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

Size 8.5 Leather Outsole Leather Round Toe Products

48 items found

Sort By

Your Selections

Search Results

Cole Haan - Pinch Weekender Venetians. Color Black/Angora. $130.00.

Black Cole Haan Pinch Weekender Venetians

Black Cole Haan Pinch Weekender Venetians

+4

Brand Name: Cole Haan
Product Name: Pinch Weekender Venetians
Gender: Men's
Color: Black/Angora
Price: $130.00
Rating

Vans - MTE Ultrarange 2.0 RW. Color Black/Black. $100.00. 1.0 out of 5 stars

Black Vans MTE Ultrarange 2.0 RW

Black Vans MTE Ultrarange 2.0 RW

+10

Brand Name: Vans
Product Name: MTE Ultrarange 2.0 RW
Gender: Unisex
Color: Black/Black
Price: $100.00
Rating: 1Rated 1 star out of 5(1)

Johnston & Murphy - Hayes Penny Loafer. Color Burgundy. On sale for $99.90. MSRP $135.00. 26% off. 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: $99.90MSRP: $135.0026% OFF
Rating: 4Rated 4 stars out of 5(116)

Cole Haan - Grand+ Knit Oxfords. Color Navy Blazer/British Tan. On sale for $99.00. MSRP $110.00. 10% off.

Navy Cole Haan Grand+ Knit Oxfords

Navy Cole Haan Grand+ Knit Oxfords

Brand Name: Cole Haan
Product Name: Grand+ Knit Oxfords
Gender: Men's
Color: Navy Blazer/British Tan
Price: $99.00MSRP: $110.0010% OFF
Rating

Johnston & Murphy - Melton Classic Dress Cap Toe Oxford. Color Tan Italian Calfskin. $184.95. 4.3 out of 5 stars

Tan Johnston & Murphy Melton Classic Dress Cap Toe Oxford

Tan Johnston & Murphy Melton Classic Dress Cap Toe Oxford

+2

Brand Name: Johnston & Murphy
Product Name: Melton Classic Dress Cap Toe Oxford
Gender: Men's
Color: Tan Italian Calfskin
Price: $184.95
Rating: 4Rated 4 stars out of 5(1195)

Cole Haan - Grand Crosscourt Modern Perforated Lace To Toe Sneakers. Color Black/Ivory. On sale for $86.05. MSRP $110.00. 22% 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: $86.05MSRP: $110.0022% OFF
Rating: 5Rated 5 stars out of 5(1)

GFORE - Men's MG4+ TPU Golf Shoes. Color Twilight. $195.00. 1.0 out of 5 stars

Blue GFORE Men's MG4+ TPU Golf Shoes

Blue GFORE Men's MG4+ TPU Golf Shoes

+2

Brand Name: GFORE
Product Name: Men's MG4+ TPU Golf Shoes
Gender: Men's
Color: Twilight
Price: $195.00
Rating: 1Rated 1 star out of 5(1)

Cole Haan - Grand Crosscourt Modern Runner. Color Microchip/Quiet Shade/Optic White. $110.00.

Gray Cole Haan Grand Crosscourt Modern Runner

Gray Cole Haan Grand Crosscourt Modern Runner

+1

Brand Name: Cole Haan
Product Name: Grand Crosscourt Modern Runner
Gender: Men's
Color: Microchip/Quiet Shade/Optic White
Price: $110.00
Rating

Vans - Lowland 2.0. Color Heritage Blue. On sale for $76.45. MSRP $85.00. 10% off.

Navy Vans Lowland 2.0

Navy Vans Lowland 2.0

+2

Brand Name: Vans
Product Name: Lowland 2.0
Gender: Unisex
Color: Heritage Blue
Price: $76.45MSRP: $85.0010% OFF
Rating

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

Black Johnston & Murphy Hayes Tassel Loafer

Black Johnston & Murphy Hayes Tassel Loafer

+2 colors/patterns

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

Cole Haan - Og Energyweave Wingtip Oxfords. Color Golden Toffee Nubuck/China Blue/Ivory. $170.00.

Brown Cole Haan Og Energyweave Wingtip Oxfords

Brown Cole Haan Og Energyweave Wingtip Oxfords

Brand Name: Cole Haan
Product Name: Og Energyweave Wingtip Oxfords
Gender: Men's
Color: Golden Toffee Nubuck/China Blue/Ivory
Price: $170.00
Rating

Cole Haan - Grand Hurrion Stitchlite Plain Toe Oxfords. Color Black/Nimbus/Cloud Ivory. $130.00.

Black Cole Haan Grand Hurrion Stitchlite Plain Toe Oxfords

Black Cole Haan Grand Hurrion Stitchlite Plain Toe Oxfords

+2

Brand Name: Cole Haan
Product Name: Grand Hurrion Stitchlite Plain Toe Oxfords
Gender: Men's
Color: Black/Nimbus/Cloud Ivory
Price: $130.00
Rating

Marc Joseph New York - BROADWAY. Color Taupe Grainy Nobuck. On sale for $89.95. MSRP $165.00. 45% off.

Taupe Marc Joseph New York BROADWAY

Taupe Marc Joseph New York BROADWAY

+6

Brand Name: Marc Joseph New York
Product Name: BROADWAY
Gender: Men's
Color: Taupe Grainy Nobuck
Price: $89.95MSRP: $165.0045% OFF
Rating

Frye - Astor Low Lace Court. Color Fog. $157.95. 5.0 out of 5 stars

Gray Frye Astor Low Lace Court

Gray Frye Astor Low Lace Court

+2

Brand Name: Frye
Product Name: Astor Low Lace Court
Gender: Men's
Color: Fog
Price: $157.95
Rating: 5Rated 5 stars out of 5(1)

Vans - FU MTE Ultrarange EXO SE. Color Lavender Fog. On sale for $74.96. MSRP $100.00. 25% off. 2.7 out of 5 stars

Purple Vans FU MTE Ultrarange EXO SE

Purple Vans FU MTE Ultrarange EXO SE

Brand Name: Vans
Product Name: FU MTE Ultrarange EXO SE
Gender: Women's
Color: Lavender Fog
Price: $74.96MSRP: $100.0025% OFF
Rating: 3Rated 3 stars out of 5(12)

Johnston & Murphy Collection - Baldwin Leather Bit. Color Brown American Full Grain. $195.00. 3.9 out of 5 stars

Brown Johnston & Murphy Collection Baldwin Leather Bit

Brown Johnston & Murphy Collection Baldwin Leather Bit

Brand Name: Johnston & Murphy Collection
Product Name: Baldwin Leather Bit
Gender: Men's
Color: Brown American Full Grain
Price: $195.00
Rating: 4Rated 4 stars out of 5(14)

Cole Haan - Grand Crosscourt Sneakers. Color Light Sesame Nubuck/Ivory. $110.00.

Taupe Cole Haan Grand Crosscourt Sneakers

Taupe Cole Haan Grand Crosscourt Sneakers

Brand Name: Cole Haan
Product Name: Grand Crosscourt Sneakers
Gender: Men's
Color: Light Sesame Nubuck/Ivory
Price: $110.00
Rating

Frye - Connor Venetian. Color Black. On sale for $102.66. MSRP $158.00. 35% off. 4.0 out of 5 stars

Black Frye Connor Venetian

Black Frye Connor Venetian

+5

Brand Name: Frye
Product Name: Connor Venetian
Gender: Men's
Color: Black
Price: $102.66MSRP: $158.0035% OFF
Rating: 4Rated 4 stars out of 5(1)

Cole Haan - Grand Remix Knit Oxfords. Color Silver Lining/Acorn/Ivory. On sale for $99.00. MSRP $110.00. 10% off.

Beige Cole Haan Grand Remix Knit Oxfords

Beige Cole Haan Grand Remix Knit Oxfords

Brand Name: Cole Haan
Product Name: Grand Remix Knit Oxfords
Gender: Men's
Color: Silver Lining/Acorn/Ivory
Price: $99.00MSRP: $110.0010% OFF
Rating

Clarks - Un Kendric Way. Color Mahogany Leather. $160.00. 3.0 out of 5 stars

Mahogany Clarks Un Kendric Way

Mahogany Clarks Un Kendric Way

+2

Brand Name: Clarks
Product Name: Un Kendric Way
Gender: Men's
Color: Mahogany Leather
Price: $160.00
Rating: 3Rated 3 stars out of 5(2)

Cole Haan - Grandpro Featherarc Bike Toe Sneakers. Color Big Dipper/Sea Stone/Ivory. On sale for $135.00. MSRP $150.00. 10% off.

Navy Cole Haan Grandpro Featherarc Bike Toe Sneakers

Navy Cole Haan Grandpro Featherarc Bike Toe Sneakers

+2

Brand Name: Cole Haan
Product Name: Grandpro Featherarc Bike Toe Sneakers
Gender: Men's
Color: Big Dipper/Sea Stone/Ivory
Price: $135.00MSRP: $150.0010% OFF
Rating

Johnston & Murphy - Bradford Dress Moc Oxford. Color Black Brush-Off. $129.85. 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: $129.85
Rating: 4Rated 4 stars out of 5(16)

Florsheim - Berkley Penny Loafer. Color Burgundy. On sale for $124.99. MSRP $145.00. 14% off. 4.1 out of 5 stars

Burgundy Florsheim Berkley Penny Loafer

Burgundy Florsheim Berkley Penny Loafer

+2

Brand Name: Florsheim
Product Name: Berkley Penny Loafer
Gender: Men's
Color: Burgundy
Price: $124.99MSRP: $145.0014% OFF
Rating: 4Rated 4 stars out of 5(1324)

Cole Haan - Grandpro Ashland 2 Golf. Color Optic White/Glacier Gray/Ivory. On sale for $130.00. MSRP $160.00. 19% off.

White Cole Haan Grandpro Ashland 2 Golf

White Cole Haan Grandpro Ashland 2 Golf

+3

Brand Name: Cole Haan
Product Name: Grandpro Ashland 2 Golf
Gender: Men's
Color: Optic White/Glacier Gray/Ivory
Price: $130.00MSRP: $160.0019% OFF
Rating

Marc Joseph New York - Morrisville. Color Black Napa. On sale for $89.95. MSRP $185.00. 51% off. 5.0 out of 5 stars

Black Marc Joseph New York Morrisville

Black Marc Joseph New York Morrisville

+3

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

Marc Joseph New York - Ovington. Color Whiskey Burnished Napa. $155.00. 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: $155.00
Rating: 5Rated 5 stars out of 5(1)

Cole Haan - Grandpro Breakaway. Color Light Sesame Suede/Hickory/Medium Gum. $130.00. 1.0 out of 5 stars

Bone Cole Haan Grandpro Breakaway

Bone Cole Haan Grandpro Breakaway

Brand Name: Cole Haan
Product Name: Grandpro Breakaway
Gender: Men's
Color: Light Sesame Suede/Hickory/Medium Gum
Price: $130.00
Rating: 1Rated 1 star out of 5(1)

Cole Haan - American Classics Montrose Plain Toe Ox. Color Titanium Nubuck/Angora. On sale for $142.50. MSRP $190.00. 25% off.

Gray Cole Haan American Classics Montrose Plain Toe Ox

Gray Cole Haan American Classics Montrose Plain Toe Ox

+3

Brand Name: Cole Haan
Product Name: American Classics Montrose Plain Toe Ox
Gender: Men's
Color: Titanium Nubuck/Angora
Price: $142.50MSRP: $190.0025% OFF
Rating

Orthofeet - Pacific Palisades. Color White. On sale for $99.99. MSRP $149.95. 33% 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: $99.99MSRP: $149.9533% OFF
Rating: 4Rated 4 stars out of 5(2)

PUMA Golf - Royale. Color Warm White/Icy Blue. $159.99.

White PUMA Golf Royale

White PUMA Golf Royale

+2 colors/patterns

Brand Name: PUMA Golf
Product Name: Royale
Gender: Men's
Color: Warm White/Icy Blue
Price: $159.99
Rating

Florsheim - Lexington Wingtip Tassel Slip-On. Color Black. On sale for $129.95. MSRP $145.00. 10% off. 4.3 out of 5 stars

Black Florsheim Lexington Wingtip Tassel Slip-On

Black Florsheim Lexington Wingtip Tassel Slip-On

Brand Name: Florsheim
Product Name: Lexington Wingtip Tassel Slip-On
Gender: Men's
Color: Black
Price: $129.95MSRP: $145.0010% OFF
Rating: 4Rated 4 stars out of 5(483)

Stacy Adams - Madison (Cap Toe). Color Black. Low Stock. On sale for $121.53. MSRP $145.00. 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: $121.53MSRP: $145.0016% OFF
Rating: 5Rated 5 stars out of 5(822)

Florsheim - Como Imperial Slip-On Loafer. Color Black Cabaret. On sale for $129.95. MSRP $210.00. 38% 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: $210.0038% OFF
Rating: 4Rated 4 stars out of 5(495)

Tommy Hilfiger - Rezz6. Color Black. $89.00.

Black Tommy Hilfiger Rezz6

Black Tommy Hilfiger Rezz6

Brand Name: Tommy Hilfiger
Product Name: Rezz6
Gender: Men's
Color: Black
Price: $89.00
Rating

Volcom - Street Shield 8" Tactical Boots with Side Zipper. Color Black. On sale for $106.36. MSRP $152.00. 30% 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: $106.36MSRP: $152.0030% OFF
Rating

Ariat - Rebar Wedge Pull-On Waterproof Composite Toe Work Boots. Color Distressed Brown. On sale for $199.95. MSRP $209.95. 5% off. 4.1 out of 5 stars

Brown Ariat Rebar Wedge Pull-On Waterproof Composite Toe Work Boots

Brown Ariat Rebar Wedge Pull-On Waterproof Composite Toe Work Boots

Brand Name: Ariat
Product Name: Rebar Wedge Pull-On Waterproof Composite Toe Work Boots
Gender: Men's
Color: Distressed Brown
Price: $199.95MSRP: $209.955% OFF
Rating: 4Rated 4 stars out of 5(19)

Florsheim - Como Slip-On Loafer. Color Black. On sale for $129.95. MSRP $145.00. 10% off. 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: $129.95MSRP: $145.0010% OFF
Rating: 4Rated 4 stars out of 5(531)

Polo Ralph Lauren - Merton Vnetn. Color Tan. $168.00.

Tan Polo Ralph Lauren Merton Vnetn

Tan Polo Ralph Lauren Merton Vnetn

Brand Name: Polo Ralph Lauren
Product Name: Merton Vnetn
Gender: Men's
Color: Tan
Price: $168.00
Rating

Johnston & Murphy - Jenkins Plain Toe. Color Brown Leather. $99.90.

Brown Johnston & Murphy Jenkins Plain Toe

Brown Johnston & Murphy Jenkins Plain Toe

Brand Name: Johnston & Murphy
Product Name: Jenkins Plain Toe
Gender: Men's
Color: Brown Leather
Price: $99.90
Rating

Ariat - Longview Shock Shield 8" Waterproof Work Boots. Color Copper Brown. On sale for $189.95. MSRP $199.95. 5% off.

Brown Ariat Longview Shock Shield 8" Waterproof Work Boots

Brown Ariat Longview Shock Shield 8" Waterproof Work Boots

Brand Name: Ariat
Product Name: Longview Shock Shield 8" Waterproof Work Boots
Gender: Men's
Color: Copper Brown
Price: $189.95MSRP: $199.955% OFF
Rating

Ariat - Rebar Flex SD Composite Toe Work Boots. Color Distressed Brown/Stone. On sale for $199.95. MSRP $209.95. 5% off.

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: $199.95MSRP: $209.955% OFF
Rating

Ariat - Longview Shock Shield 8" Waterproof Composite Toe Work Boots. Color Copper Brown. On sale for $199.95. MSRP $209.95. 5% off.

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: $199.95MSRP: $209.955% OFF
Rating

Cole Haan - Grandpro Luxe Wholecut Sneakers. Color Optic White/Optic White. $180.00.

White Cole Haan Grandpro Luxe Wholecut Sneakers

White Cole Haan Grandpro Luxe Wholecut Sneakers

Brand Name: Cole Haan
Product Name: Grandpro Luxe Wholecut Sneakers
Gender: Men's
Color: Optic White/Optic White
Price: $180.00
Rating

Cole Haan - Grandpro Luxe Slip-On Sneakers. Color Golden Toffee Suede/Light Sesame/Ivory. $159.95. 3.2 out of 5 stars

Brown Cole Haan Grandpro Luxe Slip-On Sneakers

Brown Cole Haan Grandpro Luxe Slip-On Sneakers

+6

Brand Name: Cole Haan
Product Name: Grandpro Luxe Slip-On Sneakers
Gender: Men's
Color: Golden Toffee Suede/Light Sesame/Ivory
Price: $159.95
Rating: 3Rated 3 stars out of 5(4)

Anthony Veer - Filmore Bit Loafer. Color Walnut. Low Stock. On sale for $107.69. MSRP $164.95. 35% 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: $107.69MSRP: $164.9535% OFF
Rating: 4Rated 4 stars out of 5(81)

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

+15

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(6085)

Cole Haan - Original Grand 2.0. Color Big Dipper Nubuck/Ancient Scroll. On sale for $199.95. MSRP $230.00. 13% off.

Blue Cole Haan Original Grand 2.0

Blue Cole Haan Original Grand 2.0

+2

Brand Name: Cole Haan
Product Name: Original Grand 2.0
Gender: Men's
Color: Big Dipper Nubuck/Ancient Scroll
Price: $199.95MSRP: $230.0013% OFF
Rating

Nunn Bush - MAC Moccasin Toe Oxford. Color Black. On sale for $80.00. MSRP $100.00. 20% 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: $80.00MSRP: $100.0020% OFF
Rating: 5Rated 5 stars out of 5(4)

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.)