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

Size 8.5 Leather Outsole Shoes On Sale

40 items found

Sort By

Your Selections

Search Results

Vans - Classic Slip On Checkerboard. Color Checkerboard Crystal Blue. On sale for $48.71. MSRP $65.00. 25% off. 4.6 out of 5 stars

White Vans Classic Slip On Checkerboard

White Vans Classic Slip On Checkerboard

+16

Brand Name: Vans
Product Name: Classic Slip On Checkerboard
Gender: Unisex
Color: Checkerboard Crystal Blue
Price: $48.71MSRP: $65.0025% OFF
Rating: 5Rated 5 stars out of 5(6060)

OluKai - Moloa. Color Dark Wood/Dark Java. On sale for $124.95. MSRP $140.00. 11% off. 4.4 out of 5 stars

Taupe OluKai Moloa

Taupe OluKai Moloa

+3

Brand Name: OluKai
Product Name: Moloa
Gender: Men's
Color: Dark Wood/Dark Java
Price: $124.95MSRP: $140.0011% OFF
Rating: 4Rated 4 stars out of 5(609)

Johnston & Murphy - Hayes Penny Loafer. Color Black. On sale for $99.90. MSRP $135.00. 26% off. 4.1 out of 5 stars

Black Johnston & Murphy Hayes Penny Loafer

Black Johnston & Murphy Hayes Penny Loafer

+2

Brand Name: Johnston & Murphy
Product Name: Hayes Penny Loafer
Gender: Men's
Color: Black
Price: $99.90MSRP: $135.0026% OFF
Rating: 4Rated 4 stars out of 5(116)

Vans - Hylane. Color Retro Skate Navy. On sale for $71.96. MSRP $90.00. 20% off.

Navy Vans Hylane

Navy Vans Hylane

+2

Brand Name: Vans
Product Name: Hylane
Gender: Unisex
Color: Retro Skate Navy
Price: $71.96MSRP: $90.0020% OFF
Rating

Cole Haan - American Classics Montrose Plain Toe Ox. Color Titanium Nubuck/Angora. On sale for $152.00. MSRP $190.00. 20% off.

Gray Cole Haan American Classics Montrose Plain Toe Ox

Gray Cole Haan American Classics Montrose Plain Toe Ox

Brand Name: Cole Haan
Product Name: American Classics Montrose Plain Toe Ox
Gender: Men's
Color: Titanium Nubuck/Angora
Price: $152.00MSRP: $190.0020% OFF
Rating

Cole Haan - Grandpro Luxe Slip-On Sneakers. Color Black/Ivory. On sale for $160.00. MSRP $170.00. 6% off. 3.2 out of 5 stars

Black Cole Haan Grandpro Luxe Slip-On Sneakers

Black Cole Haan Grandpro Luxe Slip-On Sneakers

+6

Brand Name: Cole Haan
Product Name: Grandpro Luxe Slip-On Sneakers
Gender: Men's
Color: Black/Ivory
Price: $160.00MSRP: $170.006% OFF
Rating: 3Rated 3 stars out of 5(4)

Johnston & Murphy - Hayes Tassel Loafer. Color Burgundy. On sale for $99.90. MSRP $135.00. 26% off. 3.9 out of 5 stars

Burgundy Johnston & Murphy Hayes Tassel Loafer

Burgundy Johnston & Murphy Hayes Tassel Loafer

+2 colors/patterns

Brand Name: Johnston & Murphy
Product Name: Hayes Tassel Loafer
Gender: Men's
Color: Burgundy
Price: $99.90MSRP: $135.0026% OFF
Rating: 4Rated 4 stars out of 5(107)

Cole Haan - Grandpro Ashland 2 Golf. Color Black/New Caramel/Ivory. On sale for $125.90. MSRP $155.00. 19% off.

Black Cole Haan Grandpro Ashland 2 Golf

Black Cole Haan Grandpro Ashland 2 Golf

+3

Brand Name: Cole Haan
Product Name: Grandpro Ashland 2 Golf
Gender: Men's
Color: Black/New Caramel/Ivory
Price: $125.90MSRP: $155.0019% OFF
Rating

Marc Joseph New York - South Street. Color Cognac Grainy. On sale for $59.95. MSRP $155.00. 61% off. 1.0 out of 5 stars

Brown Marc Joseph New York South Street

Brown Marc Joseph New York South Street

Brand Name: Marc Joseph New York
Product Name: South Street
Gender: Men's
Color: Cognac Grainy
Price: $59.95MSRP: $155.0061% OFF
Rating: 1Rated 1 star out of 5(1)

Tommy Hilfiger - Rezz6. Color Black. On sale for $62.30. MSRP $89.00. 30% off.

Black Tommy Hilfiger Rezz6

Black Tommy Hilfiger Rezz6

Brand Name: Tommy Hilfiger
Product Name: Rezz6
Gender: Men's
Color: Black
Price: $62.30MSRP: $89.0030% OFF
Rating

Cole Haan - Grand Crosscourt Modern Perforated Lace To Toe Sneakers. Color Black/Ivory. On sale for $153.00. MSRP $170.00. 10% off. 5.0 out of 5 stars

Black Cole Haan Grand Crosscourt Modern Perforated Lace To Toe Sneakers

Black Cole Haan Grand Crosscourt Modern Perforated Lace To Toe Sneakers

+4

Brand Name: Cole Haan
Product Name: Grand Crosscourt Modern Perforated Lace To Toe Sneakers
Gender: Men's
Color: Black/Ivory
Price: $153.00MSRP: $170.0010% OFF
Rating: 5Rated 5 stars out of 5(1)

. Florsheim - Berkley Penny Loafer. Color Black. On sale for $124.95. MSRP $130.00. 4% off. 4.1 out of 5 stars

Black Florsheim Berkley Penny Loafer

Black Florsheim Berkley Penny Loafer

+2

Brand Name: Florsheim
Product Name: Berkley Penny Loafer
Gender: Men's
Color: Black
Price: $124.95MSRP: $130.004% OFF
Rating: 4Rated 4 stars out of 5(1322)

Cole Haan - Pinch Penny. Color Burgundy. On sale for $135.00. MSRP $218.00. 38% off. 4.1 out of 5 stars

Burgundy Cole Haan Pinch Penny

Burgundy Cole Haan Pinch Penny

Brand Name: Cole Haan
Product Name: Pinch Penny
Gender: Men's
Color: Burgundy
Price: $135.00MSRP: $218.0038% OFF
Rating: 4Rated 4 stars out of 5(171)

Cole Haan - Pinch Tassel. Color Burgundy. On sale for $135.00. MSRP $218.00. 38% off. 4.0 out of 5 stars

Burgundy Cole Haan Pinch Tassel

Burgundy Cole Haan Pinch Tassel

Brand Name: Cole Haan
Product Name: Pinch Tassel
Gender: Men's
Color: Burgundy
Price: $135.00MSRP: $218.0038% OFF
Rating: 4Rated 4 stars out of 5(243)

Florsheim - Como Imperial Slip-On Loafer. Color Black Cabaret. On sale for $129.95. MSRP $200.00. 35% off. 4.4 out of 5 stars

Black Florsheim Como Imperial Slip-On Loafer

Black Florsheim Como Imperial Slip-On Loafer

Brand Name: Florsheim
Product Name: Como Imperial Slip-On Loafer
Gender: Men's
Color: Black Cabaret
Price: $129.95MSRP: $200.0035% OFF
Rating: 4Rated 4 stars out of 5(494)

Stacy Adams - Tristano Bike Toe Lace-Up. Color White. Low Stock. On sale for $92.27. MSRP $105.00. 12% off.

Low Stock

White Stacy Adams Tristano Bike Toe Lace-Up

White Stacy Adams Tristano Bike Toe Lace-Up

+7

Brand Name: Stacy Adams
Product Name: Tristano Bike Toe Lace-Up
Gender: Men's
Color: White
Price: $92.27MSRP: $105.0012% OFF
Rating

Orthofeet - Pacific Palisades. Color White. On sale for $109.99. MSRP $149.95. 27% off. 4.0 out of 5 stars

White Orthofeet Pacific Palisades

White Orthofeet Pacific Palisades

Brand Name: Orthofeet
Product Name: Pacific Palisades
Gender: Men's
Color: White
Price: $109.99MSRP: $149.9527% OFF
Rating: 4Rated 4 stars out of 5(2)

Marc Joseph New York - BROADWAY. Color Off White Suede. On sale for $115.50. MSRP $165.00. 30% off.

Bone Marc Joseph New York BROADWAY

Bone Marc Joseph New York BROADWAY

+6

Brand Name: Marc Joseph New York
Product Name: BROADWAY
Gender: Men's
Color: Off White Suede
Price: $115.50MSRP: $165.0030% OFF
Rating

Marc Joseph New York - Morrisville. Color Cappuccino Suede. Low Stock. On sale for $89.95. MSRP $185.00. 51% off. 5.0 out of 5 stars

Low Stock

Brown Marc Joseph New York Morrisville

Brown Marc Joseph New York Morrisville

+3

Brand Name: Marc Joseph New York
Product Name: Morrisville
Gender: Men's
Color: Cappuccino Suede
Price: $89.95MSRP: $185.0051% OFF
Rating: 5Rated 5 stars out of 5(1)

Tommy Hilfiger - Rezz. Color Dark Blue. On sale for $54.97. MSRP $89.00. 38% off. 5.0 out of 5 stars

Blue Tommy Hilfiger Rezz

Blue Tommy Hilfiger Rezz

+3

Brand Name: Tommy Hilfiger
Product Name: Rezz
Gender: Men's
Color: Dark Blue
Price: $54.97MSRP: $89.0038% OFF
Rating: 5Rated 5 stars out of 5(3)

Marc Joseph New York - Canal St 2.0. Color Black Napa. Low Stock. On sale for $171.60. MSRP $195.00. 12% off.

Low Stock

Black Marc Joseph New York Canal St 2.0

Black Marc Joseph New York Canal St 2.0

+2

Brand Name: Marc Joseph New York
Product Name: Canal St 2.0
Gender: Men's
Color: Black Napa
Price: $171.60MSRP: $195.0012% OFF
Rating

Volcom - Street Shield 8" Tactical Boots with Side Zipper. Color Black. On sale for $121.56. MSRP $152.00. 20% off.

Black Volcom Street Shield 8" Tactical Boots with Side Zipper

Black Volcom Street Shield 8" Tactical Boots with Side Zipper

Brand Name: Volcom
Product Name: Street Shield 8" Tactical Boots with Side Zipper
Gender: Men's
Color: Black
Price: $121.56MSRP: $152.0020% OFF
Rating

Vans - Mte™ Crosspath Mid. Color Lilac Grey. On sale for $125.95. MSRP $140.00. 10% off.

Gray Vans Mte™ Crosspath Mid

Gray Vans Mte™ Crosspath Mid

Brand Name: Vans
Product Name: Mte™ Crosspath Mid
Gender: Unisex
Color: Lilac Grey
Price: $125.95MSRP: $140.0010% OFF
Rating

Frye - Connor Venetian. Color Driftwood. On sale for $90.03. MSRP $158.00. 43% off. 4.0 out of 5 stars

Brown Frye Connor Venetian

Brown Frye Connor Venetian

+5

Brand Name: Frye
Product Name: Connor Venetian
Gender: Men's
Color: Driftwood
Price: $90.03MSRP: $158.0043% OFF
Rating: 4Rated 4 stars out of 5(1)

Ariat - Recon Lace Boots. Color Natural Suede. On sale for $121.56. MSRP $159.95. 24% off.

Tan Ariat Recon Lace Boots

Tan Ariat Recon Lace Boots

Brand Name: Ariat
Product Name: Recon Lace Boots
Gender: Men's
Color: Natural Suede
Price: $121.56MSRP: $159.9524% OFF
Rating

Stacy Adams - Madison (Cap Toe). Color Black. Low Stock. On sale for $109.15. MSRP $129.95. 16% off. 4.6 out of 5 stars

Low 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: $109.15MSRP: $129.9516% OFF
Rating: 5Rated 5 stars out of 5(821)

Marc Joseph New York - Chambers St. Color Whiskey Brushed Napa. Low Stock. On sale for $154.05. MSRP $195.00. 21% off.

Low Stock

Brown Marc Joseph New York Chambers St

Brown Marc Joseph New York Chambers St

+2

Brand Name: Marc Joseph New York
Product Name: Chambers St
Gender: Men's
Color: Whiskey Brushed Napa
Price: $154.05MSRP: $195.0021% OFF
Rating

Steve Madden - Possess. Color Black. On sale for $109.95. MSRP $120.00. 8% off. 3.0 out of 5 stars

Black Steve Madden Possess

Black Steve Madden Possess

+6

Brand Name: Steve Madden
Product Name: Possess
Gender: Men's
Color: Black
Price: $109.95MSRP: $120.008% OFF
Rating: 3Rated 3 stars out of 5(2)

Stacy Adams - Calandro City Sandal. Color Cognac. On sale for $78.82. MSRP $90.00. 12% off.

Tan Stacy Adams Calandro City Sandal

Tan Stacy Adams Calandro City Sandal

+3

Brand Name: Stacy Adams
Product Name: Calandro City Sandal
Gender: Men's
Color: Cognac
Price: $78.82MSRP: $90.0012% OFF
Rating

Frye - Astor Low Lace Court. Color Bluestone. On sale for $135.83. MSRP $158.00. 14% off. 5.0 out of 5 stars

Blue Frye Astor Low Lace Court

Blue Frye Astor Low Lace Court

+2

Brand Name: Frye
Product Name: Astor Low Lace Court
Gender: Men's
Color: Bluestone
Price: $135.83MSRP: $158.0014% OFF
Rating: 5Rated 5 stars out of 5(1)

Stacy Adams - Valet Velour Slip-On Loafer. Color Black. On sale for $62.95. MSRP $85.00. 26% off. 4.5 out of 5 stars

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: $62.95MSRP: $85.0026% OFF
Rating: 5Rated 5 stars out of 5(110)

Tommy Hilfiger - Rosell. Color Medium Brown. On sale for $72.76. MSRP $79.95. 9% off.

Brown Tommy Hilfiger Rosell

Brown Tommy Hilfiger Rosell

+1

Brand Name: Tommy Hilfiger
Product Name: Rosell
Gender: Men's
Color: Medium Brown
Price: $72.76MSRP: $79.959% OFF
Rating

Dan Post - Milwaukee. Color Black. On sale for $159.96. MSRP $199.95. 20% off. 3.8 out of 5 stars

Black Dan Post Milwaukee

Black Dan Post Milwaukee

Brand Name: Dan Post
Product Name: Milwaukee
Gender: Men's
Color: Black
Price: $159.96MSRP: $199.9520% OFF
Rating: 4Rated 4 stars out of 5(13)

Marc Joseph New York - Ovington. Color Whiskey Burnished Napa. On sale for $108.50. MSRP $155.00. 30% off. 5.0 out of 5 stars

Brown Marc Joseph New York Ovington

Brown Marc Joseph New York Ovington

Brand Name: Marc Joseph New York
Product Name: Ovington
Gender: Men's
Color: Whiskey Burnished Napa
Price: $108.50MSRP: $155.0030% OFF
Rating: 5Rated 5 stars out of 5(1)

Marc Joseph New York - Spring Street. Color Cognac Basket Napa. On sale for $131.25. MSRP $175.00. 25% off.

Brown Marc Joseph New York Spring Street

Brown Marc Joseph New York Spring Street

+2

Brand Name: Marc Joseph New York
Product Name: Spring Street
Gender: Men's
Color: Cognac Basket Napa
Price: $131.25MSRP: $175.0025% OFF
Rating

Nunn Bush - MAC Moccasin Toe Oxford. Color Black. On sale for $79.06. MSRP $100.00. 21% off. 5.0 out of 5 stars

Black Nunn Bush MAC Moccasin Toe Oxford

Black Nunn Bush MAC Moccasin Toe Oxford

Brand Name: Nunn Bush
Product Name: MAC Moccasin Toe Oxford
Gender: Men's
Color: Black
Price: $79.06MSRP: $100.0021% OFF
Rating: 5Rated 5 stars out of 5(4)

Johnston & Murphy - Bradford Dress Moc Oxford. Color Black Brush-Off. $128.95. 3.9 out of 5 stars

Black Johnston & Murphy Bradford Dress Moc Oxford

Black Johnston & Murphy Bradford Dress Moc Oxford

Brand Name: Johnston & Murphy
Product Name: Bradford Dress Moc Oxford
Gender: Men's
Color: Black Brush-Off
Price: $128.95
Rating: 4Rated 4 stars out of 5(16)

Tommy Hilfiger - Hines. Color White. On sale for $69.30. MSRP $99.00. 30% off.

White Tommy Hilfiger Hines

White Tommy Hilfiger Hines

+2

Brand Name: Tommy Hilfiger
Product Name: Hines
Gender: Men's
Color: White
Price: $69.30MSRP: $99.0030% OFF
Rating

Anthony Veer - Filmore Bit Loafer. Color Walnut. Low Stock. On sale for $109.97. MSRP $164.95. 33% off. 4.0 out of 5 stars

Low Stock

Brown Anthony Veer Filmore Bit Loafer

Brown Anthony Veer Filmore Bit Loafer

+3

Brand Name: Anthony Veer
Product Name: Filmore Bit Loafer
Gender: Men's
Color: Walnut
Price: $109.97MSRP: $164.9533% OFF
Rating: 4Rated 4 stars out of 5(81)

Anthony Veer - Clinton Tux. Color Black. Low Stock. On sale for $131.06. MSRP $199.95. 34% off. 5.0 out of 5 stars

Low Stock

Black Anthony Veer Clinton Tux

Black Anthony Veer Clinton Tux

Brand Name: Anthony Veer
Product Name: Clinton Tux
Gender: Men's
Color: Black
Price: $131.06MSRP: $199.9534% OFF
Rating: 5Rated 5 stars out of 5(70)

Join Our List, Get 10% Off

Sign up for Zappos emails—new subscribers get 10% off a future order!* Plus, get early access to sales, coupons, and more. (One code per email address.)