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Size 8.5 Ankle Leather Shoes

143 items found

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Vince - Jerome. Color Cocoa Brown Leather. On sale for $300.00. MSRP $330.00. 9% off.

Brown Vince Jerome

Brown Vince Jerome

Brand Name: Vince
Product Name: Jerome
Gender: Men's
Color: Cocoa Brown Leather
Price: $300MSRP: $3309% OFF
Rating

Johnston & Murphy - Latham Plain Toe Shearling Boots. Color Dark Brown European Calfskin/Shearling. On sale for $313.20. MSRP $348.00. 10% off.

Brown Johnston & Murphy Latham Plain Toe Shearling Boots

Brown Johnston & Murphy Latham Plain Toe Shearling Boots

Brand Name: Johnston & Murphy
Product Name: Latham Plain Toe Shearling Boots
Gender: Men's
Color: Dark Brown European Calfskin/Shearling
Price: $313.20MSRP: $34810% OFF
Rating

Asolo - Greenwood EVO GV. Color Graphite 1. Low Stock. $370.00.

Low Stock

Gray Asolo Greenwood EVO GV

Gray Asolo Greenwood EVO GV

Brand Name: Asolo
Product Name: Greenwood EVO GV
Gender: Men's
Color: Graphite 1
Price: $370
Rating

KEEN Utility - Coburg 8" Waterproof (Steel Toe). Color Cascade Brown/Brindle. $215.00. 4.0 out of 5 stars

Brown KEEN Utility Coburg 8" Waterproof (Steel Toe)

Brown KEEN Utility Coburg 8" Waterproof (Steel Toe)

Brand Name: KEEN Utility
Product Name: Coburg 8" Waterproof (Steel Toe)
Gender: Men's
Color: Cascade Brown/Brindle
Price: $215
Rating: 4Rated 4 stars out of 5(76)

To Boot New York - Gilmour. Color Black. Low Stock. $525.00.

Low Stock

Black To Boot New York Gilmour

Black To Boot New York Gilmour

Brand Name: To Boot New York
Product Name: Gilmour
Gender: Men's
Color: Black
Price: $525
Rating

Taft - Boston. Color Olive. $295.00.

Olive Taft Boston

Olive Taft Boston

+3

Brand Name: Taft
Product Name: Boston
Gender: Men's
Color: Olive
Price: $295
Rating

KEEN Utility - Snapline RF Waterproof Boot (Carbon-Fiber Toe). Color Vintage Indigo/Black. $230.00. 4.5 out of 5 stars

Blue KEEN Utility Snapline RF Waterproof Boot (Carbon-Fiber Toe)

Blue KEEN Utility Snapline RF Waterproof Boot (Carbon-Fiber Toe)

Brand Name: KEEN Utility
Product Name: Snapline RF Waterproof Boot (Carbon-Fiber Toe)
Gender: Men's
Color: Vintage Indigo/Black
Price: $230
Rating: 5Rated 5 stars out of 5(2)

Allen Edmonds - Higgins Mill Lace-Up. Color Brown Waxed Suede. On sale for $385.00. MSRP $550.00. 30% off.

Brown Allen Edmonds Higgins Mill Lace-Up

Brown Allen Edmonds Higgins Mill Lace-Up

Brand Name: Allen Edmonds
Product Name: Higgins Mill Lace-Up
Gender: Men's
Color: Brown Waxed Suede
Price: $385MSRP: $55030% OFF
Rating

Taft - Darcey. Color Brown. $295.00.

Brown Taft Darcey

Brown Taft Darcey

Brand Name: Taft
Product Name: Darcey
Gender: Men's
Color: Brown
Price: $295
Rating

Asolo - Power Matic 200 GV. Color Graphite. $450.00. 4.8 out of 5 stars

Gray Asolo Power Matic 200 GV

Gray Asolo Power Matic 200 GV

Brand Name: Asolo
Product Name: Power Matic 200 GV
Gender: Men's
Color: Graphite
Price: $450
Rating: 5Rated 5 stars out of 5(69)

Mephisto - Clement. Color Dark Brown. $449.00.

Brown Mephisto Clement

Brown Mephisto Clement

Brand Name: Mephisto
Product Name: Clement
Gender: Men's
Color: Dark Brown
Price: $449
Rating

KEEN Utility - Cincinnati 90 Degree 8" Waterproof (Comp Toe). Color Belgian/Sandshell. $209.95. 4.0 out of 5 stars

Brown KEEN Utility Cincinnati 90 Degree 8" Waterproof (Comp Toe)

Brown KEEN Utility Cincinnati 90 Degree 8" Waterproof (Comp Toe)

Brand Name: KEEN Utility
Product Name: Cincinnati 90 Degree 8" Waterproof (Comp Toe)
Gender: Men's
Color: Belgian/Sandshell
Price: $209.95
Rating: 4Rated 4 stars out of 5(53)

KEEN Utility - Dover 8" Waterproof (Carbon-fiber Toe). Color Dark Earth/Black. $235.00. 3.9 out of 5 stars

Brown KEEN Utility Dover 8" Waterproof (Carbon-fiber Toe)

Brown KEEN Utility Dover 8" Waterproof (Carbon-fiber Toe)

Brand Name: KEEN Utility
Product Name: Dover 8" Waterproof (Carbon-fiber Toe)
Gender: Men's
Color: Dark Earth/Black
Price: $235
Rating: 4Rated 4 stars out of 5(53)

Ariat - Longview Shock Shield 8" Waterproof Composite Toe Work Boots. Color Copper Brown. $209.95. 5.0 out of 5 stars

Brown Ariat Longview Shock Shield 8" Waterproof Composite Toe Work Boots

Brown Ariat Longview Shock Shield 8" Waterproof Composite Toe Work Boots

Brand Name: Ariat
Product Name: Longview Shock Shield 8" Waterproof Composite Toe Work Boots
Gender: Men's
Color: Copper Brown
Price: $209.95
Rating: 5Rated 5 stars out of 5(2)

Zamberlan - 5020 Extinguisher II WLF. Color Black. Low Stock. $450.00. 5.0 out of 5 stars

Low Stock

Black Zamberlan 5020 Extinguisher II WLF

Black Zamberlan 5020 Extinguisher II WLF

Brand Name: Zamberlan
Product Name: 5020 Extinguisher II WLF
Gender: Men's
Color: Black
Price: $450
Rating: 5Rated 5 stars out of 5(1)

Ariat - Steadfast Cowboy Boot. Color Dusk Brown. $259.95.

Gray Ariat Steadfast Cowboy Boot

Gray Ariat Steadfast Cowboy Boot

Brand Name: Ariat
Product Name: Steadfast Cowboy Boot
Gender: Men's
Color: Dusk Brown
Price: $259.95
Rating

Allen Edmonds - Durango Zip Short Boots. Color Black. Low Stock. On sale for $416.50. MSRP $595.00. 30% off.

Low Stock

Black Allen Edmonds Durango Zip Short Boots

Black Allen Edmonds Durango Zip Short Boots

+2

Brand Name: Allen Edmonds
Product Name: Durango Zip Short Boots
Gender: Men's
Color: Black
Price: $416.50MSRP: $59530% OFF
Rating

Hoka - Kaha 3 GTX®. Color Walnut/Oyster Mushroom. Low Stock. $240.00.

Low Stock

Brown Hoka Kaha 3 GTX®

Brown Hoka Kaha 3 GTX®

Brand Name: Hoka
Product Name: Kaha 3 GTX®
Gender: Men's
Color: Walnut/Oyster Mushroom
Price: $240
Rating

Ariat - OverDrive Wide Square Toe Composite Toe Work Boots. Color Brown/Rough Stone. $239.95. 4.0 out of 5 stars

Brown Ariat OverDrive Wide Square Toe Composite Toe Work Boots

Brown Ariat OverDrive Wide Square Toe Composite Toe Work Boots

Brand Name: Ariat
Product Name: OverDrive Wide Square Toe Composite Toe Work Boots
Gender: Men's
Color: Brown/Rough Stone
Price: $239.95
Rating: 4Rated 4 stars out of 5(2)

Timberland PRO - Whitman 8 Inch Composite Safety Toe Waterproof. Color Copper Brown. On sale for $219.95. MSRP $240.00. 8% off. 3.0 out of 5 stars

Brown Timberland PRO Whitman 8 Inch Composite Safety Toe Waterproof

Brown Timberland PRO Whitman 8 Inch Composite Safety Toe Waterproof

Brand Name: Timberland PRO
Product Name: Whitman 8 Inch Composite Safety Toe Waterproof
Gender: Men's
Color: Copper Brown
Price: $219.95MSRP: $2408% OFF
Rating: 3Rated 3 stars out of 5(1)

Asolo - Nuptse GV. Color Brown 1. On sale for $440.47. MSRP $520.00. 15% off. 2.3 out of 5 stars

Brown Asolo Nuptse GV

Brown Asolo Nuptse GV

Brand Name: Asolo
Product Name: Nuptse GV
Gender: Men's
Color: Brown 1
Price: $440.47MSRP: $52015% OFF
Rating: 2Rated 2 stars out of 5(3)

KEEN Utility - Liberty 8" Waterproof Boot (Soft Toe). Color Leather Brown/Birch. Low Stock. $295.00. 4.8 out of 5 stars

Low Stock

Brown KEEN Utility Liberty 8" Waterproof Boot (Soft Toe)

Brown KEEN Utility Liberty 8" Waterproof Boot (Soft Toe)

Brand Name: KEEN Utility
Product Name: Liberty 8" Waterproof Boot (Soft Toe)
Gender: Men's
Color: Leather Brown/Birch
Price: $295
Rating: 5Rated 5 stars out of 5(4)

Ariat - Rebar Flex SD Composite Toe Work Boots. Color Distressed Brown/Stone. $209.95. 3.3 out of 5 stars

Brown Ariat Rebar Flex SD Composite Toe Work Boots

Brown Ariat Rebar Flex SD Composite Toe Work Boots

Brand Name: Ariat
Product Name: Rebar Flex SD Composite Toe Work Boots
Gender: Men's
Color: Distressed Brown/Stone
Price: $209.95
Rating: 3Rated 3 stars out of 5(3)

Timberland PRO - Boondock 8 Inch Composite Safety Toe Puncture Resistant External MetGuard. Color Black. On sale for $259.95. MSRP $280.00. 7% off.

Black Timberland PRO Boondock 8 Inch Composite Safety Toe Puncture Resistant External MetGuard

Black Timberland PRO Boondock 8 Inch Composite Safety Toe Puncture Resistant External MetGuard

Brand Name: Timberland PRO
Product Name: Boondock 8 Inch Composite Safety Toe Puncture Resistant External MetGuard
Gender: Men's
Color: Black
Price: $259.95MSRP: $2807% OFF
Rating

. KEEN Utility - Targhee IV Waterproof Work Boots (Carbon Toe). Color Magnet/Black. $244.90.

Black KEEN Utility Targhee IV Waterproof Work Boots (Carbon Toe)

Black KEEN Utility Targhee IV Waterproof Work Boots (Carbon Toe)

Brand Name: KEEN Utility
Product Name: Targhee IV Waterproof Work Boots (Carbon Toe)
Gender: Men's
Color: Magnet/Black
Price: $244.90
Rating

. KEEN Utility - Targhee IV LTR Waterproof Work Boots (Carbon Toe). Color Bison/Black. $254.90.

Brown KEEN Utility Targhee IV LTR Waterproof Work Boots (Carbon Toe)

Brown KEEN Utility Targhee IV LTR Waterproof Work Boots (Carbon Toe)

Brand Name: KEEN Utility
Product Name: Targhee IV LTR Waterproof Work Boots (Carbon Toe)
Gender: Men's
Color: Bison/Black
Price: $254.90
Rating

Cole Haan - Roundhill Grand Chukka Boots. Color Woodbury/Dark Natural/Dark Natural. Low Stock. $259.95.

Low Stock

Brown Cole Haan Roundhill Grand Chukka Boots

Brown Cole Haan Roundhill Grand Chukka Boots

+3

Brand Name: Cole Haan
Product Name: Roundhill Grand Chukka Boots
Gender: Men's
Color: Woodbury/Dark Natural/Dark Natural
Price: $259.95
Rating

Red Wing Heritage - Classic Chelsea. Color Amber Harness. $299.99. 4.1 out of 5 stars

Brown Red Wing Heritage Classic Chelsea

Brown Red Wing Heritage Classic Chelsea

+3

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

Red Wing Heritage - 6" Moc Toe. Color Oro-Legacy. $329.99. 4.5 out of 5 stars

Tan Red Wing Heritage 6" Moc Toe

Tan Red Wing Heritage 6" Moc Toe

+7

Brand Name: Red Wing Heritage
Product Name: 6" Moc Toe
Gender: Men's
Color: Oro-Legacy
Price: $329.99
Rating: 5Rated 5 stars out of 5(264)

Danner - 4" Trail 2650 Mid GTX. Color Red. $229.95. 4.0 out of 5 stars

Red Danner 4" Trail 2650 Mid GTX

Red Danner 4" Trail 2650 Mid GTX

+2

Brand Name: Danner
Product Name: 4" Trail 2650 Mid GTX
Gender: Men's
Color: Red
Price: $229.95
Rating: 4Rated 4 stars out of 5(709)

Red Wing Heritage - 6" Iron Ranger Lug. Color Amber Harness. $349.99. 4.5 out of 5 stars

Brown Red Wing Heritage 6" Iron Ranger Lug

Brown Red Wing Heritage 6" Iron Ranger Lug

+4

Brand Name: Red Wing Heritage
Product Name: 6" Iron Ranger Lug
Gender: Men's
Color: Amber Harness
Price: $349.99
Rating: 4Rated 4 stars out of 5(161)

Allen Edmonds - Tompkins. Color Brown Leather. $550.00. 3.5 out of 5 stars

Brown Allen Edmonds Tompkins

Brown Allen Edmonds Tompkins

+2

Brand Name: Allen Edmonds
Product Name: Tompkins
Gender: Men's
Color: Brown Leather
Price: $550
Rating: 4Rated 4 stars out of 5(2)

Blundstone - Dress Chelsea Boots. Color Rustic Black. $209.95. 4.0 out of 5 stars

Black Blundstone Dress Chelsea Boots

Black Blundstone Dress Chelsea Boots

+2

Brand Name: Blundstone
Product Name: Dress Chelsea Boots
Gender: Unisex
Color: Rustic Black
Price: $209.95
Rating: 4Rated 4 stars out of 5(7)

KEEN - Revel IV High Polar. Color Canteen/Black. Low Stock. $209.95. 4.0 out of 5 stars

Low Stock

Olive KEEN Revel IV High Polar

Olive KEEN Revel IV High Polar

+2

Brand Name: KEEN
Product Name: Revel IV High Polar
Gender: Men's
Color: Canteen/Black
Price: $209.95
Rating: 4Rated 4 stars out of 5(135)

Johnston & Murphy - XC+ Durham Cap Toe Boots. Color Black Waterproof Full Grain. $218.95. 4.0 out of 5 stars

Black Johnston & Murphy XC+ Durham Cap Toe Boots

Black Johnston & Murphy XC+ Durham Cap Toe Boots

+2

Brand Name: Johnston & Murphy
Product Name: XC+ Durham Cap Toe Boots
Gender: Men's
Color: Black Waterproof Full Grain
Price: $218.95
Rating: 4Rated 4 stars out of 5(1)

PIKOLINOS - York M2M-8156C1. Color Seamoss. Low Stock. On sale for $240.00. MSRP $250.00. 4% off. 5.0 out of 5 stars

Low Stock

Brown PIKOLINOS York M2M-8156C1

Brown PIKOLINOS York M2M-8156C1

Brand Name: PIKOLINOS
Product Name: York M2M-8156C1
Gender: Men's
Color: Seamoss
Price: $240MSRP: $2504% OFF
Rating: 5Rated 5 stars out of 5(1)

KEEN Utility - Cincinnati 6" Waterproof (Carbon Toe). Color Dark Chocolate/Sandshell. $200.00. 4.0 out of 5 stars

Brown KEEN Utility Cincinnati 6" Waterproof (Carbon Toe)

Brown KEEN Utility Cincinnati 6" Waterproof (Carbon Toe)

+2

Brand Name: KEEN Utility
Product Name: Cincinnati 6" Waterproof (Carbon Toe)
Gender: Men's
Color: Dark Chocolate/Sandshell
Price: $200
Rating: 4Rated 4 stars out of 5(392)

Cole Haan - Judson Grand Chelsea Boots. Color Black Waterproof/Black/Black. $259.95.

Black Cole Haan Judson Grand Chelsea Boots

Black Cole Haan Judson Grand Chelsea Boots

+2

Brand Name: Cole Haan
Product Name: Judson Grand Chelsea Boots
Gender: Men's
Color: Black Waterproof/Black/Black
Price: $259.95
Rating

Hoka - Kaha 3 GTX®. Color Sea Moss/Oat Milk. $240.00. 3.6 out of 5 stars

Khaki Hoka Kaha 3 GTX®

Khaki Hoka Kaha 3 GTX®

+2

Brand Name: Hoka
Product Name: Kaha 3 GTX®
Gender: Men's
Color: Sea Moss/Oat Milk
Price: $240
Rating: 4Rated 4 stars out of 5(18)

Red Wing Heritage - Blacksmith. Color Copper Rough & Tough. $329.99. 4.5 out of 5 stars

Tan Red Wing Heritage Blacksmith

Tan Red Wing Heritage Blacksmith

+2

Brand Name: Red Wing Heritage
Product Name: Blacksmith
Gender: Men's
Color: Copper Rough & Tough
Price: $329.99
Rating: 5Rated 5 stars out of 5(24)

Johnston & Murphy - Dudley Lug Wingtip Boots. Color Navy Multi Hand-stained Calfskin. $325.00. 3.0 out of 5 stars

Black Johnston & Murphy Dudley Lug Wingtip Boots

Black Johnston & Murphy Dudley Lug Wingtip Boots

Brand Name: Johnston & Murphy
Product Name: Dudley Lug Wingtip Boots
Gender: Men's
Color: Navy Multi Hand-stained Calfskin
Price: $325
Rating: 3Rated 3 stars out of 5(1)

Timberland PRO - Boondock Comp Toe. Color Brown 3. $219.95. 4.3 out of 5 stars

Brown Timberland PRO Boondock Comp Toe

Brown Timberland PRO Boondock Comp Toe

+2

Brand Name: Timberland PRO
Product Name: Boondock Comp Toe
Gender: Men's
Color: Brown 3
Price: $219.95
Rating: 4Rated 4 stars out of 5(582)

Allen Edmonds - Park Boot. Color Chili. Low Stock. On sale for $385.00. MSRP $550.00. 30% off. 3.9 out of 5 stars

Low Stock

Brown Allen Edmonds Park Boot

Brown Allen Edmonds Park Boot

+2

Brand Name: Allen Edmonds
Product Name: Park Boot
Gender: Men's
Color: Chili
Price: $385MSRP: $55030% OFF
Rating: 4Rated 4 stars out of 5(15)

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