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

Size 8.5 Casual Winter Shoes

51 items found

Sort By

Your Selections

Search Results

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
Gender: Women's
Color: Midnight Pig Suede
Price: $99.95
Rating: 5Rated 5 stars out of 5(2266)

SOREL - Out N About™ III Classic. Color Black/Sea Salt. On sale for $68.87. MSRP $130.00.. 4.2 out of 5 stars

Black SOREL Out N About™ III Classic

Black SOREL Out N About™ III Classic

+8

Brand Name: SOREL
Product Name: Out N About™ III Classic
Gender: Women's
Color: Black/Sea Salt
Price: $68.87MSRP: $130.00
Rating: 4Rated 4 stars out of 5(1187)

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
Gender: Women's
Color: New Tan
Price: $105.00
Rating: 5Rated 5 stars out of 5(1118)

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
Gender: Women's
Color: Camel
Price: $79.95MSRP: $100.00
Rating: 4Rated 4 stars out of 5(100)

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
Gender: Women's
Color: Black Synthetic
Price: $49.99MSRP: $79.99
Rating: 4Rated 4 stars out of 5(79)

LifeStride - Margot. Color Black. 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
Gender: Women's
Color: Black
Price: $49.99MSRP: $69.99
Rating: 4Rated 4 stars out of 5(148)

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

Blue Dansko Kane

Blue Dansko Kane

+3

Brand Name: Dansko
Product Name: Kane
Gender: Women's
Color: Blue Molded
Price: $84.95
Rating: 4Rated 4 stars out of 5(296)

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

Pink Naturalizer Maxwell

Pink Naturalizer Maxwell

+15

Brand Name: Naturalizer
Product Name: Maxwell
Gender: Women's
Color: Vintage Mauve
Price: $79.95MSRP: $89.00
Rating: 4Rated 4 stars out of 5(422)

Dansko - Professional. Color Antique Tooled. On sale for $119.99. MSRP $145.00.. 4.4 out of 5 stars

Gold Dansko Professional

Gold Dansko Professional

Brand Name: Dansko
Product Name: Professional
Gender: Women's
Color: Antique Tooled
Price: $119.99MSRP: $145.00
Rating: 4Rated 4 stars out of 5(1561)

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
Gender: Women's
Color: Black Patent/Black Suede
Price: $195.00
Rating: 5Rated 5 stars out of 5(26)

SoftWalk - Willis. Color Dark Grey Patent. Low Stock. On sale for $69.98. MSRP $119.95.. 3.7 out of 5 stars

4 left in stock

Gray SoftWalk Willis

Gray SoftWalk Willis

+3

Brand Name: SoftWalk
Product Name: Willis
Gender: Women's
Color: Dark Grey Patent
Price: $69.98MSRP: $119.95
Rating: 4Rated 4 stars out of 5(277)

LifeStride - Zee. Color Black. On sale for $49.99. MSRP $79.99.. 4.2 out of 5 stars

Black LifeStride Zee

Black LifeStride Zee

+3

Brand Name: LifeStride
Product Name: Zee
Gender: Women's
Color: Black
Price: $49.99MSRP: $79.99
Rating: 4Rated 4 stars out of 5(181)

Alegria - Keli Professional. Color Black Nappa Leather. $129.00. 4.1 out of 5 stars

Black Alegria Keli Professional

Black Alegria Keli Professional

Brand Name: Alegria
Product Name: Keli Professional
Gender: Women's
Color: Black Nappa Leather
Price: $129.00
Rating: 4Rated 4 stars out of 5(565)

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
Gender: Women's
Color: Andorra/Orange
Price: $71.21MSRP: $95.00
Rating: 4Rated 4 stars out of 5(203)

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

Black Aetrex Libby

Black Aetrex Libby

+2

Brand Name: Aetrex
Product Name: Libby
Gender: Women's
Color: Black
Price: $139.90
Rating: 4Rated 4 stars out of 5(63)

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
Gender: Women's
Color: Navy Leather
Price: $109.95
Rating: 4Rated 4 stars out of 5(65)

Eastland 1955 Edition - Newbury. Color Black Leather. On sale for $85.00. 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
Gender: Women's
Color: Black Leather
Price: $85.00MSRP: $100.00
Rating: 4Rated 4 stars out of 5(15)

Ariat - Cruiser. Color Brown Bomber/Ariat Logo. On sale for $65.97. MSRP $89.95.. 4.6 out of 5 stars

Brown Ariat Cruiser

Brown Ariat Cruiser

+23

Brand Name: Ariat
Product Name: Cruiser
Gender: Women's
Color: Brown Bomber/Ariat Logo
Price: $65.97MSRP: $89.95
Rating: 5Rated 5 stars out of 5(1092)

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
Gender: Women's
Color: Dark Charcoal Ragg Wool
Price: $46.95
Rating: 4Rated 4 stars out of 5(176)

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
Gender: Women's
Color: Black/White
Price: $84.95MSRP: $100.00
Rating: 4Rated 4 stars out of 5(29)

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
Gender: Women's
Color: Ewe Woven Tweed
Price: $47.95
Rating: 4Rated 4 stars out of 5(800)

Alegria - Debra. Color Depth Perception. On sale for $102.70. MSRP $130.00.. 3.8 out of 5 stars

Black Alegria Debra

Black Alegria Debra

Brand Name: Alegria
Product Name: Debra
Gender: Women's
Color: Depth Perception
Price: $102.70MSRP: $130.00
Rating: 4Rated 4 stars out of 5(47)

Orthofeet - Florence. Color Brown. On sale for $99.20. MSRP $160.00.. 4.7 out of 5 stars

Brown Orthofeet Florence

Brown Orthofeet Florence

Brand Name: Orthofeet
Product Name: Florence
Gender: Women's
Color: Brown
Price: $99.20MSRP: $160.00
Rating: 5Rated 5 stars out of 5(3)

Sperry - Saltwater Alpine. Color White. On sale for $61.37. 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
Gender: Women's
Color: White
Price: $61.37MSRP: $110.00
Rating: 4Rated 4 stars out of 5(113)

Propet - Demi. Color White. On sale for $96.70. MSRP $109.95.. 4.0 out of 5 stars

White Propet Demi

White Propet Demi

+4

Brand Name: Propet
Product Name: Demi
Gender: Women's
Color: White
Price: $96.70MSRP: $109.95
Rating: 4Rated 4 stars out of 5(4)

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
Gender: Women's
Color: Black
Price: $74.95
Rating: 3Rated 3 stars out of 5(77)

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
Gender: Unisex
Color: Charcoal
Price: $104.95
Rating: 5Rated 5 stars out of 5(320)

Lucky Brand - Hybiscus. Color Silver Cloud. On sale for $131.37. MSRP $219.00.. 4.2 out of 5 stars

+3

Brand Name: Lucky Brand
Product Name: Hybiscus
Gender: Women's
Color: Silver Cloud
Price: $131.37MSRP: $219.00
Rating: 4Rated 4 stars out of 5(25)

Acorn - Lightweight Bristol Loafer. Color Navy/Blue. Low Stock. $46.95. 4.0 out of 5 stars

10 left in stock

Multi Acorn Lightweight Bristol Loafer

Multi Acorn Lightweight Bristol Loafer

+2

Brand Name: Acorn
Product Name: Lightweight Bristol Loafer
Gender: Women's
Color: Navy/Blue
Price: $46.95
Rating: 4Rated 4 stars out of 5(142)

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

Multi Chaco Ramble Puff Clog

Multi Chaco Ramble Puff Clog

+2

Brand Name: Chaco
Product Name: Ramble Puff Clog
Gender: Women's
Color: Ash Gray
Price: $74.95
Rating: 4Rated 4 stars out of 5(10)

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
Gender: Women's
Color: Light Brown Oil Nubuck
Price: $184.99
Rating

Dirty Laundry - Nirvana. Color White Chill Smooth. On sale for $57.99. 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
Gender: Women's
Color: White Chill Smooth
Price: $57.99MSRP: $64.95
Rating: 3Rated 3 stars out of 5(3)

La Canadienne - Douglas. Color Black Crinkle Patent. On sale for $318.75. MSRP $425.00.. 4.3 out of 5 stars

Black La Canadienne Douglas

Black La Canadienne Douglas

Brand Name: La Canadienne
Product Name: Douglas
Gender: Women's
Color: Black Crinkle Patent
Price: $318.75MSRP: $425.00
Rating: 4Rated 4 stars out of 5(6)

Frye - Veronica Harness Short. Color Caramel. Low Stock. On sale for $175.79. 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
Gender: Women's
Color: Caramel
Price: $175.79MSRP: $298.00
Rating: 4Rated 4 stars out of 5(16)

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

10 left in stock

Black Klogs Footwear Moxy

Black Klogs Footwear Moxy

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

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
Gender: Women's
Color: Black
Price: $98.95
Rating: 5Rated 5 stars out of 5(1)

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
Gender: Women's
Color: Almond Blossom
Price: $71.00
Rating: 4Rated 4 stars out of 5(13)

Vans - Standard™ Snow MTE™. Color Grey. On sale for $100.77. 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™
Gender: Unisex
Color: Grey
Price: $100.77MSRP: $180.00
Rating: 4Rated 4 stars out of 5(9)

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
Gender: Women's
Color: Black
Price: $99.99
Rating: 4Rated 4 stars out of 5(8)

The North Face - Storm Strike III Waterproof. Color Deep Taupe/TNF Black. Low Stock. On sale for $88.93. MSRP $139.00.. 2.7 out of 5 stars

8 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
Gender: Women's
Color: Deep Taupe/TNF Black
Price: $88.93MSRP: $139.00
Rating: 3Rated 3 stars out of 5(3)

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
Gender: Women's
Color: Bison Brown Oil Tan
Price: $179.99
Rating

Carhartt - WP 8" Ins. Wedge Fold Down Winter Boot. Color Dark Grey Nubuck. $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
Gender: Women's
Color: Dark Grey Nubuck
Price: $179.99
Rating

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
Gender: Unisex
Color: Light Blue
Price: $136.76MSRP: $190.00
Rating: 5Rated 5 stars out of 5(1)

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
Gender: Women's
Color: Black Leather
Price: $585.00
Rating: 5Rated 5 stars out of 5(24)

SOREL - Explorer™ II Carnival Cozy. Color Black/Sea Salt. On sale for $104.96. MSRP $140.00.. 4.2 out of 5 stars

Black SOREL Explorer™ II Carnival Cozy

Black SOREL Explorer™ II Carnival Cozy

+3

Brand Name: SOREL
Product Name: Explorer™ II Carnival Cozy
Gender: Women's
Color: Black/Sea Salt
Price: $104.96MSRP: $140.00
Rating: 4Rated 4 stars out of 5(229)

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
Gender: Women's
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
Gender: Women's
Color: New Wheat
Price: $137.70MSRP: $170.00
Rating: 5Rated 5 stars out of 5(4)

Kamik - Rogue Hike 3. Color Black. Low Stock. $119.99. 4.3 out of 5 stars

4 left in stock

Black Kamik Rogue Hike 3

Black Kamik Rogue Hike 3

+3

Brand Name: Kamik
Product Name: Rogue Hike 3
Gender: Women's
Color: Black
Price: $119.99
Rating: 4Rated 4 stars out of 5(3)

Steve Madden - Pop Winter Boot. Color Black. On sale for $84.03. 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
Gender: Women's
Color: Black
Price: $84.03MSRP: $99.95
Rating: 3Rated 3 stars out of 5(5)

JBU - Free Bird. Color Gunmetal. On sale for $61.03. 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
Gender: Women's
Color: Gunmetal
Price: $61.03MSRP: $74.50
Rating: 3Rated 3 stars out of 5(5)

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
Gender: Women's
Color: Black
Price: $112.34MSRP: $139.00
Rating

Get on the List

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