Introducing
Zappos In Motion
Sneakers & gear curated by performance experts connecting their communities through movement.
Shop Their Picks

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

Size 8.5 Ankle Elastic Products

53 items found

Filters

Search Results

Marc Joseph New York - Hudson Yards 2.0 (Hands Free Technology). Color Cognac Napa Leather. On sale for $109.95. MSRP $195.00. 44% off. 5.0 out of 5 stars

Brown Marc Joseph New York Hudson Yards 2.0 (Hands Free Technology)

Brown Marc Joseph New York Hudson Yards 2.0 (Hands Free Technology)

+4

Brand Name: Marc Joseph New York
Product Name: Hudson Yards 2.0 (Hands Free Technology)
Gender: Men's
Color: Cognac Napa Leather
Price: $109.95MSRP: $19544% OFF
Rating: 5Rated 5 stars out of 5(3)

Nunn Bush - Karnak Plain Toe Chelsea Boots Lightweight Comfortable Chukka. Color Tan. On sale for $89.95. MSRP $120.00. 25% off. 5.0 out of 5 stars

Tan Nunn Bush Karnak Plain Toe Chelsea Boots Lightweight Comfortable Chukka

Tan Nunn Bush Karnak Plain Toe Chelsea Boots Lightweight Comfortable Chukka

+2

Brand Name: Nunn Bush
Product Name: Karnak Plain Toe Chelsea Boots Lightweight Comfortable Chukka
Gender: Men's
Color: Tan
Price: $89.95MSRP: $12025% OFF
Rating: 5Rated 5 stars out of 5(2)

Nunn Bush - Otis 2.0 Chelsea Fashion Leather Boots. Color Black. On sale for $89.95. MSRP $120.00. 25% off. 4.2 out of 5 stars

Black Nunn Bush Otis 2.0 Chelsea Fashion Leather Boots

Black Nunn Bush Otis 2.0 Chelsea Fashion Leather Boots

+3

Brand Name: Nunn Bush
Product Name: Otis 2.0 Chelsea Fashion Leather Boots
Gender: Men's
Color: Black
Price: $89.95MSRP: $12025% OFF
Rating: 4Rated 4 stars out of 5(9)

Blundstone - Original Suede Chelsea Boots. Color Steel Grey. $184.95. 5.0 out of 5 stars

Gray Blundstone Original Suede Chelsea Boots

Gray Blundstone Original Suede Chelsea Boots

+2

Brand Name: Blundstone
Product Name: Original Suede Chelsea Boots
Gender: Unisex
Color: Steel Grey
Price: $184.95
Rating: 5Rated 5 stars out of 5(1)

Stacy Adams - Eastmont Elastic Lace Boots. Color White. Low Stock. On sale for $126.00. MSRP $140.00. 10% off. 4.0 out of 5 stars

Low Stock

White Stacy Adams Eastmont Elastic Lace Boots

White Stacy Adams Eastmont Elastic Lace Boots

+3

Brand Name: Stacy Adams
Product Name: Eastmont Elastic Lace Boots
Gender: Men's
Color: White
Price: $126MSRP: $14010% OFF
Rating: 4Rated 4 stars out of 5(1)

. Steve Madden - Highline. Color Tobacco Suede. On sale for $107.06. MSRP $109.95. 3% off. 4.2 out of 5 stars

Brown Steve Madden Highline

Brown Steve Madden Highline

+4

Brand Name: Steve Madden
Product Name: Highline
Gender: Men's
Color: Tobacco Suede
Price: $107.06MSRP: $109.953% OFF
Rating: 4Rated 4 stars out of 5(22)

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)

Florsheim - Forge Plain Toe Gore Boots. Color Brown Crazy Horse. $130.00. 4.1 out of 5 stars

Brown Florsheim Forge Plain Toe Gore Boots

Brown Florsheim Forge Plain Toe Gore Boots

+3

Brand Name: Florsheim
Product Name: Forge Plain Toe Gore Boots
Gender: Men's
Color: Brown Crazy Horse
Price: $130
Rating: 4Rated 4 stars out of 5(19)

Tommy Hilfiger - Sesame. Color Black. On sale for $62.68. MSRP $119.00. 47% off. 5.0 out of 5 stars

Black Tommy Hilfiger Sesame

Black Tommy Hilfiger Sesame

+2

Brand Name: Tommy Hilfiger
Product Name: Sesame
Gender: Men's
Color: Black
Price: $62.68MSRP: $11947% OFF
Rating: 5Rated 5 stars out of 5(6)

Sperry - Clifton Boots. Color Olive. On sale for $104.99. MSRP $110.00. 5% off. 5.0 out of 5 stars

Olive Sperry Clifton Boots

Olive Sperry Clifton Boots

+2

Brand Name: Sperry
Product Name: Clifton Boots
Gender: Men's
Color: Olive
Price: $104.99MSRP: $1105% OFF
Rating: 5Rated 5 stars out of 5(1)

Steve Madden - Hatford. Color Black. On sale for $87.41. MSRP $100.00. 13% off.

Black Steve Madden Hatford

Black Steve Madden Hatford

+4

Brand Name: Steve Madden
Product Name: Hatford
Gender: Men's
Color: Black
Price: $87.41MSRP: $10013% OFF
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)

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)

Steve Madden - Merrnie - Madden by Steve Madden. Color Tan. On sale for $63.99. MSRP $79.99. 20% off.

Tan Steve Madden Merrnie - Madden by Steve Madden

Tan Steve Madden Merrnie - Madden by Steve Madden

+2

Brand Name: Steve Madden
Product Name: Merrnie - Madden by Steve Madden
Gender: Men's
Color: Tan
Price: $63.99MSRP: $79.9920% OFF
Rating

Deer Stags - Brayden. Color Black. On sale for $70.00. MSRP $100.00. 30% off. 3.3 out of 5 stars

Black Deer Stags Brayden

Black Deer Stags Brayden

+2

Brand Name: Deer Stags
Product Name: Brayden
Gender: Men's
Color: Black
Price: $70MSRP: $10030% OFF
Rating: 3Rated 3 stars out of 5(3)

Ariat - Hybrid Low Western Boots. Color Stone. $159.95. 4.5 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(147)

Kenneth Cole - Tully Chelsea Boots. Color Black Leather. On sale for $166.45. MSRP $184.95. 10% off.

Black Kenneth Cole Tully Chelsea Boots

Black Kenneth Cole Tully Chelsea Boots

Brand Name: Kenneth Cole
Product Name: Tully Chelsea Boots
Gender: Men's
Color: Black Leather
Price: $166.45MSRP: $184.9510% OFF
Rating

Deer Stags - Rockland. Color Black/Black. On sale for $70.00. MSRP $90.00. 22% off. 3.7 out of 5 stars

Black Deer Stags Rockland

Black Deer Stags Rockland

+1

Brand Name: Deer Stags
Product Name: Rockland
Gender: Men's
Color: Black/Black
Price: $70MSRP: $9022% OFF
Rating: 4Rated 4 stars out of 5(32)

Deer Stags - Argos. Color Black/Blue. On sale for $55.00. MSRP $100.00. 45% 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: $55MSRP: $10045% 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)

Stacy Adams - Thompson Elastic Lace Inside Zip Boots. Color Brown. On sale for $104.62. MSRP $150.00. 30% off.

Brown Stacy Adams Thompson Elastic Lace Inside Zip Boots

Brown 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: Brown
Price: $104.62MSRP: $15030% OFF
Rating

Steve Madden - Montreaux. Color Black. On sale for $97.50. MSRP $130.00. 25% off.

Black Steve Madden Montreaux

Black Steve Madden Montreaux

Brand Name: Steve Madden
Product Name: Montreaux
Gender: Men's
Color: Black
Price: $97.50MSRP: $13025% OFF
Rating

Steve Madden - Hatton. Color Dark Grey. Low Stock. On sale for $135.35. MSRP $170.00. 20% off. 4.0 out of 5 stars

Low Stock

Gray Steve Madden Hatton

Gray Steve Madden Hatton

Brand Name: Steve Madden
Product Name: Hatton
Gender: Men's
Color: Dark Grey
Price: $135.35MSRP: $17020% OFF
Rating: 4Rated 4 stars out of 5(1)

Ariat - Midtown Rambler. Color Barn Brown. $169.95. 4.4 out of 5 stars

Brown Ariat Midtown Rambler

Brown Ariat Midtown Rambler

+2 colors/patterns

Brand Name: Ariat
Product Name: Midtown Rambler
Gender: Men's
Color: Barn Brown
Price: $169.95
Rating: 4Rated 4 stars out of 5(355)

Tommy Hilfiger - Berton. Color Black. Low Stock. On sale for $71.40. MSRP $119.00. 40% 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: $71.40MSRP: $11940% 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)

Johnston & Murphy - XC Flex Raleigh Chelsea. Color Tan Full Grain. Low Stock. On sale for $129.99. MSRP $185.00. 30% off. 4.4 out of 5 stars

Low Stock

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: $129.99MSRP: $18530% OFF
Rating: 4Rated 4 stars out of 5(69)

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(138)

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(302)

. Timberland PRO - Nashoba Composite Safety Toe. Color Black-2024 NEW. On sale for $164.95. MSRP $180.00. 8% 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: $164.95MSRP: $1808% OFF
Rating: 4Rated 4 stars out of 5(80)

Tommy Hilfiger - Vitus. Color Black. On sale for $59.50. MSRP $119.00. 50% off. 4.0 out of 5 stars

Black Tommy Hilfiger Vitus

Black Tommy Hilfiger Vitus

Brand Name: Tommy Hilfiger
Product Name: Vitus
Gender: Men's
Color: Black
Price: $59.50MSRP: $11950% OFF
Rating: 4Rated 4 stars out of 5(1)

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

L.L.Bean - Stonington Chelsea Boot Suede. Color Deepest Brown. On sale for $124.00. MSRP $139.00. 11% off. 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: $124MSRP: $13911% OFF
Rating: 4Rated 4 stars out of 5(5)

Caterpillar - Wheelbase Steel Toe. Color Clay Leather. $114.95. 3.0 out of 5 stars

Orange Caterpillar Wheelbase Steel Toe

Orange Caterpillar Wheelbase Steel Toe

Brand Name: Caterpillar
Product Name: Wheelbase Steel Toe
Gender: Men's
Color: Clay Leather
Price: $114.95
Rating: 3Rated 3 stars out of 5(1)

Eastland 1955 Edition - Daily Double. Color Brown Nubuck. Low Stock. On sale for $119.99. MSRP $125.00. 4% off. 3.4 out of 5 stars

Low Stock

Brown Eastland 1955 Edition Daily Double

Brown Eastland 1955 Edition Daily Double

+2

Brand Name: Eastland 1955 Edition
Product Name: Daily Double
Gender: Men's
Color: Brown Nubuck
Price: $119.99MSRP: $1254% OFF
Rating: 3Rated 3 stars out of 5(14)

Vans - Mte™ Standard Mid Chelsea Waterproof. Color Oatmeal/Brown. On sale for $135.00. MSRP $150.00. 10% off. 3.5 out of 5 stars

Neutral Vans Mte™ Standard Mid Chelsea Waterproof

Neutral Vans Mte™ Standard Mid Chelsea Waterproof

+3

Brand Name: Vans
Product Name: Mte™ Standard Mid Chelsea Waterproof
Gender: Unisex
Color: Oatmeal/Brown
Price: $135MSRP: $15010% OFF
Rating: 4Rated 4 stars out of 5(2)

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(305)

Florsheim - Lodge Plain Toe Gore Boots. Color Black Crazy Horse. $145.00. 4.4 out of 5 stars

Black Florsheim Lodge Plain Toe Gore Boots

Black Florsheim Lodge Plain Toe Gore Boots

+3

Brand Name: Florsheim
Product Name: Lodge Plain Toe Gore Boots
Gender: Men's
Color: Black Crazy Horse
Price: $145
Rating: 4Rated 4 stars out of 5(120)

SOREL - Cyprus Chelsea Waterproof. Color Khaki Ii/Jet. On sale for $93.75. MSRP $125.00. 25% off. 1.0 out of 5 stars

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: $93.75MSRP: $12525% OFF
Rating: 1Rated 1 star out of 5(1)

L.L.Bean - Bean Boot 6.5" Chelsea. Color Black/Warm Grey Opaque. $160.00. 3.1 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
Rating: 3Rated 3 stars out of 5(124)

Cole Haan - American Classics Chelsea Boots. Color Madeira Waterproof/Dark Java/Dark Java. On sale for $150.00. MSRP $200.00. 25% off.

Mahogany Cole Haan American Classics Chelsea Boots

Mahogany Cole Haan American Classics Chelsea Boots

+3

Brand Name: Cole Haan
Product Name: American Classics Chelsea Boots
Gender: Men's
Color: Madeira Waterproof/Dark Java/Dark Java
Price: $150MSRP: $20025% OFF
Rating

Frye - Tyler Flex Chelsea. Color Cognac. On sale for $174.20. MSRP $268.00. 35% off. 3.5 out of 5 stars

Tan Frye Tyler Flex Chelsea

Tan Frye Tyler Flex Chelsea

+4

Brand Name: Frye
Product Name: Tyler Flex Chelsea
Gender: Men's
Color: Cognac
Price: $174.20MSRP: $26835% OFF
Rating: 4Rated 4 stars out of 5(6)

Johnston & Murphy - XC+ Durham Chelsea Boots. Color Snuff Waterproof Waxed Suede. On sale for $198.95. MSRP $219.00. 9% off.

Brown Johnston & Murphy XC+ Durham Chelsea Boots

Brown Johnston & Murphy XC+ Durham Chelsea Boots

+2

Brand Name: Johnston & Murphy
Product Name: XC+ Durham Chelsea Boots
Gender: Men's
Color: Snuff Waterproof Waxed Suede
Price: $198.95MSRP: $2199% OFF
Rating

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)

Johnston & Murphy - Calder Chelsea Boots. Color Brown Oiled Full Grain. $178.95. 5.0 out of 5 stars

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: Brown Oiled Full Grain
Price: $178.95
Rating: 5Rated 5 stars out of 5(1)

Johnston & Murphy - Upton Chelsea Boots. Color Tan Full Grain. On sale for $161.10. MSRP $179.00. 10% off. 2.0 out of 5 stars

Tan Johnston & Murphy Upton Chelsea Boots

Tan Johnston & Murphy Upton Chelsea Boots

+2

Brand Name: Johnston & Murphy
Product Name: Upton Chelsea Boots
Gender: Men's
Color: Tan Full Grain
Price: $161.10MSRP: $17910% OFF
Rating: 2Rated 2 stars out of 5(1)

. 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)

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)

Steve Madden - Duke. Color Cognac Leather. $140.00. 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: $140
Rating: 5Rated 5 stars out of 5(1)

KEEN - KNX Chukka. Color Brindle/Plaza Taupe. Low Stock. On sale for $93.23. MSRP $159.95. 42% off. 3.8 out of 5 stars

Low Stock

Taupe KEEN KNX Chukka

Taupe KEEN KNX Chukka

+2

Brand Name: KEEN
Product Name: KNX Chukka
Gender: Men's
Color: Brindle/Plaza Taupe
Price: $93.23MSRP: $159.9542% OFF
Rating: 4Rated 4 stars out of 5(20)

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

Join Our Email List

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

*One code per email address.