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

Size 8.5 Leather Winter Shoes

33 items found

Sort By

Your Selections

Search Results

Cole Haan - Originalgrand Shortwing Oxford. Color Woodbury Leather/Ivory. $149.95. 4.5 out of 5 stars

Burgundy Cole Haan Originalgrand Shortwing Oxford

Burgundy Cole Haan Originalgrand Shortwing Oxford

+5

Brand Name: Cole Haan
Product Name: Originalgrand Shortwing Oxford
Gender: Men's
Color: Woodbury Leather/Ivory
Price: $149.95
Rating: 4Rated 4 stars out of 5(1122)

Stacy Adams - Maddox Cap Toe Oxford. Color Chocolate. On sale for $89.95. MSRP $114.95.. 4.3 out of 5 stars

Brown Stacy Adams Maddox Cap Toe Oxford

Brown Stacy Adams Maddox Cap Toe Oxford

+1

Brand Name: Stacy Adams
Product Name: Maddox Cap Toe Oxford
Gender: Men's
Color: Chocolate
Price: $89.95MSRP: $114.95
Rating: 4Rated 4 stars out of 5(56)

Cole Haan - 2.Zerogrand Wing Oxford. Color Irish Coffee/Turbulence. Low Stock. On sale for $104.40. MSRP $180.00.. 4.8 out of 5 stars

7 left in stock

Brown Cole Haan 2.Zerogrand Wing Oxford

Brown Cole Haan 2.Zerogrand Wing Oxford

+4

Brand Name: Cole Haan
Product Name: 2.Zerogrand Wing Oxford
Gender: Men's
Color: Irish Coffee/Turbulence
Price: $104.40MSRP: $180.00
Rating: 5Rated 5 stars out of 5(20)

Clarks - Wallabee. Color Maple Suede. $160.00. 4.8 out of 5 stars

Brown Clarks Wallabee

Brown Clarks Wallabee

+4

Brand Name: Clarks
Product Name: Wallabee
Gender: Men's
Color: Maple Suede
Price: $160.00
Rating: 5Rated 5 stars out of 5(205)

Eastland 1955 Edition - Yarmouth. Color Oak. On sale for $74.95. MSRP $110.00.. 3.5 out of 5 stars

Brown Eastland 1955 Edition Yarmouth

Brown Eastland 1955 Edition Yarmouth

Brand Name: Eastland 1955 Edition
Product Name: Yarmouth
Gender: Men's
Color: Oak
Price: $74.95MSRP: $110.00
Rating: 4Rated 4 stars out of 5(2)

Florsheim - Rucci Wing Tip Oxford. Color Cognac Smooth. $129.95. 4.5 out of 5 stars

Neutral Florsheim Rucci Wing Tip Oxford

Neutral Florsheim Rucci Wing Tip Oxford

+2

Brand Name: Florsheim
Product Name: Rucci Wing Tip Oxford
Gender: Men's
Color: Cognac Smooth
Price: $129.95
Rating: 5Rated 5 stars out of 5(61)

Polo Ralph Lauren - Riali Loafer. Color Black Heavyweight Smooth Leather. $128.00. 4.4 out of 5 stars

Black Polo Ralph Lauren Riali Loafer

Black Polo Ralph Lauren Riali Loafer

+3

Brand Name: Polo Ralph Lauren
Product Name: Riali Loafer
Gender: Men's
Color: Black Heavyweight Smooth Leather
Price: $128.00
Rating: 4Rated 4 stars out of 5(12)

Deer Stags - Times Comfort Oxford. Color Brown 2. On sale for $51.69. MSRP $57.99.. 4.0 out of 5 stars

Brown Deer Stags Times Comfort Oxford

Brown Deer Stags Times Comfort Oxford

+2

Brand Name: Deer Stags
Product Name: Times Comfort Oxford
Gender: Men's
Color: Brown 2
Price: $51.69MSRP: $57.99
Rating: 4Rated 4 stars out of 5(696)

Glerups - Wool Shoe Leather Outsole. Color Charcoal. On sale for $100.60. MSRP $105.00.. 4.7 out of 5 stars

Gray Glerups Wool Shoe Leather Outsole

Gray Glerups Wool Shoe Leather Outsole

+7

Brand Name: Glerups
Product Name: Wool Shoe Leather Outsole
Gender: Unisex
Color: Charcoal
Price: $100.60MSRP: $105.00
Rating: 5Rated 5 stars out of 5(320)

UGG - City Butte. Color Dune 1. On sale for $87.38. MSRP $189.95.. 4.1 out of 5 stars

Khaki UGG City Butte

Khaki UGG City Butte

+3

Brand Name: UGG
Product Name: City Butte
Gender: Men's
Color: Dune 1
Price: $87.38MSRP: $189.95
Rating: 4Rated 4 stars out of 5(12)

Johnston & Murphy - Holden Embossed Wing Tip. Color Brown. $129.00. 3.8 out of 5 stars

Brown Johnston & Murphy Holden Embossed Wing Tip

Brown Johnston & Murphy Holden Embossed Wing Tip

Brand Name: Johnston & Murphy
Product Name: Holden Embossed Wing Tip
Gender: Men's
Color: Brown
Price: $129.00
Rating: 4Rated 4 stars out of 5(29)

SOREL - Carson™ Moc Waterproof. Color Major/Wet Sand. On sale for $98.92. MSRP $165.00.. 4.3 out of 5 stars

Brown SOREL Carson™ Moc Waterproof

Brown SOREL Carson™ Moc Waterproof

+2

Brand Name: SOREL
Product Name: Carson™ Moc Waterproof
Gender: Men's
Color: Major/Wet Sand
Price: $98.92MSRP: $165.00
Rating: 4Rated 4 stars out of 5(36)

Florsheim - Lodge Moc Toe Oxford. Color Brown Crazy Horse. $114.95. 4.5 out of 5 stars

Brown Florsheim Lodge Moc Toe Oxford

Brown Florsheim Lodge Moc Toe Oxford

Brand Name: Florsheim
Product Name: Lodge Moc Toe Oxford
Gender: Men's
Color: Brown Crazy Horse
Price: $114.95
Rating: 5Rated 5 stars out of 5(27)

Eastland 1955 Edition - Yarmouth. Color Bomber Brown Leather. On sale for $99.95. MSRP $110.00.. 5.0 out of 5 stars

Brown Eastland 1955 Edition Yarmouth

Brown Eastland 1955 Edition Yarmouth

+2 colors/patterns

Brand Name: Eastland 1955 Edition
Product Name: Yarmouth
Gender: Men's
Color: Bomber Brown Leather
Price: $99.95MSRP: $110.00
Rating: 5Rated 5 stars out of 5(2)

Sperry - Davenport Penny. Color Black 1. $109.95. 3.7 out of 5 stars

Black Sperry Davenport Penny

Black Sperry Davenport Penny

Brand Name: Sperry
Product Name: Davenport Penny
Gender: Men's
Color: Black 1
Price: $109.95
Rating: 4Rated 4 stars out of 5(46)

Propet - Blizzard Tall Zip. Color Brown/Black. $134.95. 4.6 out of 5 stars

Brown Propet Blizzard Tall Zip

Brown Propet Blizzard Tall Zip

Brand Name: Propet
Product Name: Blizzard Tall Zip
Gender: Men's
Color: Brown/Black
Price: $134.95
Rating: 5Rated 5 stars out of 5(10)

KEEN - Circadia Mid Polar. Color Black/Steel Grey. On sale for $108.65. MSRP $145.00.. 4.0 out of 5 stars

Black KEEN Circadia Mid Polar

Black KEEN Circadia Mid Polar

+2 colors/patterns

Brand Name: KEEN
Product Name: Circadia Mid Polar
Gender: Men's
Color: Black/Steel Grey
Price: $108.65MSRP: $145.00
Rating: 4Rated 4 stars out of 5(3)

Anthony Veer - Clinton Tux. Color Black. $199.95. 5.0 out of 5 stars

Black Anthony Veer Clinton Tux

Black Anthony Veer Clinton Tux

Brand Name: Anthony Veer
Product Name: Clinton Tux
Gender: Men's
Color: Black
Price: $199.95
Rating: 5Rated 5 stars out of 5(2)

Helly Hansen - Garibaldi V3. Color New Wheat/Black/Soccer Gum. Low Stock. On sale for $96.00. MSRP $160.00.. 3.9 out of 5 stars

7 left in stock

Taupe Helly Hansen Garibaldi V3

Taupe Helly Hansen Garibaldi V3

+2

Brand Name: Helly Hansen
Product Name: Garibaldi V3
Gender: Men's
Color: New Wheat/Black/Soccer Gum
Price: $96.00MSRP: $160.00
Rating: 4Rated 4 stars out of 5(18)

Vans - Standard Mid MTE. Color Benny Urban Marshmallow/Burgundy. Low Stock. On sale for $77.97. MSRP $150.00.. 3.5 out of 5 stars

6 left in stock

White Vans Standard Mid MTE

White Vans Standard Mid MTE

+6

Brand Name: Vans
Product Name: Standard Mid MTE
Gender: Unisex
Color: Benny Urban Marshmallow/Burgundy
Price: $77.97MSRP: $150.00
Rating: 4Rated 4 stars out of 5(95)

Sperry - Avenue Duck Boot. Color Tan/Brown. $119.95. 4.1 out of 5 stars

Tan Sperry Avenue Duck Boot

Tan Sperry Avenue Duck Boot

+2

Brand Name: Sperry
Product Name: Avenue Duck Boot
Gender: Men's
Color: Tan/Brown
Price: $119.95
Rating: 4Rated 4 stars out of 5(215)

Columbia - Bugaboot™ Celsius Plus. Color Black/Graphite. On sale for $139.36. MSRP $170.00.. 4.6 out of 5 stars

Black Columbia Bugaboot™ Celsius Plus

Black Columbia Bugaboot™ Celsius Plus

+2

Brand Name: Columbia
Product Name: Bugaboot™ Celsius Plus
Gender: Men's
Color: Black/Graphite
Price: $139.36MSRP: $170.00
Rating: 5Rated 5 stars out of 5(39)

Vans - Standard MTE Snow Boot. Color Black/White 21. On sale for $139.35. MSRP $169.99.. 4.4 out of 5 stars

Black Vans Standard MTE Snow Boot

Black Vans Standard MTE Snow Boot

Brand Name: Vans
Product Name: Standard MTE Snow Boot
Gender: Men's
Color: Black/White 21
Price: $139.35MSRP: $169.99
Rating: 4Rated 4 stars out of 5(51)

Merrell - Coldpack 3 Thermo Tall Zip Waterproof. Color Black. $189.95. 4.2 out of 5 stars

Black Merrell Coldpack 3 Thermo Tall Zip Waterproof

Black Merrell Coldpack 3 Thermo Tall Zip Waterproof

Brand Name: Merrell
Product Name: Coldpack 3 Thermo Tall Zip Waterproof
Gender: Women's
Color: Black
Price: $189.95
Rating: 4Rated 4 stars out of 5(9)

Merrell - Coldpack 3 Thermo Mid Waterproof. Color Black. On sale for $159.99. MSRP $175.00.. 4.4 out of 5 stars

Black Merrell Coldpack 3 Thermo Mid Waterproof

Black Merrell Coldpack 3 Thermo Mid Waterproof

+2 colors/patterns

Brand Name: Merrell
Product Name: Coldpack 3 Thermo Mid Waterproof
Gender: Men's
Color: Black
Price: $159.99MSRP: $175.00
Rating: 4Rated 4 stars out of 5(25)

Sperry - Cold Bay. Color Black. $129.95. 4.5 out of 5 stars

Black Sperry Cold Bay

Black Sperry Cold Bay

Brand Name: Sperry
Product Name: Cold Bay
Gender: Men's
Color: Black
Price: $129.95
Rating: 5Rated 5 stars out of 5(136)

SALEWA - Alp Mate Winter Mid WP. Color Onyx/Black. Low Stock. $199.95. 5.0 out of 5 stars

5 left in stock

Black SALEWA Alp Mate Winter Mid WP

Black SALEWA Alp Mate Winter Mid WP

Brand Name: SALEWA
Product Name: Alp Mate Winter Mid WP
Gender: Men's
Color: Onyx/Black
Price: $199.95
Rating: 5Rated 5 stars out of 5(1)

Merrell - Moab 3 Thermo Mid WP. Color Earth. Low Stock. $159.95. 4.6 out of 5 stars

4 left in stock

Brown Merrell Moab 3 Thermo Mid WP

Brown Merrell Moab 3 Thermo Mid WP

Brand Name: Merrell
Product Name: Moab 3 Thermo Mid WP
Gender: Men's
Color: Earth
Price: $159.95
Rating: 5Rated 5 stars out of 5(140)

Baffin - Tavern. Color Brown. Low Stock. On sale for $143.50. MSRP $205.00..

6 left in stock

Brown Baffin Tavern

Brown Baffin Tavern

+2

Brand Name: Baffin
Product Name: Tavern
Gender: Men's
Color: Brown
Price: $143.50MSRP: $205.00
Rating

Columbia - Bugaboot III. Color Graphite/Black. Low Stock. $119.95. 4.3 out of 5 stars

4 left in stock

Gray Columbia Bugaboot III

Gray Columbia Bugaboot III

Brand Name: Columbia
Product Name: Bugaboot III
Gender: Men's
Color: Graphite/Black
Price: $119.95
Rating: 4Rated 4 stars out of 5(316)

KEEN - Revel 4 Mid Height Polar Insulated Waterproof. Color Black/Magnet. Low Stock. $179.95. 4.4 out of 5 stars

2 left in stock

Silver KEEN Revel 4 Mid Height Polar Insulated Waterproof

Silver KEEN Revel 4 Mid Height Polar Insulated Waterproof

Brand Name: KEEN
Product Name: Revel 4 Mid Height Polar Insulated Waterproof
Gender: Men's
Color: Black/Magnet
Price: $179.95
Rating: 4Rated 4 stars out of 5(14)

DC - Navigator. Color Black/Black/Black 1. Low Stock. On sale for $111.92. MSRP $125.00.. 2.0 out of 5 stars

3 left in stock

Black DC Navigator

Black DC Navigator

+2

Brand Name: DC
Product Name: Navigator
Gender: Men's
Color: Black/Black/Black 1
Price: $111.92MSRP: $125.00
Rating: 2Rated 2 stars out of 5(1)

Pajar CANADA - Fireburst. Color Black. Low Stock. On sale for $175.00. MSRP $195.00..

8 left in stock

Black Pajar CANADA Fireburst

Black Pajar CANADA Fireburst

Brand Name: Pajar CANADA
Product Name: Fireburst
Gender: Men's
Color: Black
Price: $175.00MSRP: $195.00
Rating

Get on the List

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