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

Size 9.5 Stretch Leather Boots

55 items found

Sort By

Your Selections

Search Results

Timberland PRO - Nashoba Composite Safety Toe. Color Black-2024 NEW. $179.95. 4.1 out of 5 stars

Black Timberland PRO Nashoba Composite Safety Toe

Black Timberland PRO Nashoba Composite Safety Toe

Brand Name: Timberland PRO
Product Name: Nashoba Composite Safety Toe
Color: Black-2024 NEW
Price: $179.95
Rating: 4Rated 4 stars out of 5(47)

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

Brown Ariat Booker Ultra Square Toe Western Boots

Brown Ariat Booker Ultra Square Toe Western Boots

+4

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

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

Brown Marc Joseph New York Austin

Brown Marc Joseph New York Austin

+2

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

Carhartt - Millbrook 4" Romeo Soft Toe Wedge Boot. Color Black/Black. On sale for $108.74. MSRP $144.99.. 3.5 out of 5 stars

Black Carhartt Millbrook 4" Romeo Soft Toe Wedge Boot

Black Carhartt Millbrook 4" Romeo Soft Toe Wedge Boot

+1

Brand Name: Carhartt
Product Name: Millbrook 4" Romeo Soft Toe Wedge Boot
Color: Black/Black
Price: $108.74MSRP: $144.99
Rating: 3Rated 3 stars out of 5(22)

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

Black Born Hemlock

Black Born Hemlock

+2

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

Teva - Tusayan Chelsea. Color Chocolate Brown. Low Stock. $149.95. 4.3 out of 5 stars

9 left in stock

Brown Teva Tusayan Chelsea

Brown Teva Tusayan Chelsea

+2

Brand Name: Teva
Product Name: Tusayan Chelsea
Color: Chocolate Brown
Price: $149.95
Rating: 4Rated 4 stars out of 5(7)

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

Birkenstock - Highwood Deep Blue. Color Chocolate. $210.00. 4.0 out of 5 stars

Brown Birkenstock Highwood Deep Blue

Brown Birkenstock Highwood Deep Blue

Brand Name: Birkenstock
Product Name: Highwood Deep Blue
Color: Chocolate
Price: $210.00
Rating: 4Rated 4 stars out of 5(1)

Polo Ralph Lauren - Oslo Chelsea. Color Light Beige. On sale for $107.71. 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: $107.71MSRP: $178.00
Rating: 3Rated 3 stars out of 5(1)

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

8 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

Zamberlan - 226 Salathe' Trek GTX® RR. Color Black/Grey. Low Stock. $330.00.

6 left in stock

Black Zamberlan 226 Salathe' Trek GTX® RR

Black Zamberlan 226 Salathe' Trek GTX® RR

Brand Name: Zamberlan
Product Name: 226 Salathe' Trek GTX® RR
Color: Black/Grey
Price: $330.00
Rating

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)

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)

Johnston & Murphy - Kelton Chelsea. Color Black Full Grain. Low Stock. On sale for $108.61. MSRP $155.00.. 3.0 out of 5 stars

4 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: $108.61MSRP: $155.00
Rating: 3Rated 3 stars out of 5(1)

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)

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

Merrell - Moab 3 Mid Waterproof. Color Avocado. $144.95. 4.5 out of 5 stars

Green Merrell Moab 3 Mid Waterproof

Green Merrell Moab 3 Mid Waterproof

+3

Brand Name: Merrell
Product Name: Moab 3 Mid Waterproof
Color: Avocado
Price: $144.95
Rating: 4Rated 4 stars out of 5(448)

Carhartt - Millbrook 4" Romeo Steel Toe Wedge Work Boot. Color Brown Oil Tanned. On sale for $112.49. MSRP $149.99.. 3.3 out of 5 stars

Brown Carhartt Millbrook 4" Romeo Steel Toe Wedge Work Boot

Brown Carhartt Millbrook 4" Romeo Steel Toe Wedge Work Boot

Brand Name: Carhartt
Product Name: Millbrook 4" Romeo Steel Toe Wedge Work Boot
Color: Brown Oil Tanned
Price: $112.49MSRP: $149.99
Rating: 3Rated 3 stars out of 5(3)

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)

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)

Allen Edmonds - Liverpool. Color Chili. Low Stock. $495.00. 4.3 out of 5 stars

7 left in stock

Brown Allen Edmonds Liverpool

Brown Allen Edmonds Liverpool

+3

Brand Name: Allen Edmonds
Product Name: Liverpool
Color: Chili
Price: $495.00
Rating: 4Rated 4 stars out of 5(145)

Georgia Boot - 6" Flxpoint Ultra Comp Toe Chelsea. Color Brown. On sale for $162.00. MSRP $172.00.. 3.0 out of 5 stars

Brown Georgia Boot 6" Flxpoint Ultra Comp Toe Chelsea

Brown Georgia Boot 6" Flxpoint Ultra Comp Toe Chelsea

Brand Name: Georgia Boot
Product Name: 6" Flxpoint Ultra Comp Toe Chelsea
Color: Brown
Price: $162.00MSRP: $172.00
Rating: 3Rated 3 stars out of 5(2)

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

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

Brown Johnston & Murphy Upton Chelsea

Brown Johnston & Murphy Upton Chelsea

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

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)

Wolverine - Floorhand Waterproof Romeo. Color Dark Brown. Low Stock. On sale for $99.95. MSRP $110.00.. 3.5 out of 5 stars

9 left in stock

Brown Wolverine Floorhand Waterproof Romeo

Brown Wolverine Floorhand Waterproof Romeo

Brand Name: Wolverine
Product Name: Floorhand Waterproof Romeo
Color: Dark Brown
Price: $99.95MSRP: $110.00
Rating: 4Rated 4 stars out of 5(4)

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

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)

. 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

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)

Thomas & Vine - Jaylon. Color Black. Low Stock. On sale for $94.07. MSRP $169.99.. 3.0 out of 5 stars

9 left in stock

Black Thomas & Vine Jaylon

Black Thomas & Vine Jaylon

Brand Name: Thomas & Vine
Product Name: Jaylon
Color: Black
Price: $94.07MSRP: $169.99
Rating: 3Rated 3 stars out of 5(1)

KEEN - Revel IV Chelsea. Color Canteen/Black. Low Stock. On sale for $109.99. MSRP $170.00.. 3.2 out of 5 stars

8 left in stock

Olive KEEN Revel IV Chelsea

Olive KEEN Revel IV Chelsea

+2

Brand Name: KEEN
Product Name: Revel IV Chelsea
Color: Canteen/Black
Price: $109.99MSRP: $170.00
Rating: 3Rated 3 stars out of 5(6)

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)

Irish Setter - Two Harbors 11" Waterproof Soft-Toe Pull-On EH. Color Brown. On sale for $214.95. MSRP $239.99..

Brown Irish Setter Two Harbors 11" Waterproof Soft-Toe Pull-On EH

Brown Irish Setter Two Harbors 11" Waterproof Soft-Toe Pull-On EH

Brand Name: Irish Setter
Product Name: Two Harbors 11" Waterproof Soft-Toe Pull-On EH
Color: Brown
Price: $214.95MSRP: $239.99
Rating

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)

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)

Carhartt - Force 4" Romeo Soft Toe. Color Dark Bison Oil Tanned. On sale for $104.99. MSRP $139.99.. 2.6 out of 5 stars

Brown Carhartt Force 4" Romeo Soft Toe

Brown Carhartt Force 4" Romeo Soft Toe

Brand Name: Carhartt
Product Name: Force 4" Romeo Soft Toe
Color: Dark Bison Oil Tanned
Price: $104.99MSRP: $139.99
Rating: 3Rated 3 stars out of 5(8)

DeWALT - Flex Albany. Color Nature Pitstop. On sale for $109.95. MSRP $119.99.. 4.7 out of 5 stars

Brown DeWALT Flex Albany

Brown DeWALT Flex Albany

Brand Name: DeWALT
Product Name: Flex Albany
Color: Nature Pitstop
Price: $109.95MSRP: $119.99
Rating: 5Rated 5 stars out of 5(13)

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)

Carhartt - Wedge 5" Chelsea Pull-On Boot Steel Toe. Color Dark Bison Oil Tanned. $154.99. 3.0 out of 5 stars

Brown Carhartt Wedge 5" Chelsea Pull-On Boot Steel Toe

Brown Carhartt Wedge 5" Chelsea Pull-On Boot Steel Toe

Brand Name: Carhartt
Product Name: Wedge 5" Chelsea Pull-On Boot Steel Toe
Color: Dark Bison Oil Tanned
Price: $154.99
Rating: 3Rated 3 stars out of 5(3)

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

6 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)

KEEN Utility - Seattle Romeo (Soft Toe). Color Cascade Brown/Black. $144.95. 3.7 out of 5 stars

Brown KEEN Utility Seattle Romeo (Soft Toe)

Brown KEEN Utility Seattle Romeo (Soft Toe)

Brand Name: KEEN Utility
Product Name: Seattle Romeo (Soft Toe)
Color: Cascade Brown/Black
Price: $144.95
Rating: 4Rated 4 stars out of 5(17)

Florsheim - Lodge Plain Toe Gore Boot. Color Black Crazy Horse. $129.95. 4.6 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
Color: Black Crazy Horse
Price: $129.95
Rating: 5Rated 5 stars out of 5(96)

Georgia Boot - Wedge Waterproof Chelsea Work Boot. Color Dark Brown. On sale for $160.00. MSRP $182.00.. 4.4 out of 5 stars

Brown Georgia Boot Wedge Waterproof Chelsea Work Boot

Brown Georgia Boot Wedge Waterproof Chelsea Work Boot

Brand Name: Georgia Boot
Product Name: Wedge Waterproof Chelsea Work Boot
Color: Dark Brown
Price: $160.00MSRP: $182.00
Rating: 4Rated 4 stars out of 5(23)

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

Georgia Boot - Eagle One Waterproof Chelsea Soft Toe. Color Brown. On sale for $155.00. MSRP $165.00.. 4.1 out of 5 stars

Brown Georgia Boot Eagle One Waterproof Chelsea Soft Toe

Brown Georgia Boot Eagle One Waterproof Chelsea Soft Toe

Brand Name: Georgia Boot
Product Name: Eagle One Waterproof Chelsea Soft Toe
Color: Brown
Price: $155.00MSRP: $165.00
Rating: 4Rated 4 stars out of 5(48)

Georgia Boot - Giant ReVamp Romeo Soft Toe. Color Brown. On sale for $123.00. MSRP $133.00.. 4.3 out of 5 stars

Brown Georgia Boot Giant ReVamp Romeo Soft Toe

Brown Georgia Boot Giant ReVamp Romeo Soft Toe

Brand Name: Georgia Boot
Product Name: Giant ReVamp Romeo Soft Toe
Color: Brown
Price: $123.00MSRP: $133.00
Rating: 4Rated 4 stars out of 5(30)

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

Black Deer Stags Argos

Black Deer Stags Argos

+2

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

Ariat - Groundbreaker Chelsea H2O Steel Toe. Color Dark Brown. $169.95. 4.4 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
Color: Dark Brown
Price: $169.95
Rating: 4Rated 4 stars out of 5(100)

Ariat - Wexford H2O. Color Java. $199.95. 4.6 out of 5 stars

Brown Ariat Wexford H2O

Brown Ariat Wexford H2O

Brand Name: Ariat
Product Name: Wexford H2O
Color: Java
Price: $199.95
Rating: 5Rated 5 stars out of 5(190)

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)

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)

KEEN - Anchorage Boot III Waterproof. Color Dark Earth/Mulch. On sale for $128.00. MSRP $160.00.. 4.1 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
Color: Dark Earth/Mulch
Price: $128.00MSRP: $160.00
Rating: 4Rated 4 stars out of 5(152)

Georgia Boot - Romeo Wedge. Color Soggy Brown. On sale for $104.00. MSRP $114.00.. 4.5 out of 5 stars

Brown Georgia Boot Romeo Wedge

Brown Georgia Boot Romeo Wedge

Brand Name: Georgia Boot
Product Name: Romeo Wedge
Color: Soggy Brown
Price: $104.00MSRP: $114.00
Rating: 4Rated 4 stars out of 5(362)

Georgia Boot - Georgia Giant Romeo Steel Toe. Color Soggy Brown. Low Stock. On sale for $110.00. MSRP $120.00.. 4.3 out of 5 stars

1 left in stock

Brown Georgia Boot Georgia Giant Romeo Steel Toe

Brown Georgia Boot Georgia Giant Romeo Steel Toe

Brand Name: Georgia Boot
Product Name: Georgia Giant Romeo Steel Toe
Color: Soggy Brown
Price: $110.00MSRP: $120.00
Rating: 4Rated 4 stars out of 5(74)

Get on the List

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