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

Size 8.5 Leather Outsole Products

38 items found

Sort By

Your Selections

Search Results

Cole Haan - Pinch Penny. Color Black. On sale for $112.00. MSRP $160.00.. 4.1 out of 5 stars

Black Cole Haan Pinch Penny

Black Cole Haan Pinch Penny

Brand Name: Cole Haan
Product Name: Pinch Penny
Gender: Men's
Color: Black
Price: $112.00MSRP: $160.00
Rating: 4Rated 4 stars out of 5(166)

Cole Haan - Pinch Tassel. Color Black. On sale for $135.00. MSRP $140.00.. 4.0 out of 5 stars

Black Cole Haan Pinch Tassel

Black Cole Haan Pinch Tassel

Brand Name: Cole Haan
Product Name: Pinch Tassel
Gender: Men's
Color: Black
Price: $135.00MSRP: $140.00
Rating: 4Rated 4 stars out of 5(232)

Frye - Chris Venetian. Color Tan Oiled Vintage. On sale for $228.00. MSRP $238.00.. 4.1 out of 5 stars

Brown Frye Chris Venetian

Brown Frye Chris Venetian

+5

Brand Name: Frye
Product Name: Chris Venetian
Gender: Men's
Color: Tan Oiled Vintage
Price: $228.00MSRP: $238.00
Rating: 4Rated 4 stars out of 5(17)

Florsheim - Conetta Cap Toe Oxford. Color Black. On sale for $124.95. MSRP $150.00.. 4.8 out of 5 stars

Black Florsheim Conetta Cap Toe Oxford

Black Florsheim Conetta Cap Toe Oxford

+2

Brand Name: Florsheim
Product Name: Conetta Cap Toe Oxford
Gender: Men's
Color: Black
Price: $124.95MSRP: $150.00
Rating: 5Rated 5 stars out of 5(15)

Johnston & Murphy - Hayes Penny Loafer. Color Burgundy. On sale for $99.99. MSRP $135.00.. 4.1 out of 5 stars

Burgundy Johnston & Murphy Hayes Penny Loafer

Burgundy Johnston & Murphy Hayes Penny Loafer

+2

Brand Name: Johnston & Murphy
Product Name: Hayes Penny Loafer
Gender: Men's
Color: Burgundy
Price: $99.99MSRP: $135.00
Rating: 4Rated 4 stars out of 5(59)

Massimo Matteo - Moccasin Loafers. Color Madiera. On sale for $43.60. MSRP $109.00..

Blue Massimo Matteo Moccasin Loafers

Blue Massimo Matteo Moccasin Loafers

+2

Brand Name: Massimo Matteo
Product Name: Moccasin Loafers
Gender: Men's
Color: Madiera
Price: $43.60MSRP: $109.00
Rating

Nunn Bush - MAC Moccasin Toe Oxford. Color Black. On sale for $69.95. MSRP $100.00.. 5.0 out of 5 stars

Black Nunn Bush MAC Moccasin Toe Oxford

Black Nunn Bush MAC Moccasin Toe Oxford

+2

Brand Name: Nunn Bush
Product Name: MAC Moccasin Toe Oxford
Gender: Men's
Color: Black
Price: $69.95MSRP: $100.00
Rating: 5Rated 5 stars out of 5(2)

Massimo Matteo - Corazzano Wing Tip. Color Cioccolato. Low Stock. On sale for $77.33. MSRP $209.00..

4 left in stock

Brown Massimo Matteo Corazzano Wing Tip

Brown Massimo Matteo Corazzano Wing Tip

Brand Name: Massimo Matteo
Product Name: Corazzano Wing Tip
Gender: Men's
Color: Cioccolato
Price: $77.33MSRP: $209.00
Rating

Magnanni - Lachlan. Color Grey/Cuero. On sale for $244.75. MSRP $445.00..

Black Magnanni Lachlan

Black Magnanni Lachlan

Brand Name: Magnanni
Product Name: Lachlan
Gender: Men's
Color: Grey/Cuero
Price: $244.75MSRP: $445.00
Rating

Massimo Matteo - 4-Eye Blucher Classic 24. Color Black. Low Stock. On sale for $69.32. MSRP $114.95..

5 left in stock

Black Massimo Matteo 4-Eye Blucher Classic 24

Black Massimo Matteo 4-Eye Blucher Classic 24

+2

Brand Name: Massimo Matteo
Product Name: 4-Eye Blucher Classic 24
Gender: Men's
Color: Black
Price: $69.32MSRP: $114.95
Rating

Cole Haan - Washington Grand Laser Wing Oxford. Color British Tan/Lava Energy. On sale for $294.81. MSRP $400.00.. 4.5 out of 5 stars

Tan Cole Haan Washington Grand Laser Wing Oxford

Tan Cole Haan Washington Grand Laser Wing Oxford

+3

Brand Name: Cole Haan
Product Name: Washington Grand Laser Wing Oxford
Gender: Men's
Color: British Tan/Lava Energy
Price: $294.81MSRP: $400.00
Rating: 4Rated 4 stars out of 5(190)

Magnanni - Landon. Color Black 1. On sale for $246.11. MSRP $435.00.. 3.7 out of 5 stars

Black Magnanni Landon

Black Magnanni Landon

Brand Name: Magnanni
Product Name: Landon
Gender: Men's
Color: Black 1
Price: $246.11MSRP: $435.00
Rating: 4Rated 4 stars out of 5(3)

Florsheim - Como Slip-On Loafer. Color Black. On sale for $119.95. MSRP $130.00.. 4.5 out of 5 stars

Black Florsheim Como Slip-On Loafer

Black Florsheim Como Slip-On Loafer

Brand Name: Florsheim
Product Name: Como Slip-On Loafer
Gender: Men's
Color: Black
Price: $119.95MSRP: $130.00
Rating: 4Rated 4 stars out of 5(514)

Tommy Hilfiger - Hines. Color Navy. On sale for $59.40. MSRP $69.95..

Navy Tommy Hilfiger Hines

Navy Tommy Hilfiger Hines

+4

Brand Name: Tommy Hilfiger
Product Name: Hines
Gender: Men's
Color: Navy
Price: $59.40MSRP: $69.95
Rating

Stacy Adams - Valet Velour Slip-On Loafer. Color Black. Low Stock. On sale for $64.32. MSRP $94.95.. 4.5 out of 5 stars

9 left in stock

Black Stacy Adams Valet Velour Slip-On Loafer

Black Stacy Adams Valet Velour Slip-On Loafer

+3

Brand Name: Stacy Adams
Product Name: Valet Velour Slip-On Loafer
Gender: Men's
Color: Black
Price: $64.32MSRP: $94.95
Rating: 5Rated 5 stars out of 5(107)

COACH - Cooper Loafer. Color Black. On sale for $192.50. MSRP $275.00..

Black COACH Cooper Loafer

Black COACH Cooper Loafer

+4

Brand Name: COACH
Product Name: Cooper Loafer
Gender: Men's
Color: Black
Price: $192.50MSRP: $275.00
Rating

Florsheim - Kenmoor Wingtip Oxford. Color Heritage Calf Black. On sale for $234.95. MSRP $250.00.. 4.5 out of 5 stars

Black Florsheim Kenmoor Wingtip Oxford

Black Florsheim Kenmoor Wingtip Oxford

Brand Name: Florsheim
Product Name: Kenmoor Wingtip Oxford
Gender: Men's
Color: Heritage Calf Black
Price: $234.95MSRP: $250.00
Rating: 5Rated 5 stars out of 5(862)

Corral Boots - C3988. Color Black. Low Stock. On sale for $156.29. MSRP $319.00.. 1.0 out of 5 stars

6 left in stock

Black Corral Boots C3988

Black Corral Boots C3988

Brand Name: Corral Boots
Product Name: C3988
Gender: Men's
Color: Black
Price: $156.29MSRP: $319.00
Rating: 1Rated 1 star out of 5(1)

Magnanni - Crucero. Color Cognac Suede. On sale for $357.43. MSRP $399.00.. 4.8 out of 5 stars

Brown Magnanni Crucero

Brown Magnanni Crucero

+4

Brand Name: Magnanni
Product Name: Crucero
Gender: Men's
Color: Cognac Suede
Price: $357.43MSRP: $399.00
Rating: 5Rated 5 stars out of 5(6)

Anthony Veer - Filmore Bit Loafer. Color Oxblood. On sale for $115.99. MSRP $164.95.. 4.0 out of 5 stars

Red Anthony Veer Filmore Bit Loafer

Red Anthony Veer Filmore Bit Loafer

+3

Brand Name: Anthony Veer
Product Name: Filmore Bit Loafer
Gender: Men's
Color: Oxblood
Price: $115.99MSRP: $164.95
Rating: 4Rated 4 stars out of 5(14)

Anthony Veer - Kennedy Tassel Loafer. Color Tan. On sale for $139.99. MSRP $199.95.. 3.9 out of 5 stars

Tan Anthony Veer Kennedy Tassel Loafer

Tan Anthony Veer Kennedy Tassel Loafer

+2

Brand Name: Anthony Veer
Product Name: Kennedy Tassel Loafer
Gender: Men's
Color: Tan
Price: $139.99MSRP: $199.95
Rating: 4Rated 4 stars out of 5(7)

Clarks - Un Shire Hi Waterproof. Color Dark Brown Leather. On sale for $98.81. MSRP $160.00.. 3.0 out of 5 stars

Brown Clarks Un Shire Hi Waterproof

Brown Clarks Un Shire Hi Waterproof

Brand Name: Clarks
Product Name: Un Shire Hi Waterproof
Gender: Men's
Color: Dark Brown Leather
Price: $98.81MSRP: $160.00
Rating: 3Rated 3 stars out of 5(1)

To Boot New York - Levanzo. Color Bruciato. Low Stock. On sale for $240.98. MSRP $425.00..

3 left in stock

Brown To Boot New York Levanzo

Brown To Boot New York Levanzo

+2

Brand Name: To Boot New York
Product Name: Levanzo
Gender: Men's
Color: Bruciato
Price: $240.98MSRP: $425.00
Rating

Ariat - Circuit Thunderbird Chimayo Western Boot. Color Saddle Up Brown. Low Stock. On sale for $149.97. MSRP $249.95.. 4.4 out of 5 stars

6 left in stock

Brown Ariat Circuit Thunderbird Chimayo Western Boot

Brown Ariat Circuit Thunderbird Chimayo Western Boot

Brand Name: Ariat
Product Name: Circuit Thunderbird Chimayo Western Boot
Gender: Men's
Color: Saddle Up Brown
Price: $149.97MSRP: $249.95
Rating: 5Rated 5 stars out of 5(23)

Marc Joseph New York - South Street. Color Black Grainy. On sale for $79.95. MSRP $155.00..

Black Marc Joseph New York South Street

Black Marc Joseph New York South Street

Brand Name: Marc Joseph New York
Product Name: South Street
Gender: Men's
Color: Black Grainy
Price: $79.95MSRP: $155.00
Rating

Stacy Adams - Riccardi Lace-Up Oxford. Color Black. On sale for $94.08. MSRP $105.00.. 4.7 out of 5 stars

Black Stacy Adams Riccardi Lace-Up Oxford

Black Stacy Adams Riccardi Lace-Up Oxford

+3

Brand Name: Stacy Adams
Product Name: Riccardi Lace-Up Oxford
Gender: Men's
Color: Black
Price: $94.08MSRP: $105.00
Rating: 5Rated 5 stars out of 5(39)

Stacy Adams - Gallinari Wingtip Lace Up. Color Black/Gray/White. On sale for $79.67. MSRP $104.95.. 4.0 out of 5 stars

Gray Stacy Adams Gallinari Wingtip Lace Up

Gray Stacy Adams Gallinari Wingtip Lace Up

+2

Brand Name: Stacy Adams
Product Name: Gallinari Wingtip Lace Up
Gender: Men's
Color: Black/Gray/White
Price: $79.67MSRP: $104.95
Rating: 4Rated 4 stars out of 5(5)

Marc Joseph New York - Duane Street. Color Grey Suede Leather. Low Stock. On sale for $58.50. MSRP $195.00.. 4.2 out of 5 stars

9 left in stock

Gray Marc Joseph New York Duane Street

Gray Marc Joseph New York Duane Street

+2

Brand Name: Marc Joseph New York
Product Name: Duane Street
Gender: Men's
Color: Grey Suede Leather
Price: $58.50MSRP: $195.00
Rating: 4Rated 4 stars out of 5(4)

Stacy Adams - Trubiano Moc Toe Oxford. Color Gray. Low Stock. On sale for $77.89. MSRP $105.00.. 4.9 out of 5 stars

8 left in stock

Gray Stacy Adams Trubiano Moc Toe Oxford

Gray Stacy Adams Trubiano Moc Toe Oxford

Brand Name: Stacy Adams
Product Name: Trubiano Moc Toe Oxford
Gender: Men's
Color: Gray
Price: $77.89MSRP: $105.00
Rating: 5Rated 5 stars out of 5(12)

Massimo Matteo - Corazzano Penny Loafer. Color Navy. Low Stock. On sale for $169.15. MSRP $199.00.. 5.0 out of 5 stars

5 left in stock

Navy Massimo Matteo Corazzano Penny Loafer

Navy Massimo Matteo Corazzano Penny Loafer

+2

Brand Name: Massimo Matteo
Product Name: Corazzano Penny Loafer
Gender: Men's
Color: Navy
Price: $169.15MSRP: $199.00
Rating: 5Rated 5 stars out of 5(4)

Massimo Matteo - Velour Penny Loafer. Color Grigio. Low Stock. On sale for $137.31. MSRP $199.00.. 4.3 out of 5 stars

5 left in stock

Khaki Massimo Matteo Velour Penny Loafer

Khaki Massimo Matteo Velour Penny Loafer

+3

Brand Name: Massimo Matteo
Product Name: Velour Penny Loafer
Gender: Men's
Color: Grigio
Price: $137.31MSRP: $199.00
Rating: 4Rated 4 stars out of 5(7)

Anthony Veer - Sherman Penny Loafer. Color Chocolate Brown. On sale for $125.61. MSRP $149.90.. 5.0 out of 5 stars

Brown Anthony Veer Sherman Penny Loafer

Brown Anthony Veer Sherman Penny Loafer

Brand Name: Anthony Veer
Product Name: Sherman Penny Loafer
Gender: Men's
Color: Chocolate Brown
Price: $125.61MSRP: $149.90
Rating: 5Rated 5 stars out of 5(3)

Acorn - Polar Pair. Color Dark Pine. On sale for $40.17. MSRP $55.00.. 4.8 out of 5 stars

Green Acorn Polar Pair

Green Acorn Polar Pair

+2

Brand Name: Acorn
Product Name: Polar Pair
Gender: Men's
Color: Dark Pine
Price: $40.17MSRP: $55.00
Rating: 5Rated 5 stars out of 5(58)

To Boot New York - Richard. Color Black. Low Stock. On sale for $315.00. MSRP $450.00..

1 left in stock

Black To Boot New York Richard

Black To Boot New York Richard

+1

Brand Name: To Boot New York
Product Name: Richard
Gender: Men's
Color: Black
Price: $315.00MSRP: $450.00
Rating

Johnston & Murphy Collection - Ellsworth Plain Toe Medallion. Color Black Italian Calfskin. On sale for $241.90. MSRP $295.00.. 2.0 out of 5 stars

Black Johnston & Murphy Collection Ellsworth Plain Toe Medallion

Black Johnston & Murphy Collection Ellsworth Plain Toe Medallion

Brand Name: Johnston & Murphy Collection
Product Name: Ellsworth Plain Toe Medallion
Gender: Men's
Color: Black Italian Calfskin
Price: $241.90MSRP: $295.00
Rating: 2Rated 2 stars out of 5(1)

Roper - Parker II. Color Brown. On sale for $176.24. MSRP $234.99..

Brown Roper Parker II

Brown Roper Parker II

Brand Name: Roper
Product Name: Parker II
Gender: Men's
Color: Brown
Price: $176.24MSRP: $234.99
Rating

Stacy Adams - Madison (Cap Toe). Color Black. Low Stock. On sale for $105.00. MSRP $129.95.. 4.6 out of 5 stars

4 left in stock

Black Stacy Adams Madison (Cap Toe)

Black Stacy Adams Madison (Cap Toe)

Brand Name: Stacy Adams
Product Name: Madison (Cap Toe)
Gender: Men's
Color: Black
Price: $105.00MSRP: $129.95
Rating: 5Rated 5 stars out of 5(805)

Stacy Adams - Gennaro Wing Tip Oxford. Color Black. Low Stock. On sale for $86.73. MSRP $104.95.. 4.8 out of 5 stars

3 left in stock

Black Stacy Adams Gennaro Wing Tip Oxford

Black Stacy Adams Gennaro Wing Tip Oxford

+1

Brand Name: Stacy Adams
Product Name: Gennaro Wing Tip Oxford
Gender: Men's
Color: Black
Price: $86.73MSRP: $104.95
Rating: 5Rated 5 stars out of 5(64)

Get on the List

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