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

Size 8.5 Casual Winter Products

52 items found

Sort By

Your Selections

Search Results

Ariat - Cruiser. Color Teal Suede. $94.95. 4.6 out of 5 stars

Green Ariat Cruiser

Green Ariat Cruiser

+24

Brand Name: Ariat
Product Name: Cruiser
Color: Teal Suede
Price: $94.95
Rating: 5Rated 5 stars out of 5(1161)

SOREL - Out N About™ III Classic. Color Yellow Ray/Sea Salt. On sale for $97.50. MSRP $130.00.. 4.2 out of 5 stars

Yellow SOREL Out N About™ III Classic

Yellow SOREL Out N About™ III Classic

+8

Brand Name: SOREL
Product Name: Out N About™ III Classic
Color: Yellow Ray/Sea Salt
Price: $97.50MSRP: $130.00
Rating: 4Rated 4 stars out of 5(1193)

Roxy - Hail Ya Boots. Color Black. On sale for $112.34. MSRP $139.00..

Black Roxy Hail Ya Boots

Black Roxy Hail Ya Boots

Brand Name: Roxy
Product Name: Hail Ya Boots
Color: Black
Price: $112.34MSRP: $139.00
Rating

Propet - Demi. Color Indigo. On sale for $79.49. MSRP $109.95.. 4.0 out of 5 stars

Blue Propet Demi

Blue Propet Demi

+4

Brand Name: Propet
Product Name: Demi
Color: Indigo
Price: $79.49MSRP: $109.95
Rating: 4Rated 4 stars out of 5(4)

Helly Hansen - Beloved 2.0. Color Beluga. On sale for $118.50. MSRP $150.00..

Multi Helly Hansen Beloved 2.0

Multi Helly Hansen Beloved 2.0

+2

Brand Name: Helly Hansen
Product Name: Beloved 2.0
Color: Beluga
Price: $118.50MSRP: $150.00
Rating

Helly Hansen - Alma. Color New Wheat. On sale for $137.70. MSRP $170.00.. 5.0 out of 5 stars

Tan Helly Hansen Alma

Tan Helly Hansen Alma

+2

Brand Name: Helly Hansen
Product Name: Alma
Color: New Wheat
Price: $137.70MSRP: $170.00
Rating: 5Rated 5 stars out of 5(4)

Vans - Standard Mid V Snow MTE. Color Light Blue. On sale for $136.76. MSRP $190.00.. 5.0 out of 5 stars

Blue Vans Standard Mid V Snow MTE

Blue Vans Standard Mid V Snow MTE

Brand Name: Vans
Product Name: Standard Mid V Snow MTE
Color: Light Blue
Price: $136.76MSRP: $190.00
Rating: 5Rated 5 stars out of 5(1)

Lucky Brand - Hybiscus. Color Silver Cloud. On sale for $131.40. MSRP $219.00.. 4.2 out of 5 stars

+3

Brand Name: Lucky Brand
Product Name: Hybiscus
Color: Silver Cloud
Price: $131.40MSRP: $219.00
Rating: 4Rated 4 stars out of 5(25)

Carhartt - Pellston WP Ins. 8" Winter Boot. Color Light Brown Oil Nubuck. $184.99.

Brown Carhartt Pellston WP Ins. 8" Winter Boot

Brown Carhartt Pellston WP Ins. 8" Winter Boot

Brand Name: Carhartt
Product Name: Pellston WP Ins. 8" Winter Boot
Color: Light Brown Oil Nubuck
Price: $184.99
Rating

La Canadienne - Hunter. Color Black Leather. $585.00. 4.7 out of 5 stars

Black La Canadienne Hunter

Black La Canadienne Hunter

Brand Name: La Canadienne
Product Name: Hunter
Color: Black Leather
Price: $585.00
Rating: 5Rated 5 stars out of 5(24)

Carhartt - WP 8" Ins. Wedge Fold Down Winter Boot. Color Bison Brown Oil Tan. $179.99.

Brown Carhartt WP 8" Ins. Wedge Fold Down Winter Boot

Brown Carhartt WP 8" Ins. Wedge Fold Down Winter Boot

Brand Name: Carhartt
Product Name: WP 8" Ins. Wedge Fold Down Winter Boot
Color: Bison Brown Oil Tan
Price: $179.99
Rating

Carhartt - WP 8" Ins. Wedge Fold Down Winter Boot. Color Dark Grey Nubuck. On sale for $134.99. MSRP $179.99..

Brown Carhartt WP 8" Ins. Wedge Fold Down Winter Boot

Brown Carhartt WP 8" Ins. Wedge Fold Down Winter Boot

Brand Name: Carhartt
Product Name: WP 8" Ins. Wedge Fold Down Winter Boot
Color: Dark Grey Nubuck
Price: $134.99MSRP: $179.99
Rating

Vans - Standard™ Snow MTE™. Color Grey/Black. On sale for $106.17. MSRP $180.00.. 4.1 out of 5 stars

Gray Vans Standard™ Snow MTE™

Gray Vans Standard™ Snow MTE™

+2

Brand Name: Vans
Product Name: Standard™ Snow MTE™
Color: Grey/Black
Price: $106.17MSRP: $180.00
Rating: 4Rated 4 stars out of 5(9)

Roxy - Lorena II Boots. Color Black. $98.95. 5.0 out of 5 stars

Black Roxy Lorena II Boots

Black Roxy Lorena II Boots

+2

Brand Name: Roxy
Product Name: Lorena II Boots
Color: Black
Price: $98.95
Rating: 5Rated 5 stars out of 5(1)

Smartwool - Snowboard Targeted Cushion Extra Stretch Over the Calf. Color Moonbeam. On sale for $17.64. MSRP $28.00.. 4.2 out of 5 stars

Taupe Smartwool Snowboard Targeted Cushion Extra Stretch Over the Calf

Brand Name: Smartwool
Product Name: Snowboard Targeted Cushion Extra Stretch Over the Calf
Color: Moonbeam
Price: $17.64MSRP: $28.00
Rating: 4Rated 4 stars out of 5(4)

KEEN - Howser II. Color Andorra/Orange. On sale for $71.21. MSRP $95.00.. 4.4 out of 5 stars

Orange KEEN Howser II

Orange KEEN Howser II

+4

Brand Name: KEEN
Product Name: Howser II
Color: Andorra/Orange
Price: $71.21MSRP: $95.00
Rating: 4Rated 4 stars out of 5(203)

La Canadienne - Douglas. Color Bordo Leather. Low Stock. On sale for $165.75. MSRP $425.00.. 4.3 out of 5 stars

8 left in stock

Burgundy La Canadienne Douglas

Burgundy La Canadienne Douglas

Brand Name: La Canadienne
Product Name: Douglas
Color: Bordo Leather
Price: $165.75MSRP: $425.00
Rating: 4Rated 4 stars out of 5(6)

JBU - Free Bird. Color Gunmetal. On sale for $63.65. MSRP $74.50.. 3.4 out of 5 stars

Gray JBU Free Bird

Gray JBU Free Bird

+3

Brand Name: JBU
Product Name: Free Bird
Color: Gunmetal
Price: $63.65MSRP: $74.50
Rating: 3Rated 3 stars out of 5(5)

Frye - Veronica Harness Short. Color Caramel. Low Stock. On sale for $219.98. MSRP $298.00.. 3.6 out of 5 stars

4 left in stock

Brown Frye Veronica Harness Short

Brown Frye Veronica Harness Short

+1

Brand Name: Frye
Product Name: Veronica Harness Short
Color: Caramel
Price: $219.98MSRP: $298.00
Rating: 4Rated 4 stars out of 5(16)

Steve Madden - Pop Winter Boot. Color Black. On sale for $64.19. MSRP $99.95.. 3.4 out of 5 stars

Black Steve Madden Pop Winter Boot

Black Steve Madden Pop Winter Boot

+3

Brand Name: Steve Madden
Product Name: Pop Winter Boot
Color: Black
Price: $64.19MSRP: $99.95
Rating: 3Rated 3 stars out of 5(5)

Kamik - Rogue Hike 3. Color Cognac. Low Stock. On sale for $93.81. MSRP $120.00.. 4.3 out of 5 stars

2 left in stock

Tan Kamik Rogue Hike 3

Tan Kamik Rogue Hike 3

+3

Brand Name: Kamik
Product Name: Rogue Hike 3
Color: Cognac
Price: $93.81MSRP: $120.00
Rating: 4Rated 4 stars out of 5(3)

SOREL - Explorer™ II Carnival Cozy. Color Nova Sand/Chrome Grey. Low Stock. On sale for $134.81. MSRP $155.00.. 4.2 out of 5 stars

1 left in stock

Pink SOREL Explorer™ II Carnival Cozy

Pink SOREL Explorer™ II Carnival Cozy

+3

Brand Name: SOREL
Product Name: Explorer™ II Carnival Cozy
Color: Nova Sand/Chrome Grey
Price: $134.81MSRP: $155.00
Rating: 4Rated 4 stars out of 5(229)

Chaco - Ramble Puff Clog. Color Black. $74.95. 3.6 out of 5 stars

Black Chaco Ramble Puff Clog

Black Chaco Ramble Puff Clog

+2

Brand Name: Chaco
Product Name: Ramble Puff Clog
Color: Black
Price: $74.95
Rating: 4Rated 4 stars out of 5(10)

The North Face - Storm Strike III Waterproof. Color Deep Taupe/TNF Black. Low Stock. On sale for $91.90. MSRP $139.00.. 2.7 out of 5 stars

6 left in stock

Taupe The North Face Storm Strike III Waterproof

Taupe The North Face Storm Strike III Waterproof

Brand Name: The North Face
Product Name: Storm Strike III Waterproof
Color: Deep Taupe/TNF Black
Price: $91.90MSRP: $139.00
Rating: 3Rated 3 stars out of 5(3)

Falke - Cosyshoe. Color Almond Blossom. $71.00. 4.2 out of 5 stars

Pink Falke Cosyshoe

Pink Falke Cosyshoe

+4

Brand Name: Falke
Product Name: Cosyshoe
Color: Almond Blossom
Price: $71.00
Rating: 4Rated 4 stars out of 5(13)

Columbia - Moritza™ Shorty. Color Black/Kettle. On sale for $87.59. MSRP $110.00.. 4.6 out of 5 stars

Black Columbia Moritza™ Shorty

Black Columbia Moritza™ Shorty

Brand Name: Columbia
Product Name: Moritza™ Shorty
Color: Black/Kettle
Price: $87.59MSRP: $110.00
Rating: 5Rated 5 stars out of 5(55)

Alegria - Keli Professional. Color Plaid To Meet You. $130.00. 4.1 out of 5 stars

Black Alegria Keli Professional

Black Alegria Keli Professional

Brand Name: Alegria
Product Name: Keli Professional
Color: Plaid To Meet You
Price: $130.00
Rating: 4Rated 4 stars out of 5(566)

Alegria - Debra. Color Depth Perception. On sale for $97.50. MSRP $130.00.. 3.8 out of 5 stars

Black Alegria Debra

Black Alegria Debra

Brand Name: Alegria
Product Name: Debra
Color: Depth Perception
Price: $97.50MSRP: $130.00
Rating: 4Rated 4 stars out of 5(47)

LifeStride - Impact. Color Black Synthetic. On sale for $49.99. MSRP $79.99.. 3.9 out of 5 stars

Black LifeStride Impact

Black LifeStride Impact

Brand Name: LifeStride
Product Name: Impact
Color: Black Synthetic
Price: $49.99MSRP: $79.99
Rating: 4Rated 4 stars out of 5(79)

Sperry - Saltwater Alpine. Color White. On sale for $62.02. MSRP $110.00.. 4.2 out of 5 stars

White Sperry Saltwater Alpine

White Sperry Saltwater Alpine

+3

Brand Name: Sperry
Product Name: Saltwater Alpine
Color: White
Price: $62.02MSRP: $110.00
Rating: 4Rated 4 stars out of 5(120)

Dirty Laundry - Nirvana. Color White Chill Smooth. On sale for $57.06. MSRP $64.95.. 3.0 out of 5 stars

White Dirty Laundry Nirvana

White Dirty Laundry Nirvana

+2

Brand Name: Dirty Laundry
Product Name: Nirvana
Color: White Chill Smooth
Price: $57.06MSRP: $64.95
Rating: 3Rated 3 stars out of 5(3)

Arcopedico - Sec V. Color Denim. Low Stock. $68.95. 4.1 out of 5 stars

2 left in stock

Blue Arcopedico Sec V

Blue Arcopedico Sec V

Brand Name: Arcopedico
Product Name: Sec V
Color: Denim
Price: $68.95
Rating: 4Rated 4 stars out of 5(26)

Revitalign - Bella Orthotic Loafer. Color Black. Low Stock. $99.99. 3.9 out of 5 stars

10 left in stock

Black Revitalign Bella Orthotic Loafer

Black Revitalign Bella Orthotic Loafer

Brand Name: Revitalign
Product Name: Bella Orthotic Loafer
Color: Black
Price: $99.99
Rating: 4Rated 4 stars out of 5(8)

Sperry - Seaport Penny. Color New Tan. $105.00. 4.5 out of 5 stars

Tan Sperry Seaport Penny

Tan Sperry Seaport Penny

+5

Brand Name: Sperry
Product Name: Seaport Penny
Color: New Tan
Price: $105.00
Rating: 5Rated 5 stars out of 5(1127)

Naturalizer - Maxwell. Color English Tea. On sale for $79.95. MSRP $89.00.. 4.0 out of 5 stars

Orange Naturalizer Maxwell

Orange Naturalizer Maxwell

+15

Brand Name: Naturalizer
Product Name: Maxwell
Color: English Tea
Price: $79.95MSRP: $89.00
Rating: 4Rated 4 stars out of 5(428)

Eastland 1955 Edition - Patricia. Color Camel. On sale for $79.95. MSRP $100.00.. 3.6 out of 5 stars

Tan Eastland 1955 Edition Patricia

Tan Eastland 1955 Edition Patricia

+12

Brand Name: Eastland 1955 Edition
Product Name: Patricia
Color: Camel
Price: $79.95MSRP: $100.00
Rating: 4Rated 4 stars out of 5(100)

Eastland 1955 Edition - Sadie. Color Black/White. On sale for $84.95. MSRP $100.00.. 4.3 out of 5 stars

Black Eastland 1955 Edition Sadie

Black Eastland 1955 Edition Sadie

+4

Brand Name: Eastland 1955 Edition
Product Name: Sadie
Color: Black/White
Price: $84.95MSRP: $100.00
Rating: 4Rated 4 stars out of 5(29)

Acorn - Lightweight Bristol Loafer. Color Buff Popcorn. Low Stock. On sale for $42.92. MSRP $47.00.. 4.0 out of 5 stars

5 left in stock

White Acorn Lightweight Bristol Loafer

White Acorn Lightweight Bristol Loafer

+3

Brand Name: Acorn
Product Name: Lightweight Bristol Loafer
Color: Buff Popcorn
Price: $42.92MSRP: $47.00
Rating: 4Rated 4 stars out of 5(142)

Dansko - Kane. Color Black Molded. $84.95. 4.3 out of 5 stars

Black Dansko Kane

Black Dansko Kane

+3

Brand Name: Dansko
Product Name: Kane
Color: Black Molded
Price: $84.95
Rating: 4Rated 4 stars out of 5(296)

Glerups - Wool Shoe Leather Outsole. Color Charcoal. $104.95. 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
Color: Charcoal
Price: $104.95
Rating: 5Rated 5 stars out of 5(320)

Klogs Footwear - Moxy. Color Black Full Grain. $149.95. 4.0 out of 5 stars

Black Klogs Footwear Moxy

Black Klogs Footwear Moxy

Brand Name: Klogs Footwear
Product Name: Moxy
Color: Black Full Grain
Price: $149.95
Rating: 4Rated 4 stars out of 5(26)

Propet - Colbie. Color Black. $74.95. 3.2 out of 5 stars

Black Propet Colbie

Black Propet Colbie

+4

Brand Name: Propet
Product Name: Colbie
Color: Black
Price: $74.95
Rating: 3Rated 3 stars out of 5(77)

Aetrex - Libby. Color Brown. $139.90. 4.0 out of 5 stars

Brown Aetrex Libby

Brown Aetrex Libby

+2

Brand Name: Aetrex
Product Name: Libby
Color: Brown
Price: $139.90
Rating: 4Rated 4 stars out of 5(64)

LifeStride - Zee. Color Black 1. $69.94. 4.2 out of 5 stars

Black LifeStride Zee

Black LifeStride Zee

+3

Brand Name: LifeStride
Product Name: Zee
Color: Black 1
Price: $69.94
Rating: 4Rated 4 stars out of 5(181)

SoftWalk - Willis. Color Pewter Leather. On sale for $99.95. MSRP $119.95.. 3.7 out of 5 stars

Pewter SoftWalk Willis

Pewter SoftWalk Willis

+3

Brand Name: SoftWalk
Product Name: Willis
Color: Pewter Leather
Price: $99.95MSRP: $119.95
Rating: 4Rated 4 stars out of 5(277)

Acorn - Acorn Moc. Color Ewe Woven Tweed. $47.95. 4.2 out of 5 stars

Neutral Acorn Acorn Moc

Neutral Acorn Acorn Moc

+7

Brand Name: Acorn
Product Name: Acorn Moc
Color: Ewe Woven Tweed
Price: $47.95
Rating: 4Rated 4 stars out of 5(801)

LifeStride - Margot. Color Black Croc Synthetic. On sale for $49.99. MSRP $69.99.. 3.9 out of 5 stars

Black LifeStride Margot

Black LifeStride Margot

+3

Brand Name: LifeStride
Product Name: Margot
Color: Black Croc Synthetic
Price: $49.99MSRP: $69.99
Rating: 4Rated 4 stars out of 5(148)

Franco Sarto - Bocca. Color Navy Leather. $109.95. 4.2 out of 5 stars

Blue Franco Sarto Bocca

Blue Franco Sarto Bocca

Brand Name: Franco Sarto
Product Name: Bocca
Color: Navy Leather
Price: $109.95
Rating: 4Rated 4 stars out of 5(65)

Acorn - Moc Ragg. Color Dark Charcoal Ragg Wool. $46.95. 4.1 out of 5 stars

Gray Acorn Moc Ragg

Gray Acorn Moc Ragg

+2

Brand Name: Acorn
Product Name: Moc Ragg
Color: Dark Charcoal Ragg Wool
Price: $46.95
Rating: 4Rated 4 stars out of 5(176)

French Sole - Onstage. Color Black Patent/Black Suede. $195.00. 4.7 out of 5 stars

Black French Sole Onstage

Black French Sole Onstage

+1

Brand Name: French Sole
Product Name: Onstage
Color: Black Patent/Black Suede
Price: $195.00
Rating: 5Rated 5 stars out of 5(26)

Eastland 1955 Edition - Newbury. Color Black Leather. On sale for $74.95. MSRP $100.00.. 4.2 out of 5 stars

Black Eastland 1955 Edition Newbury

Black Eastland 1955 Edition Newbury

+2 colors/patterns

Brand Name: Eastland 1955 Edition
Product Name: Newbury
Color: Black Leather
Price: $74.95MSRP: $100.00
Rating: 4Rated 4 stars out of 5(15)

Merrell - Jungle Moc. Color Midnight Pig Suede. $99.95. 4.5 out of 5 stars

Black Merrell Jungle Moc

+2

Brand Name: Merrell
Product Name: Jungle Moc
Color: Midnight Pig Suede
Price: $99.95
Rating: 5Rated 5 stars out of 5(2283)

Get on the List

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