque. $160.00. 3.0 out of 5 stars

Black L.L.Bean Bean Boot 6.5" Chelsea

Black L.L.Bean Bean Boot 6.5" Chelsea

+1

Brand Name: L.L.Bean
Product Name: Bean Boot 6.5" Chelsea
Gender: Men's
Color: Black/Warm Grey Opaque
Price: $160.00
Rating: 3Rated 3 stars out of 5(114)

Johnston & Murphy - XC Flex Raleigh Chelsea. Color Tan Full Grain. $184.95. 4.4 out of 5 stars

Tan Johnston & Murphy XC Flex Raleigh Chelsea

Tan Johnston & Murphy XC Flex Raleigh Chelsea

Brand Name: Johnston & Murphy
Product Name: XC Flex Raleigh Chelsea
Gender: Men's
Color: Tan Full Grain
Price: $184.95
Rating: 4Rated 4 stars out of 5(69)

SOREL - Carson™ Chelsea Waterproof. Color Brown. On sale for $82.15. MSRP $155.00. 47% off. 1.0 out of 5 stars

Brown SOREL Carson™ Chelsea Waterproof

Brown SOREL Carson™ Chelsea Waterproof

Brand Name: SOREL
Product Name: Carson™ Chelsea Waterproof
Gender: Men's
Color: Brown
Price: $82.15MSRP: $155.0047% OFF
Rating: 1Rated 1 star out of 5(1)

Deer Stags - Argos. Color Black/Blue. On sale for $51.00. MSRP $100.00. 49% off. 3.7 out of 5 stars

Black Deer Stags Argos

Black Deer Stags Argos

Brand Name: Deer Stags
Product Name: Argos
Gender: Men's
Color: Black/Blue
Price: $51.00MSRP: $100.0049% OFF
Rating: 4Rated 4 stars out of 5(24)

Carhartt - Frontier 6" Water Resistant Boot. Color Mossy Brown. $129.99. 4.2 out of 5 stars

Brown Carhartt Frontier 6" Water Resistant Boot

Brown Carhartt Frontier 6" Water Resistant Boot

Brand Name: Carhartt
Product Name: Frontier 6" Water Resistant Boot
Gender: Men's
Color: Mossy Brown
Price: $129.99
Rating: 4Rated 4 stars out of 5(6)

Stacy Adams - Thompson Elastic Lace Inside Zip Boots. Color Black. $150.00.

Black Stacy Adams Thompson Elastic Lace Inside Zip Boots

Black Stacy Adams Thompson Elastic Lace Inside Zip Boots

+2

Brand Name: Stacy Adams
Product Name: Thompson Elastic Lace Inside Zip Boots
Gender: Men's
Color: Black
Price: $150.00
Rating

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

Gray Forsake Phil Chelsea

Gray Forsake Phil Chelsea

+3

Brand Name: Forsake
Product Name: Phil Chelsea
Gender: Men's
Color: Gray
Price: $145.00
Rating: 4Rated 4 stars out of 5(43)

Ariat - Midtown Rambler Boots. Color Matte Black. $169.95. 4.4 out of 5 stars

Black Ariat Midtown Rambler Boots

Black Ariat Midtown Rambler Boots

Brand Name: Ariat
Product Name: Midtown Rambler Boots
Gender: Men's
Color: Matte Black
Price: $169.95
Rating: 4Rated 4 stars out of 5(23)

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: $180.008% OFF
Rating: 4Rated 4 stars out of 5(73)

Tommy Hilfiger - Vitus. Color Black. On sale for $80.16. MSRP $119.00. 33% off.

Black Tommy Hilfiger Vitus

Black Tommy Hilfiger Vitus

Brand Name: Tommy Hilfiger
Product Name: Vitus
Gender: Men's
Color: Black
Price: $80.16MSRP: $119.0033% OFF
Rating

Caterpillar - Threshold Rebound Chelsea WP ST. Color Bison. $144.95.

Brown Caterpillar Threshold Rebound Chelsea WP ST

Brown Caterpillar Threshold Rebound Chelsea WP ST

Brand Name: Caterpillar
Product Name: Threshold Rebound Chelsea WP ST
Gender: Men's
Color: Bison
Price: $144.95
Rating

Carhartt - Force Wr 4" Romeo Soft Toe Boot. Color Black Oil Tanned. $139.99. 3.0 out of 5 stars

Black Carhartt Force Wr 4" Romeo Soft Toe Boot

Black Carhartt Force Wr 4" Romeo Soft Toe Boot

Brand Name: Carhartt
Product Name: Force Wr 4" Romeo Soft Toe Boot
Gender: Men's
Color: Black Oil Tanned
Price: $139.99
Rating: 3Rated 3 stars out of 5(5)

Columbia - Landroamer Scout Nubuck. Color Black/Canyon Sun. On sale for $74.37. MSRP $100.00. 26% off. 3.0 out of 5 stars

Black Columbia Landroamer Scout Nubuck

Black Columbia Landroamer Scout Nubuck

Brand Name: Columbia
Product Name: Landroamer Scout Nubuck
Gender: Men's
Color: Black/Canyon Sun
Price: $74.37MSRP: $100.0026% OFF
Rating: 3Rated 3 stars out of 5(2)

Eastland 1955 Edition - Daily Double. Color Brown Nubuck. On sale for $82.32. MSRP $125.00. 34% off. 3.4 out of 5 stars

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: $82.32MSRP: $125.0034% OFF
Rating: 3Rated 3 stars out of 5(14)

L.L.Bean - Stonington Chelsea Boot Suede. Color Deepest Brown. $138.95. 3.6 out of 5 stars

Brown L.L.Bean Stonington Chelsea Boot Suede

Brown L.L.Bean Stonington Chelsea Boot Suede

Brand Name: L.L.Bean
Product Name: Stonington Chelsea Boot Suede
Gender: Men's
Color: Deepest Brown
Price: $138.95
Rating: 4Rated 4 stars out of 5(5)

. Stacy Adams - Eastmont Elastic Lace Boots. Color Black. $140.00.

Black Stacy Adams Eastmont Elastic Lace Boots

Black Stacy Adams Eastmont Elastic Lace Boots

+3

Brand Name: Stacy Adams
Product Name: Eastmont Elastic Lace Boots
Gender: Men's
Color: Black
Price: $140.00
Rating

. Ariat - Wexford Waterproof Chelsea Boot. Color Palm Brown. $209.95.

Brown Ariat Wexford Waterproof Chelsea Boot

Brown Ariat Wexford Waterproof Chelsea Boot

Brand Name: Ariat
Product Name: Wexford Waterproof Chelsea Boot
Gender: Men's
Color: Palm Brown
Price: $209.95
Rating

Nunn Bush - 1912 Plain Toe Chelsea Boot. Color Black. Low Stock. On sale for $59.90. MSRP $115.00. 48% off. 3.9 out of 5 stars

Low Stock

Black Nunn Bush 1912 Plain Toe Chelsea Boot

Black Nunn Bush 1912 Plain Toe Chelsea Boot

Brand Name: Nunn Bush
Product Name: 1912 Plain Toe Chelsea Boot
Gender: Men's
Color: Black
Price: $59.90MSRP: $115.0048% OFF
Rating: 4Rated 4 stars out of 5(14)

Pajar CANADA - Fortuo 2.0. Color Cognac/Black. Low Stock. $209.95.

Low Stock

Burgundy Pajar CANADA Fortuo 2.0

Burgundy Pajar CANADA Fortuo 2.0

+2

Brand Name: Pajar CANADA
Product Name: Fortuo 2.0
Gender: Men's
Color: Cognac/Black
Price: $209.95
Rating

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

Low Stock

Brown Allen Edmonds Liverpool

Brown Allen Edmonds Liverpool

+4

Brand Name: Allen Edmonds
Product Name: Liverpool
Gender: Men's
Color: Chili
Price: $550.00
Rating: 4Rated 4 stars out of 5(154)

Nunn Bush - Otis Plain Toe Chelsea Boot with KORE Walking Comfort Technology. Color Brown CH. On sale for $102.35. MSRP $115.00. 11% off. 4.2 out of 5 stars

Brown Nunn Bush Otis Plain Toe Chelsea Boot with KORE Walking Comfort Technology

Brown Nunn Bush Otis Plain Toe Chelsea Boot with KORE Walking Comfort Technology

+3

Brand Name: Nunn Bush
Product Name: Otis Plain Toe Chelsea Boot with KORE Walking Comfort Technology
Gender: Men's
Color: Brown CH
Price: $102.35MSRP: $115.0011% OFF
Rating: 4Rated 4 stars out of 5(102)

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(294)

Born - Brody. Color Taupe Dist. $150.00. 4.7 out of 5 stars

Taupe Born Brody

Taupe Born Brody

Brand Name: Born
Product Name: Brody
Gender: Men's
Color: Taupe Dist
Price: $150.00
Rating: 5Rated 5 stars out of 5(27)

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

Brown Born Hemlock

Brown Born Hemlock

+2

Brand Name: Born
Product Name: Hemlock
Gender: Men's
Color: Brown Full Grain
Price: $145.00
Rating: 4Rated 4 stars out of 5(189)

KEEN - Anchorage Boot III Waterproof. Color Dark Earth/Mulch. $174.95. 4.0 out of 5 stars

Brown KEEN Anchorage Boot III Waterproof

Brown KEEN Anchorage Boot III Waterproof

+2

Brand Name: KEEN
Product Name: Anchorage Boot III Waterproof
Gender: Men's
Color: Dark Earth/Mulch
Price: $174.95
Rating: 4Rated 4 stars out of 5(385)

Mephisto - Benson. Color Moss. Low Stock. On sale for $202.05. MSRP $449.00. 55% off. 5.0 out of 5 stars

Low Stock

Green Mephisto Benson

Green Mephisto Benson

Brand Name: Mephisto
Product Name: Benson
Gender: Men's
Color: Moss
Price: $202.05MSRP: $449.0055% OFF
Rating: 5Rated 5 stars out of 5(4)

Polo Ralph Lauren - Bryson Chelsea Boot. Color Brown 1. $228.00. 3.8 out of 5 stars

Brown Polo Ralph Lauren Bryson Chelsea Boot

Brown Polo Ralph Lauren Bryson Chelsea Boot

Brand Name: Polo Ralph Lauren
Product Name: Bryson Chelsea Boot
Gender: Men's
Color: Brown 1
Price: $228.00
Rating: 4Rated 4 stars out of 5(4)

Join Our List, Get 10% Off

Sign up for Zappos emails—new subscribers get 10% off a future order!* Plus, get early access to sales, coupons, and more. (One code per email address.)