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Size 8.5 Ankle Leather Leather On Sale Products

52 items found

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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)

Dansko - Frankie. Color Brown Oiled. On sale for $159.95. MSRP $179.95. 11% off. 4.2 out of 5 stars

Brown Dansko Frankie

Brown Dansko Frankie

+3

Brand Name: Dansko
Product Name: Frankie
Gender: Women's
Color: Brown Oiled
Price: $159.95MSRP: $179.9511% OFF
Rating: 4Rated 4 stars out of 5(305)

Nunn Bush - Odell 2.0 Wingtip Dress Casual Chukka Leather Boots. Color Tan. On sale for $89.95. MSRP $120.00. 25% off. 4.5 out of 5 stars

Tan Nunn Bush Odell 2.0 Wingtip Dress Casual Chukka Leather Boots

Tan Nunn Bush Odell 2.0 Wingtip Dress Casual Chukka Leather Boots

+1

Brand Name: Nunn Bush
Product Name: Odell 2.0 Wingtip Dress Casual Chukka Leather Boots
Gender: Men's
Color: Tan
Price: $89.95MSRP: $12025% OFF
Rating: 4Rated 4 stars out of 5(13)

Frye - Paul Mid Lace. Color Black. On sale for $205.20. MSRP $228.00. 10% off. 5.0 out of 5 stars

Black Frye Paul Mid Lace

Black Frye Paul Mid Lace

+3

Brand Name: Frye
Product Name: Paul Mid Lace
Gender: Men's
Color: Black
Price: $205.20MSRP: $22810% OFF
Rating: 5Rated 5 stars out of 5(1)

Clarks - Shepton. Color Black Leather. On sale for $90.00. MSRP $110.00. 18% off. 1.7 out of 5 stars

Black Clarks Shepton

Black Clarks Shepton

+6

Brand Name: Clarks
Product Name: Shepton
Gender: Men's
Color: Black Leather
Price: $90MSRP: $11018% OFF
Rating: 2Rated 2 stars out of 5(6)

Caterpillar - Striver Waterproof Steel Toe. Color Brown 1. On sale for $89.99. MSRP $100.00. 10% off. 3.4 out of 5 stars

Brown Caterpillar Striver Waterproof Steel Toe

Brown Caterpillar Striver Waterproof Steel Toe

Brand Name: Caterpillar
Product Name: Striver Waterproof Steel Toe
Gender: Men's
Color: Brown 1
Price: $89.99MSRP: $10010% OFF
Rating: 3Rated 3 stars out of 5(5)

Born - Reed. Color Brown (Wood). On sale for $119.95. MSRP $150.00. 20% off.

Brown Born Reed

Brown Born Reed

+3

Brand Name: Born
Product Name: Reed
Gender: Men's
Color: Brown (Wood)
Price: $119.95MSRP: $15020% OFF
Rating

Johnston & Murphy - Xc+ Parker Chukka. Color Brown Waterproof Full Grain. On sale for $129.99. MSRP $189.00. 31% off.

Red Johnston & Murphy Xc+ Parker Chukka

Red Johnston & Murphy Xc+ Parker Chukka

+2

Brand Name: Johnston & Murphy
Product Name: Xc+ Parker Chukka
Gender: Men's
Color: Brown Waterproof Full Grain
Price: $129.99MSRP: $18931% OFF
Rating

Frye - Barrett Lace Up. Color Black. On sale for $198.40. MSRP $248.00. 20% off. 5.0 out of 5 stars

Black Frye Barrett Lace Up

Black Frye Barrett Lace Up

+3

Brand Name: Frye
Product Name: Barrett Lace Up
Gender: Men's
Color: Black
Price: $198.40MSRP: $24820% OFF
Rating: 5Rated 5 stars out of 5(2)

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

Dunham - Brisco. Color Black Leather. On sale for $136.15. MSRP $159.95. 15% off. 4.0 out of 5 stars

Black Dunham Brisco

Black Dunham Brisco

+3

Brand Name: Dunham
Product Name: Brisco
Gender: Men's
Color: Black Leather
Price: $136.15MSRP: $159.9515% OFF
Rating: 4Rated 4 stars out of 5(1)

Florsheim - Rucci Wingtip Lace Boots. Color Black. On sale for $134.43. MSRP $155.00. 13% off. 4.9 out of 5 stars

Black Florsheim Rucci Wingtip Lace Boots

Black Florsheim Rucci Wingtip Lace Boots

+2

Brand Name: Florsheim
Product Name: Rucci Wingtip Lace Boots
Gender: Men's
Color: Black
Price: $134.43MSRP: $15513% OFF
Rating: 5Rated 5 stars out of 5(26)

Polo Ralph Lauren - Oslo High Boot. Color Black. On sale for $150.40. MSRP $188.00. 20% off. 4.2 out of 5 stars

Black Polo Ralph Lauren Oslo High Boot

Black Polo Ralph Lauren Oslo High Boot

Brand Name: Polo Ralph Lauren
Product Name: Oslo High Boot
Gender: Men's
Color: Black
Price: $150.40MSRP: $18820% OFF
Rating: 4Rated 4 stars out of 5(6)

Stacy Adams - Platt Chelsea Boots. Color Cognac. Low Stock. On sale for $82.50. MSRP $110.00. 25% off.

Low Stock

Tan Stacy Adams Platt Chelsea Boots

Tan Stacy Adams Platt Chelsea Boots

+2

Brand Name: Stacy Adams
Product Name: Platt Chelsea Boots
Gender: Men's
Color: Cognac
Price: $82.50MSRP: $11025% OFF
Rating

Timberland PRO - PRO Wedge 6 Inch Moc Soft Toe. Color Rust. On sale for $124.95. MSRP $145.00. 14% off. 4.2 out of 5 stars

Brown Timberland PRO PRO Wedge 6 Inch Moc Soft Toe

Brown Timberland PRO PRO Wedge 6 Inch Moc Soft Toe

Brand Name: Timberland PRO
Product Name: PRO Wedge 6 Inch Moc Soft Toe
Gender: Men's
Color: Rust
Price: $124.95MSRP: $14514% OFF
Rating: 4Rated 4 stars out of 5(212)

Rockport - Flynn. Color Medium Natural Leather. On sale for $119.96. MSRP $159.95. 25% off. 2.8 out of 5 stars

Brown Rockport Flynn

Brown Rockport Flynn

+2

Brand Name: Rockport
Product Name: Flynn
Gender: Men's
Color: Medium Natural Leather
Price: $119.96MSRP: $159.9525% OFF
Rating: 3Rated 3 stars out of 5(6)

Dansko - Sigourney. Color Honey Distressed. On sale for $123.95. MSRP $184.95. 33% off. 3.5 out of 5 stars

Brown Dansko Sigourney

Brown Dansko Sigourney

+2

Brand Name: Dansko
Product Name: Sigourney
Gender: Women's
Color: Honey Distressed
Price: $123.95MSRP: $184.9533% OFF
Rating: 4Rated 4 stars out of 5(30)

Steve Madden - Hatton. Color Dark Grey. Low Stock. On sale for $135.41. 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: $135.41MSRP: $17020% OFF
Rating: 4Rated 4 stars out of 5(1)

To Boot New York - Christophe. Color Grey. Low Stock. On sale for $346.50. MSRP $495.00. 30% off.

Low Stock

Gray To Boot New York Christophe

Gray To Boot New York Christophe

+3

Brand Name: To Boot New York
Product Name: Christophe
Gender: Men's
Color: Grey
Price: $346.50MSRP: $49530% OFF
Rating

Johnston & Murphy - Barrett Plain Toe Boots. Color Tan Full Grain 1. On sale for $179.10. MSRP $199.00. 10% off. 4.5 out of 5 stars

Brown Johnston & Murphy Barrett Plain Toe Boots

Brown Johnston & Murphy Barrett Plain Toe Boots

Brand Name: Johnston & Murphy
Product Name: Barrett Plain Toe Boots
Gender: Men's
Color: Tan Full Grain 1
Price: $179.10MSRP: $19910% OFF
Rating: 5Rated 5 stars out of 5(130)

Born - Ethan. Color Taupe (Avola). On sale for $119.99. MSRP $150.00. 20% off. 2.0 out of 5 stars

Taupe Born Ethan

Taupe Born Ethan

Brand Name: Born
Product Name: Ethan
Gender: Men's
Color: Taupe (Avola)
Price: $119.99MSRP: $15020% OFF
Rating: 2Rated 2 stars out of 5(1)

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

Carhartt - Gilmore WP 6" Boot. Color Coyote Nubuck. On sale for $109.96. MSRP $174.99. 37% off. 3.9 out of 5 stars

Pewter Carhartt Gilmore WP 6" Boot

Pewter Carhartt Gilmore WP 6" Boot

Brand Name: Carhartt
Product Name: Gilmore WP 6" Boot
Gender: Men's
Color: Coyote Nubuck
Price: $109.96MSRP: $174.9937% OFF
Rating: 4Rated 4 stars out of 5(9)

Born - Erik. Color Brown (Castano). On sale for $144.00. MSRP $160.00. 10% off.

Brown Born Erik

Brown Born Erik

Brand Name: Born
Product Name: Erik
Gender: Men's
Color: Brown (Castano)
Price: $144MSRP: $16010% OFF
Rating

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)

Johnston & Murphy - Latham Plain Toe Boots. Color Black European Calfskin. Low Stock. On sale for $246.00. MSRP $328.00. 25% off.

Low Stock

Black Johnston & Murphy Latham Plain Toe Boots

Black Johnston & Murphy Latham Plain Toe Boots

+2

Brand Name: Johnston & Murphy
Product Name: Latham Plain Toe Boots
Gender: Men's
Color: Black European Calfskin
Price: $246MSRP: $32825% OFF
Rating

Johnston & Murphy - Larkin Chukka. Color Tan Italian Calfskin. On sale for $99.99. MSRP $159.00. 37% off. 1.0 out of 5 stars

Tan Johnston & Murphy Larkin Chukka

Tan Johnston & Murphy Larkin Chukka

Brand Name: Johnston & Murphy
Product Name: Larkin Chukka
Gender: Men's
Color: Tan Italian Calfskin
Price: $99.99MSRP: $15937% OFF
Rating: 1Rated 1 star out of 5(1)

Eastland 1955 Edition - Chimney Pond. Color Black. On sale for $87.00. MSRP $145.00. 40% off. 5.0 out of 5 stars

Black Eastland 1955 Edition Chimney Pond

Black Eastland 1955 Edition Chimney Pond

Brand Name: Eastland 1955 Edition
Product Name: Chimney Pond
Gender: Men's
Color: Black
Price: $87MSRP: $14540% OFF
Rating: 5Rated 5 stars out of 5(1)

L.L.Bean - Allagash Handsewn Chukka Boot. Color Canyon. On sale for $143.99. MSRP $180.00. 20% off. 3.9 out of 5 stars

Multi L.L.Bean Allagash Handsewn Chukka Boot

Multi L.L.Bean Allagash Handsewn Chukka Boot

+2

Brand Name: L.L.Bean
Product Name: Allagash Handsewn Chukka Boot
Gender: Men's
Color: Canyon
Price: $143.99MSRP: $18020% OFF
Rating: 4Rated 4 stars out of 5(35)

Taft - Lewis. Color Oro Viejo. On sale for $295.00. MSRP $349.00. 15% off.

Brown Taft Lewis

Brown Taft Lewis

Brand Name: Taft
Product Name: Lewis
Gender: Men's
Color: Oro Viejo
Price: $295MSRP: $34915% OFF
Rating

Orthofeet - Verno. Color Black. Low Stock. On sale for $104.00. MSRP $160.00. 35% off.

Low Stock

Black Orthofeet Verno

Black Orthofeet Verno

Brand Name: Orthofeet
Product Name: Verno
Gender: Men's
Color: Black
Price: $104MSRP: $16035% OFF
Rating

Frye - Hudson Workboot Plain Toe. Color Whiskey. On sale for $294.40. MSRP $368.00. 20% off. 4.0 out of 5 stars

Brown Frye Hudson Workboot Plain Toe

Brown Frye Hudson Workboot Plain Toe

+2

Brand Name: Frye
Product Name: Hudson Workboot Plain Toe
Gender: Men's
Color: Whiskey
Price: $294.40MSRP: $36820% OFF
Rating: 4Rated 4 stars out of 5(3)

Dan Post - Winslow. Color Dark Brown/Blue. Low Stock. On sale for $179.99. MSRP $249.95. 28% off. 4.2 out of 5 stars

Low Stock

Brown Dan Post Winslow

Brown Dan Post Winslow

Brand Name: Dan Post
Product Name: Winslow
Gender: Men's
Color: Dark Brown/Blue
Price: $179.99MSRP: $249.9528% OFF
Rating: 4Rated 4 stars out of 5(12)

Steve Madden - Millsen. Color Tan. Low Stock. On sale for $91.00. MSRP $130.00. 30% off.

Low Stock

Tan Steve Madden Millsen

Tan Steve Madden Millsen

Brand Name: Steve Madden
Product Name: Millsen
Gender: Men's
Color: Tan
Price: $91MSRP: $13030% OFF
Rating

Martin Dingman - Blue Ridge Chukka Boot. Color Camo. Low Stock. On sale for $132.75. MSRP $295.00. 55% off.

Low Stock

Multi Martin Dingman Blue Ridge Chukka Boot

Multi Martin Dingman Blue Ridge Chukka Boot

+3

Brand Name: Martin Dingman
Product Name: Blue Ridge Chukka Boot
Gender: Men's
Color: Camo
Price: $132.75MSRP: $29555% OFF
Rating

Clarks - Wallabee Boots. Color Black Leather. On sale for $130.00. MSRP $150.00. 13% off. 4.5 out of 5 stars

Black Clarks Wallabee Boots

Black Clarks Wallabee Boots

+4

Brand Name: Clarks
Product Name: Wallabee Boots
Gender: Men's
Color: Black Leather
Price: $130MSRP: $15013% OFF
Rating: 4Rated 4 stars out of 5(62)

Allen Edmonds - Tompkins. Color Snuff Suede. On sale for $379.00. MSRP $495.00. 23% off. 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: Snuff Suede
Price: $379MSRP: $49523% OFF
Rating: 4Rated 4 stars out of 5(2)

Stacy Adams - Madison Cap Toe Lace-Up Boots. Color Cognac. On sale for $131.25. MSRP $175.00. 25% off. 5.0 out of 5 stars

Tan Stacy Adams Madison Cap Toe Lace-Up Boots

Tan Stacy Adams Madison Cap Toe Lace-Up Boots

+4

Brand Name: Stacy Adams
Product Name: Madison Cap Toe Lace-Up Boots
Gender: Men's
Color: Cognac
Price: $131.25MSRP: $17525% OFF
Rating: 5Rated 5 stars out of 5(1)

Tommy Hilfiger - Bage. Color Dark Brown. On sale for $89.25. MSRP $119.00. 25% off. 4.5 out of 5 stars

Brown Tommy Hilfiger Bage

Brown Tommy Hilfiger Bage

+4

Brand Name: Tommy Hilfiger
Product Name: Bage
Gender: Men's
Color: Dark Brown
Price: $89.25MSRP: $11925% OFF
Rating: 5Rated 5 stars out of 5(2)

Frye - Paul Chukka. Color Mushroom. Low Stock. On sale for $150.40. MSRP $188.00. 20% off. 4.0 out of 5 stars

Low Stock

Neutral Frye Paul Chukka

Neutral Frye Paul Chukka

+2

Brand Name: Frye
Product Name: Paul Chukka
Gender: Men's
Color: Mushroom
Price: $150.40MSRP: $18820% OFF
Rating: 4Rated 4 stars out of 5(3)

Cole Haan - American Classics Chelsea Boots. Color Morel Nubuck Waterproof/Black. On sale for $119.95. MSRP $200.00. 40% off.

Taupe Cole Haan American Classics Chelsea Boots

Taupe Cole Haan American Classics Chelsea Boots

+3

Brand Name: Cole Haan
Product Name: American Classics Chelsea Boots
Gender: Men's
Color: Morel Nubuck Waterproof/Black
Price: $119.95MSRP: $20040% OFF
Rating

Dansko - Delphine. Color Black Waterproof Burnished. On sale for $120.97. MSRP $219.95. 45% off. 4.2 out of 5 stars

Black Dansko Delphine

Black Dansko Delphine

+2

Brand Name: Dansko
Product Name: Delphine
Gender: Women's
Color: Black Waterproof Burnished
Price: $120.97MSRP: $219.9545% OFF
Rating: 4Rated 4 stars out of 5(6)

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)

Florsheim - Rucci Plain Toe Chukka Boot. Color Brown Smooth. On sale for $134.95. MSRP $155.00. 13% off. 4.3 out of 5 stars

Brown Florsheim Rucci Plain Toe Chukka Boot

Brown Florsheim Rucci Plain Toe Chukka Boot

Brand Name: Florsheim
Product Name: Rucci Plain Toe Chukka Boot
Gender: Men's
Color: Brown Smooth
Price: $134.95MSRP: $15513% OFF
Rating: 4Rated 4 stars out of 5(51)

Frye - Tyler Flex Lace Up. Color Black. On sale for $206.40. MSRP $258.00. 20% off. 4.2 out of 5 stars

Black Frye Tyler Flex Lace Up

Black Frye Tyler Flex Lace Up

Brand Name: Frye
Product Name: Tyler Flex Lace Up
Gender: Men's
Color: Black
Price: $206.40MSRP: $25820% OFF
Rating: 4Rated 4 stars out of 5(4)

Martin Dingman - Bad Weather Boot. Color Chestnut 1. On sale for $256.75. MSRP $395.00. 35% off.

Khaki Martin Dingman Bad Weather Boot

Khaki Martin Dingman Bad Weather Boot

+2

Brand Name: Martin Dingman
Product Name: Bad Weather Boot
Gender: Men's
Color: Chestnut 1
Price: $256.75MSRP: $39535% OFF
Rating

Dansko - Tony. Color Tan. On sale for $129.98. MSRP $194.95. 33% off.

Tan Dansko Tony

Tan Dansko Tony

+2

Brand Name: Dansko
Product Name: Tony
Gender: Men's
Color: Tan
Price: $129.98MSRP: $194.9533% OFF
Rating

Martin Dingman - Huntley Chelsea Boot. Color French Roast 1. On sale for $227.50. MSRP $350.00. 35% off.

Tan Martin Dingman Huntley Chelsea Boot

Tan Martin Dingman Huntley Chelsea Boot

+2

Brand Name: Martin Dingman
Product Name: Huntley Chelsea Boot
Gender: Men's
Color: French Roast 1
Price: $227.50MSRP: $35035% OFF
Rating

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)

Johnston & Murphy - Bolivar Plain Toe Boots. Color Snuff Italian Suede. Low Stock. On sale for $114.00. MSRP $285.00. 60% off.

Low Stock

Brown Johnston & Murphy Bolivar Plain Toe Boots

Brown Johnston & Murphy Bolivar Plain Toe Boots

Brand Name: Johnston & Murphy
Product Name: Bolivar Plain Toe Boots
Gender: Men's
Color: Snuff Italian Suede
Price: $114MSRP: $28560% OFF
Rating

Steve Madden - Noby. Color Grey. On sale for $154.41. MSRP $175.00. 12% off. 3.2 out of 5 stars

Gray Steve Madden Noby

Gray Steve Madden Noby

+1

Brand Name: Steve Madden
Product Name: Noby
Gender: Men's
Color: Grey
Price: $154.41MSRP: $17512% OFF
Rating: 3Rated 3 stars out of 5(4)

Johnston & Murphy - Brody Chukka. Color Snuff Suede. Low Stock. On sale for $115.00. MSRP $165.00. 30% off.

Low Stock

Brown Johnston & Murphy Brody Chukka

Brown Johnston & Murphy Brody Chukka

Brand Name: Johnston & Murphy
Product Name: Brody Chukka
Gender: Men's
Color: Snuff Suede
Price: $115MSRP: $16530% OFF
Rating

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