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

Size 9.5 Leather Chelsea Boots

62 items found

Sort By

Your Selections

Search Results

Marc Joseph New York - Austin. Color Black Washed Grainy. Low Stock. On sale for $89.95. MSRP $195.00.. 5.0 out of 5 stars

7 left in stock

Black Marc Joseph New York Austin

Black Marc Joseph New York Austin

+2

Brand Name: Marc Joseph New York
Product Name: Austin
Color: Black Washed Grainy
Price: $89.95MSRP: $195.00
Rating: 5Rated 5 stars out of 5(5)

Steve Madden - Duke. Color Cognac Leather. $139.96. 5.0 out of 5 stars

Brown Steve Madden Duke

Brown Steve Madden Duke

Brand Name: Steve Madden
Product Name: Duke
Color: Cognac Leather
Price: $139.96
Rating: 5Rated 5 stars out of 5(1)

Florsheim - Lodge Plain Toe Gore Boot. Color Chestnut Smooth. $129.95. 4.6 out of 5 stars

Brown Florsheim Lodge Plain Toe Gore Boot

Brown Florsheim Lodge Plain Toe Gore Boot

+3

Brand Name: Florsheim
Product Name: Lodge Plain Toe Gore Boot
Color: Chestnut Smooth
Price: $129.95
Rating: 5Rated 5 stars out of 5(95)

Ariat - Wexford Waterproof. Color Dark Brown. $199.95. 4.7 out of 5 stars

Brown Ariat Wexford Waterproof

Brown Ariat Wexford Waterproof

+2

Brand Name: Ariat
Product Name: Wexford Waterproof
Color: Dark Brown
Price: $199.95
Rating: 5Rated 5 stars out of 5(182)

Ariat - Booker Ultra Square Toe Western Boots. Color Black Deertan. $149.95. 4.7 out of 5 stars

Black Ariat Booker Ultra Square Toe Western Boots

Black Ariat Booker Ultra Square Toe Western Boots

+4

Brand Name: Ariat
Product Name: Booker Ultra Square Toe Western Boots
Color: Black Deertan
Price: $149.95
Rating: 5Rated 5 stars out of 5(42)

Florsheim - Duke. Color Black Cavello. $149.95. 4.5 out of 5 stars

Black Florsheim Duke

Black Florsheim Duke

+2

Brand Name: Florsheim
Product Name: Duke
Color: Black Cavello
Price: $149.95
Rating: 5Rated 5 stars out of 5(898)

Red Wing Heritage - Classic Chelsea. Color Black Harness. $329.99. 4.8 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
Color: Black Harness
Price: $329.99
Rating: 5Rated 5 stars out of 5(10)

Marc Joseph New York - Crosby Boots. Color Cognac Grainy. On sale for $85.07. MSRP $195.00.. 5.0 out of 5 stars

Brown Marc Joseph New York Crosby Boots

Brown Marc Joseph New York Crosby Boots

Brand Name: Marc Joseph New York
Product Name: Crosby Boots
Color: Cognac Grainy
Price: $85.07MSRP: $195.00
Rating: 5Rated 5 stars out of 5(1)

Born - Brody. Color Taupe Dist. $140.00. 4.7 out of 5 stars

Taupe Born Brody

Taupe Born Brody

+3

Brand Name: Born
Product Name: Brody
Color: Taupe Dist
Price: $140.00
Rating: 5Rated 5 stars out of 5(23)

Ariat - Booker Ultra Western Boots. Color Charro Tan. $149.95. 4.7 out of 5 stars

Brown Ariat Booker Ultra Western Boots

Brown Ariat Booker Ultra Western Boots

Brand Name: Ariat
Product Name: Booker Ultra Western Boots
Color: Charro Tan
Price: $149.95
Rating: 5Rated 5 stars out of 5(178)

Stacy Adams - Kalen Chelsea Boot. Color Cognac. On sale for $104.00. MSRP $130.00.. 4.8 out of 5 stars

Tan Stacy Adams Kalen Chelsea Boot

Tan Stacy Adams Kalen Chelsea Boot

+2

Brand Name: Stacy Adams
Product Name: Kalen Chelsea Boot
Color: Cognac
Price: $104.00MSRP: $130.00
Rating: 5Rated 5 stars out of 5(12)

Florsheim - Rucci Plain Toe Gore Boot. Color Black. $139.95. 4.8 out of 5 stars

Black Florsheim Rucci Plain Toe Gore Boot

Black Florsheim Rucci Plain Toe Gore Boot

+2

Brand Name: Florsheim
Product Name: Rucci Plain Toe Gore Boot
Color: Black
Price: $139.95
Rating: 5Rated 5 stars out of 5(25)

Johnston & Murphy - Upton Chelsea. Color Tan Full Grain. $169.00. 4.8 out of 5 stars

Tan Johnston & Murphy Upton Chelsea

Tan Johnston & Murphy Upton Chelsea

Brand Name: Johnston & Murphy
Product Name: Upton Chelsea
Color: Tan Full Grain
Price: $169.00
Rating: 5Rated 5 stars out of 5(82)

ECCO - Grainer Chelsea Boot. Color Black. On sale for $132.87. MSRP $190.00.. 4.8 out of 5 stars

Black ECCO Grainer Chelsea Boot

Black ECCO Grainer Chelsea Boot

Brand Name: ECCO
Product Name: Grainer Chelsea Boot
Color: Black
Price: $132.87MSRP: $190.00
Rating: 5Rated 5 stars out of 5(4)

BOSS - Colby Chelsea Boot. Color Medium Beige. On sale for $137.31. MSRP $199.00.. 5.0 out of 5 stars

Beige BOSS Colby Chelsea Boot

Beige BOSS Colby Chelsea Boot

+2

Brand Name: BOSS
Product Name: Colby Chelsea Boot
Color: Medium Beige
Price: $137.31MSRP: $199.00
Rating: 5Rated 5 stars out of 5(1)

Johnston & Murphy - XC Flex Raleigh Chelsea. Color Black Full Grain. $185.00. 4.5 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
Color: Black Full Grain
Price: $185.00
Rating: 5Rated 5 stars out of 5(50)

Allen Edmonds - Dawson. Color Mahogany. On sale for $380.00. MSRP $475.00.. 4.6 out of 5 stars

Mahogany Allen Edmonds Dawson

Mahogany Allen Edmonds Dawson

Brand Name: Allen Edmonds
Product Name: Dawson
Color: Mahogany
Price: $380.00MSRP: $475.00
Rating: 5Rated 5 stars out of 5(14)

UGG - Burleigh Chelsea. Color Chestnut. $169.95. 4.5 out of 5 stars

Brown UGG Burleigh Chelsea

Brown UGG Burleigh Chelsea

+3

Brand Name: UGG
Product Name: Burleigh Chelsea
Color: Chestnut
Price: $169.95
Rating: 5Rated 5 stars out of 5(16)

Bogs - Classic Casual Chelsea II. Color Brown. $149.95. 4.9 out of 5 stars

Brown Bogs Classic Casual Chelsea II

Brown Bogs Classic Casual Chelsea II

+2

Brand Name: Bogs
Product Name: Classic Casual Chelsea II
Color: Brown
Price: $149.95
Rating: 5Rated 5 stars out of 5(7)

Ariat - Hybrid Low Western Boot. Color Stone. $159.95. 4.6 out of 5 stars

White Ariat Hybrid Low Western Boot

White Ariat Hybrid Low Western Boot

Brand Name: Ariat
Product Name: Hybrid Low Western Boot
Color: Stone
Price: $159.95
Rating: 5Rated 5 stars out of 5(64)

Ariat - Midtown Rambler Boots. Color Matte Black. $159.95. 5.0 out of 5 stars

Black Ariat Midtown Rambler Boots

Black Ariat Midtown Rambler Boots

Brand Name: Ariat
Product Name: Midtown Rambler Boots
Color: Matte Black
Price: $159.95
Rating: 5Rated 5 stars out of 5(7)

Ariat - Sport Booker Ultra. Color Distressed Tan. $149.95. 4.8 out of 5 stars

Tan Ariat Sport Booker Ultra

Tan Ariat Sport Booker Ultra

Brand Name: Ariat
Product Name: Sport Booker Ultra
Color: Distressed Tan
Price: $149.95
Rating: 5Rated 5 stars out of 5(453)

Cole Haan - Hawthorne Chelsea Boot. Color Dark Chocolate. $140.00. 5.0 out of 5 stars

Brown Cole Haan Hawthorne Chelsea Boot

Brown Cole Haan Hawthorne Chelsea Boot

+1

Brand Name: Cole Haan
Product Name: Hawthorne Chelsea Boot
Color: Dark Chocolate
Price: $140.00
Rating: 5Rated 5 stars out of 5(2)

Ariat - Midtown Rambler. Color Barn Brown. $159.95. 4.4 out of 5 stars

Brown Ariat Midtown Rambler

Brown Ariat Midtown Rambler

+2 colors/patterns

Brand Name: Ariat
Product Name: Midtown Rambler
Color: Barn Brown
Price: $159.95
Rating: 4Rated 4 stars out of 5(252)

Deer Stags - Argos. Color Tan/Blue. On sale for $54.99. MSRP $100.00.. 3.7 out of 5 stars

Tan Deer Stags Argos

Tan Deer Stags Argos

+2

Brand Name: Deer Stags
Product Name: Argos
Color: Tan/Blue
Price: $54.99MSRP: $100.00
Rating: 4Rated 4 stars out of 5(24)

Blundstone - Lug Boot. Color Rustic Black. $234.95. 4.5 out of 5 stars

Black Blundstone Lug Boot

Black Blundstone Lug Boot

+1

Brand Name: Blundstone
Product Name: Lug Boot
Color: Rustic Black
Price: $234.95
Rating: 4Rated 4 stars out of 5(17)

Born - Hemlock. Color Brown Full Grain. $135.00. 4.3 out of 5 stars

Brown Born Hemlock

Brown Born Hemlock

+2

Brand Name: Born
Product Name: Hemlock
Color: Brown Full Grain
Price: $135.00
Rating: 4Rated 4 stars out of 5(189)

Florsheim - Renegade Plain Toe Gore Boot. Color Brown Crazy Horse. $149.95. 4.4 out of 5 stars

Brown Florsheim Renegade Plain Toe Gore Boot

Brown Florsheim Renegade Plain Toe Gore Boot

+3

Brand Name: Florsheim
Product Name: Renegade Plain Toe Gore Boot
Color: Brown Crazy Horse
Price: $149.95
Rating: 4Rated 4 stars out of 5(19)

Birkenstock - Stalon - Nubuck Leather (Unisex). Color Black Nubuck. $200.00. 3.8 out of 5 stars

Black Birkenstock Stalon - Nubuck Leather (Unisex)

Black Birkenstock Stalon - Nubuck Leather (Unisex)

Brand Name: Birkenstock
Product Name: Stalon - Nubuck Leather (Unisex)
Color: Black Nubuck
Price: $200.00
Rating: 4Rated 4 stars out of 5(42)

Dansko - Frankie. Color Black Oiled. $159.95. 4.2 out of 5 stars

Black Dansko Frankie

Black Dansko Frankie

+2

Brand Name: Dansko
Product Name: Frankie
Color: Black Oiled
Price: $159.95
Rating: 4Rated 4 stars out of 5(278)

Allen Edmonds - Liverpool. Color Walnut. $495.00. 4.2 out of 5 stars

Brown Allen Edmonds Liverpool

Brown Allen Edmonds Liverpool

+3

Brand Name: Allen Edmonds
Product Name: Liverpool
Color: Walnut
Price: $495.00
Rating: 4Rated 4 stars out of 5(89)

Nunn Bush - 1912 Plain Toe Chelsea Boot. Color Black. On sale for $84.95. MSRP $115.00.. 3.6 out of 5 stars

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
Color: Black
Price: $84.95MSRP: $115.00
Rating: 4Rated 4 stars out of 5(8)

Red Wing Heritage - Weekend Chelsea. Color Copper Rough & Tough Leather. $259.99. 4.1 out of 5 stars

Brown Red Wing Heritage Weekend Chelsea

Brown Red Wing Heritage Weekend Chelsea

Brand Name: Red Wing Heritage
Product Name: Weekend Chelsea
Color: Copper Rough & Tough Leather
Price: $259.99
Rating: 4Rated 4 stars out of 5(21)

Chaco - Fields Chelsea Waterproof. Color Black. On sale for $116.99. MSRP $160.00.. 4.1 out of 5 stars

Black Chaco Fields Chelsea Waterproof

Black Chaco Fields Chelsea Waterproof

Brand Name: Chaco
Product Name: Fields Chelsea Waterproof
Color: Black
Price: $116.99MSRP: $160.00
Rating: 4Rated 4 stars out of 5(23)

Johnston & Murphy - Barrett Chelsea. Color Mahogany Full Grain. Low Stock. $185.00. 4.3 out of 5 stars

9 left in stock

Brown Johnston & Murphy Barrett Chelsea

Brown Johnston & Murphy Barrett Chelsea

+2

Brand Name: Johnston & Murphy
Product Name: Barrett Chelsea
Color: Mahogany Full Grain
Price: $185.00
Rating: 4Rated 4 stars out of 5(131)

Nunn Bush - Otis Plain Toe Chelsea Boot with KORE Walking Comfort Technology. Color Black Tumbled. On sale for $84.95. MSRP $115.00.. 4.2 out of 5 stars

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

Black 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
Color: Black Tumbled
Price: $84.95MSRP: $115.00
Rating: 4Rated 4 stars out of 5(95)

Columbia - Landroamer™ Scout. Color Espresso II/Warp Red. $119.95. 4.3 out of 5 stars

Tan Columbia Landroamer™ Scout

Tan Columbia Landroamer™ Scout

+2

Brand Name: Columbia
Product Name: Landroamer™ Scout
Color: Espresso II/Warp Red
Price: $119.95
Rating: 4Rated 4 stars out of 5(20)

Frye - Bowery Chelsea. Color Cognac Antique Pull Up. Low Stock. $327.95. 3.9 out of 5 stars

8 left in stock

Brown Frye Bowery Chelsea

Brown Frye Bowery Chelsea

Brand Name: Frye
Product Name: Bowery Chelsea
Color: Cognac Antique Pull Up
Price: $327.95
Rating: 4Rated 4 stars out of 5(15)

Cole Haan - Washington Grand Laser Chelsea Boot. Color British Tan/Dark Chocolate. On sale for $231.42. MSRP $406.00.. 4.4 out of 5 stars

Brown Cole Haan Washington Grand Laser Chelsea Boot

Brown Cole Haan Washington Grand Laser Chelsea Boot

Brand Name: Cole Haan
Product Name: Washington Grand Laser Chelsea Boot
Color: British Tan/Dark Chocolate
Price: $231.42MSRP: $406.00
Rating: 4Rated 4 stars out of 5(12)

Blundstone - BL2391 Ankle Boots. Color Brown Suede. Low Stock. $254.95. 3.0 out of 5 stars

7 left in stock

Brown Blundstone BL2391 Ankle Boots

Brown Blundstone BL2391 Ankle Boots

Brand Name: Blundstone
Product Name: BL2391 Ankle Boots
Color: Brown Suede
Price: $254.95
Rating: 3Rated 3 stars out of 5(1)

Deer Stags - Brayden. Color Brown. On sale for $62.29. MSRP $100.00.. 3.0 out of 5 stars

Brown Deer Stags Brayden

Brown Deer Stags Brayden

+2

Brand Name: Deer Stags
Product Name: Brayden
Color: Brown
Price: $62.29MSRP: $100.00
Rating: 3Rated 3 stars out of 5(1)

Thomas & Vine - Jaylon. Color Black. Low Stock. On sale for $93.93. MSRP $169.99.. 3.0 out of 5 stars

8 left in stock

Black Thomas & Vine Jaylon

Black Thomas & Vine Jaylon

Brand Name: Thomas & Vine
Product Name: Jaylon
Color: Black
Price: $93.93MSRP: $169.99
Rating: 3Rated 3 stars out of 5(1)

Steve Madden - Sverne. Color Tan Leather. On sale for $134.87. MSRP $150.00.. 3.0 out of 5 stars

Tan Steve Madden Sverne

Tan Steve Madden Sverne

Brand Name: Steve Madden
Product Name: Sverne
Color: Tan Leather
Price: $134.87MSRP: $150.00
Rating: 3Rated 3 stars out of 5(1)

Johnston & Murphy - Kelton Chelsea. Color Black Full Grain. Low Stock. On sale for $114.70. MSRP $155.00.. 3.0 out of 5 stars

7 left in stock

Black Johnston & Murphy Kelton Chelsea

Black Johnston & Murphy Kelton Chelsea

Brand Name: Johnston & Murphy
Product Name: Kelton Chelsea
Color: Black Full Grain
Price: $114.70MSRP: $155.00
Rating: 3Rated 3 stars out of 5(1)

ECCO - Helsinki 2 Chelsea Boot. Color Potting Soil. $190.00. 3.0 out of 5 stars

Brown ECCO Helsinki 2 Chelsea Boot

Brown ECCO Helsinki 2 Chelsea Boot

+2

Brand Name: ECCO
Product Name: Helsinki 2 Chelsea Boot
Color: Potting Soil
Price: $190.00
Rating: 3Rated 3 stars out of 5(4)

Clarks - Morris Easy. Color Black Leather. On sale for $88.22. MSRP $130.00.. 3.0 out of 5 stars

Black Clarks Morris Easy

Black Clarks Morris Easy

Brand Name: Clarks
Product Name: Morris Easy
Color: Black Leather
Price: $88.22MSRP: $130.00
Rating: 3Rated 3 stars out of 5(4)

Polo Ralph Lauren - Oslo Chelsea. Color Light Beige. On sale for $136.06. MSRP $178.00.. 3.0 out of 5 stars

Beige Polo Ralph Lauren Oslo Chelsea

Beige Polo Ralph Lauren Oslo Chelsea

+2 colors/patterns

Brand Name: Polo Ralph Lauren
Product Name: Oslo Chelsea
Color: Light Beige
Price: $136.06MSRP: $178.00
Rating: 3Rated 3 stars out of 5(1)

To Boot New York - Shelby II. Color Dark Brown Leather. Low Stock. On sale for $191.52. MSRP $399.00.. 2.0 out of 5 stars

3 left in stock

Brown To Boot New York Shelby II

Brown To Boot New York Shelby II

+2 colors/patterns

Brand Name: To Boot New York
Product Name: Shelby II
Color: Dark Brown Leather
Price: $191.52MSRP: $399.00
Rating: 2Rated 2 stars out of 5(1)

COACH - Dalton Chelsea Boot. Color Black. $295.00. 1.0 out of 5 stars

Black COACH Dalton Chelsea Boot

Black COACH Dalton Chelsea Boot

+2

Brand Name: COACH
Product Name: Dalton Chelsea Boot
Color: Black
Price: $295.00
Rating: 1Rated 1 star out of 5(1)

Nisolo - Marco Everyday Chelsea Boot. Color Brown. $259.99.

Brown Nisolo Marco Everyday Chelsea Boot

Brown Nisolo Marco Everyday Chelsea Boot

+3

Brand Name: Nisolo
Product Name: Marco Everyday Chelsea Boot
Color: Brown
Price: $259.99
Rating

. Nisolo - All-Weather Chelsea Boot. Color Dark Tobacco. $260.00.

Red Nisolo All-Weather Chelsea Boot

Red Nisolo All-Weather Chelsea Boot

Brand Name: Nisolo
Product Name: All-Weather Chelsea Boot
Color: Dark Tobacco
Price: $260.00
Rating

Twisted X - MHKB003. Color Distressed Saddle/Saddle. $159.95.

Brown Twisted X MHKB003

Brown Twisted X MHKB003

Brand Name: Twisted X
Product Name: MHKB003
Color: Distressed Saddle/Saddle
Price: $159.95
Rating

Mephisto - Murray. Color Dark Brown Leather. Low Stock. $498.95.

7 left in stock

Brown Mephisto Murray

Brown Mephisto Murray

+2

Brand Name: Mephisto
Product Name: Murray
Color: Dark Brown Leather
Price: $498.95
Rating

Vince Camuto - Huntsley. Color Honey 2. Low Stock. $169.00.

9 left in stock

Tan Vince Camuto Huntsley

Tan Vince Camuto Huntsley

Brand Name: Vince Camuto
Product Name: Huntsley
Color: Honey 2
Price: $169.00
Rating

Milwaukee Boot Company - Shorewood Chelsea Boot. Color Black. Low Stock. $209.00.

2 left in stock

Black Milwaukee Boot Company Shorewood Chelsea Boot

Black Milwaukee Boot Company Shorewood Chelsea Boot

Brand Name: Milwaukee Boot Company
Product Name: Shorewood Chelsea Boot
Color: Black
Price: $209.00
Rating

Twisted X - MCA0013. Color Oiled Saddle. $159.95.

Tan Twisted X MCA0013

Tan Twisted X MCA0013

Brand Name: Twisted X
Product Name: MCA0013
Color: Oiled Saddle
Price: $159.95
Rating

COACH - Carver Boot. Color Black. On sale for $265.16. MSRP $295.00..

Black COACH Carver Boot

Black COACH Carver Boot

Brand Name: COACH
Product Name: Carver Boot
Color: Black
Price: $265.16MSRP: $295.00
Rating

SeaVees - Ballard Boot. Color Stone. On sale for $103.60. MSRP $110.00..

White SeaVees Ballard Boot

White SeaVees Ballard Boot

Brand Name: SeaVees
Product Name: Ballard Boot
Color: Stone
Price: $103.60MSRP: $110.00
Rating

La Canadienne - Luther. Color Biscotti Suede. $475.00.

Gold La Canadienne Luther

Gold La Canadienne Luther

Brand Name: La Canadienne
Product Name: Luther
Color: Biscotti Suede
Price: $475.00
Rating

Forsake - Phil Chelsea. Color Black. Low Stock. $145.00.

9 left in stock

Black Forsake Phil Chelsea

Black Forsake Phil Chelsea

+2

Brand Name: Forsake
Product Name: Phil Chelsea
Color: Black
Price: $145.00
Rating

Dockers - Novato. Color Dark Brown. On sale for $69.99. MSRP $95.00..

Brown Dockers Novato

Brown Dockers Novato

Brand Name: Dockers
Product Name: Novato
Color: Dark Brown
Price: $69.99MSRP: $95.00
Rating

Marc Joseph New York - Crosby ST. Color Black Soft Grainy. On sale for $99.95. MSRP $195.00..

Black Marc Joseph New York Crosby ST

Black Marc Joseph New York Crosby ST

Brand Name: Marc Joseph New York
Product Name: Crosby ST
Color: Black Soft Grainy
Price: $99.95MSRP: $195.00
Rating

Get on the List

Subscribe to Zappos emails for exclusive product launches, early notifications for sales, and a few extra-special surprises.