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

Size 8.5 Gray Ankle Boots and Booties

66 items found

Sort By

Your Selections

Search Results

Nine West - Texen. Color Light Grey. $138.99. 4.0 out of 5 stars

Gray Nine West Texen

Gray Nine West Texen

+4

Brand Name: Nine West
Product Name: Texen
Color: Light Grey
Price: $138.99
Rating: 4Rated 4 stars out of 5(4)

Born - Tarkiln. Color Grey Distressed. $135.00. 4.1 out of 5 stars

Gray Born Tarkiln

Gray Born Tarkiln

+4

Brand Name: Born
Product Name: Tarkiln
Color: Grey Distressed
Price: $135.00
Rating: 4Rated 4 stars out of 5(805)

Kork-Ease - Chandra II. Color Grey. $210.00. 4.0 out of 5 stars

Gray Kork-Ease Chandra II

Gray Kork-Ease Chandra II

+2

Brand Name: Kork-Ease
Product Name: Chandra II
Color: Grey
Price: $210.00
Rating: 4Rated 4 stars out of 5(1)

SoftWalk - Helena. Color Stone Suede. $124.95. 4.2 out of 5 stars

Gray SoftWalk Helena

Gray SoftWalk Helena

+3

Brand Name: SoftWalk
Product Name: Helena
Color: Stone Suede
Price: $124.95
Rating: 4Rated 4 stars out of 5(179)

Lucky Brand - Kenadie. Color Charcoal. On sale for $95.61. MSRP $159.00.. 3.7 out of 5 stars

+3

Brand Name: Lucky Brand
Product Name: Kenadie
Color: Charcoal
Price: $95.61MSRP: $159.00
Rating: 4Rated 4 stars out of 5(3)

Lucky Brand - Callam. Color Charcoal. On sale for $95.33. MSRP $149.00.. 3.7 out of 5 stars

Brand Name: Lucky Brand
Product Name: Callam
Color: Charcoal
Price: $95.33MSRP: $149.00
Rating: 4Rated 4 stars out of 5(3)

David Tate - Blade. Color Gray Pebble Grain Leather. On sale for $78.18. MSRP $169.95.. 4.6 out of 5 stars

Gray David Tate Blade

Gray David Tate Blade

+2

Brand Name: David Tate
Product Name: Blade
Color: Gray Pebble Grain Leather
Price: $78.18MSRP: $169.95
Rating: 5Rated 5 stars out of 5(5)

Alegria - Symone. Color Coal. On sale for $134.59. MSRP $147.90.. 2.0 out of 5 stars

Gray Alegria Symone

Gray Alegria Symone

Brand Name: Alegria
Product Name: Symone
Color: Coal
Price: $134.59MSRP: $147.90
Rating: 2Rated 2 stars out of 5(1)

Spring Step - Smokies. Color Light Grey. $119.95. 5.0 out of 5 stars

Gray Spring Step Smokies

Gray Spring Step Smokies

+5

Brand Name: Spring Step
Product Name: Smokies
Color: Light Grey
Price: $119.95
Rating: 5Rated 5 stars out of 5(1)

Miz Mooz - Joelene. Color Graphite. On sale for $111.27. MSRP $209.95.. 1.0 out of 5 stars

Gray Miz Mooz Joelene

Gray Miz Mooz Joelene

+2

Brand Name: Miz Mooz
Product Name: Joelene
Color: Graphite
Price: $111.27MSRP: $209.95
Rating: 1Rated 1 star out of 5(1)

David Tate - Bellview. Color Gray Antique Suede. $169.95. 5.0 out of 5 stars

Gray David Tate Bellview

Gray David Tate Bellview

+2

Brand Name: David Tate
Product Name: Bellview
Color: Gray Antique Suede
Price: $169.95
Rating: 5Rated 5 stars out of 5(10)

TOMS - Constance. Color Sahara Mini Cheetah Suede. On sale for $56.38. MSRP $119.95.. 3.8 out of 5 stars

Gray TOMS Constance

Gray TOMS Constance

+5

Brand Name: TOMS
Product Name: Constance
Color: Sahara Mini Cheetah Suede
Price: $56.38MSRP: $119.95
Rating: 4Rated 4 stars out of 5(9)

Dolce Vita - Hilde. Color Ivory Leather. On sale for $152.95. MSRP $170.00.. 3.0 out of 5 stars

Gray Dolce Vita Hilde

Gray Dolce Vita Hilde

+2

Brand Name: Dolce Vita
Product Name: Hilde
Color: Ivory Leather
Price: $152.95MSRP: $170.00
Rating: 3Rated 3 stars out of 5(4)

Lucky Brand - Basel. Color Griffin. On sale for $80.59. MSRP $139.00.. 4.1 out of 5 stars

+4

Brand Name: Lucky Brand
Product Name: Basel
Color: Griffin
Price: $80.59MSRP: $139.00
Rating: 4Rated 4 stars out of 5(141)

David Tate - Cutey. Color Gray Suede. On sale for $110.27. MSRP $154.95.. 4.6 out of 5 stars

Gray David Tate Cutey

Gray David Tate Cutey

+3

Brand Name: David Tate
Product Name: Cutey
Color: Gray Suede
Price: $110.27MSRP: $154.95
Rating: 5Rated 5 stars out of 5(10)

Blondo - Prestly Waterproof. Color Fallen Rock Suede. On sale for $127.07. MSRP $149.95.. 3.6 out of 5 stars

Gray Blondo Prestly Waterproof

Gray Blondo Prestly Waterproof

+4

Brand Name: Blondo
Product Name: Prestly Waterproof
Color: Fallen Rock Suede
Price: $127.07MSRP: $149.95
Rating: 4Rated 4 stars out of 5(13)

TOMS - Clare. Color Sahara Mini Cheetah Suede. On sale for $64.97. MSRP $99.95.. 3.3 out of 5 stars

Gray TOMS Clare

Gray TOMS Clare

+4

Brand Name: TOMS
Product Name: Clare
Color: Sahara Mini Cheetah Suede
Price: $64.97MSRP: $99.95
Rating: 3Rated 3 stars out of 5(6)

DV Dolce Vita - Keilani. Color Mushroom. On sale for $51.20. MSRP $80.00.. 2.0 out of 5 stars

Gray DV Dolce Vita Keilani

Gray DV Dolce Vita Keilani

+2

Brand Name: DV Dolce Vita
Product Name: Keilani
Color: Mushroom
Price: $51.20MSRP: $80.00
Rating: 2Rated 2 stars out of 5(2)

Blondo - Alida Waterproof. Color Fallen Rock Suede. $149.94. 4.4 out of 5 stars

Gray Blondo Alida Waterproof

Gray Blondo Alida Waterproof

+4

Brand Name: Blondo
Product Name: Alida Waterproof
Color: Fallen Rock Suede
Price: $149.94
Rating: 4Rated 4 stars out of 5(43)

Blondo - Valen Waterproof. Color Fallen Rock Suede. On sale for $113.87. MSRP $169.95.. 3.8 out of 5 stars

Gray Blondo Valen Waterproof

Gray Blondo Valen Waterproof

+2

Brand Name: Blondo
Product Name: Valen Waterproof
Color: Fallen Rock Suede
Price: $113.87MSRP: $169.95
Rating: 4Rated 4 stars out of 5(4)

Stuart Weitzman - Stuart 75 Zip Bootie. Color New Pyrite. On sale for $455.00. MSRP $650.00.. 3.0 out of 5 stars

Gray Stuart Weitzman Stuart 75 Zip Bootie

Gray Stuart Weitzman Stuart 75 Zip Bootie

+3

Brand Name: Stuart Weitzman
Product Name: Stuart 75 Zip Bootie
Color: New Pyrite
Price: $455.00MSRP: $650.00
Rating: 3Rated 3 stars out of 5(3)

Vince - Charli. Color Macadamia. On sale for $250.99. MSRP $395.00..

Gray Vince Charli

Gray Vince Charli

+2

Brand Name: Vince
Product Name: Charli
Color: Macadamia
Price: $250.99MSRP: $395.00
Rating

Comfortiva - Holland. Color Light Grey. $129.95. 3.2 out of 5 stars

Gray Comfortiva Holland

Gray Comfortiva Holland

+3

Brand Name: Comfortiva
Product Name: Holland
Color: Light Grey
Price: $129.95
Rating: 3Rated 3 stars out of 5(4)

Blondo - Sinner Waterproof. Color Fallen Rock Suede. On sale for $95.80. MSRP $159.95.. 5.0 out of 5 stars

Gray Blondo Sinner Waterproof

Gray Blondo Sinner Waterproof

+4

Brand Name: Blondo
Product Name: Sinner Waterproof
Color: Fallen Rock Suede
Price: $95.80MSRP: $159.95
Rating: 5Rated 5 stars out of 5(1)

Dansko - Mitzy. Color Stone Burnished Suede. Low Stock. On sale for $123.47. MSRP $189.95.. 4.0 out of 5 stars

10 left in stock

Gray Dansko Mitzy

Gray Dansko Mitzy

+2

Brand Name: Dansko
Product Name: Mitzy
Color: Stone Burnished Suede
Price: $123.47MSRP: $189.95
Rating: 4Rated 4 stars out of 5(5)

Comfortiva - Carter. Color Moon Grey/Denim. On sale for $92.97. MSRP $149.95.. 3.2 out of 5 stars

Gray Comfortiva Carter

Gray Comfortiva Carter

+2

Brand Name: Comfortiva
Product Name: Carter
Color: Moon Grey/Denim
Price: $92.97MSRP: $149.95
Rating: 3Rated 3 stars out of 5(4)

Clarks - Charlten Ave. Color Slate Nubuck. On sale for $89.68. MSRP $130.00.. 3.0 out of 5 stars

Gray Clarks Charlten Ave

Gray Clarks Charlten Ave

+2

Brand Name: Clarks
Product Name: Charlten Ave
Color: Slate Nubuck
Price: $89.68MSRP: $130.00
Rating: 3Rated 3 stars out of 5(6)

Aetrex - Kara. Color Charcoal. On sale for $122.33. MSRP $179.95.. 4.0 out of 5 stars

Gray Aetrex Kara

Gray Aetrex Kara

Brand Name: Aetrex
Product Name: Kara
Color: Charcoal
Price: $122.33MSRP: $179.95
Rating: 4Rated 4 stars out of 5(2)

SoftWalk - Roselle. Color Dark Grey. $149.94. 3.8 out of 5 stars

Gray SoftWalk Roselle

Gray SoftWalk Roselle

+2

Brand Name: SoftWalk
Product Name: Roselle
Color: Dark Grey
Price: $149.94
Rating: 4Rated 4 stars out of 5(24)

Spring Step - Wildwest. Color Grey. $169.95. 2.0 out of 5 stars

Gray Spring Step Wildwest

Gray Spring Step Wildwest

+4

Brand Name: Spring Step
Product Name: Wildwest
Color: Grey
Price: $169.95
Rating: 2Rated 2 stars out of 5(1)

L'Artiste by Spring Step - Adelvice-Fleur. Color Grey Multi. Low Stock. $149.95. 5.0 out of 5 stars

9 left in stock

Gray L'Artiste by Spring Step Adelvice-Fleur

Gray L'Artiste by Spring Step Adelvice-Fleur

+2

Brand Name: L'Artiste by Spring Step
Product Name: Adelvice-Fleur
Color: Grey Multi
Price: $149.95
Rating: 5Rated 5 stars out of 5(1)

Lucky Brand - Mikasi. Color Excalibur. On sale for $88.93. MSRP $139.00.. 4.7 out of 5 stars

Brand Name: Lucky Brand
Product Name: Mikasi
Color: Excalibur
Price: $88.93MSRP: $139.00
Rating: 5Rated 5 stars out of 5(6)

LifeStride - Blake Zip. Color Ash. On sale for $54.99. MSRP $89.99.. 3.3 out of 5 stars

Gray LifeStride Blake Zip

Gray LifeStride Blake Zip

+3

Brand Name: LifeStride
Product Name: Blake Zip
Color: Ash
Price: $54.99MSRP: $89.99
Rating: 3Rated 3 stars out of 5(7)

VIONIC - Hazal. Color Stone Suede. $179.95. 4.5 out of 5 stars

Gray VIONIC Hazal

Gray VIONIC Hazal

+3

Brand Name: VIONIC
Product Name: Hazal
Color: Stone Suede
Price: $179.95
Rating: 4Rated 4 stars out of 5(160)

Stuart Weitzman - 5050 Bold Zip Bootie. Color Charcoal. On sale for $386.75. MSRP $595.00.. 4.9 out of 5 stars

Gray Stuart Weitzman 5050 Bold Zip Bootie

Gray Stuart Weitzman 5050 Bold Zip Bootie

+3

Brand Name: Stuart Weitzman
Product Name: 5050 Bold Zip Bootie
Color: Charcoal
Price: $386.75MSRP: $595.00
Rating: 5Rated 5 stars out of 5(11)

LifeStride - Alexander. Color Grey. On sale for $59.77. MSRP $79.99.. 4.0 out of 5 stars

Gray LifeStride Alexander

Gray LifeStride Alexander

+3

Brand Name: LifeStride
Product Name: Alexander
Color: Grey
Price: $59.77MSRP: $79.99
Rating: 4Rated 4 stars out of 5(8)

Dr. Scholl's - Chloe. Color Grey Fabric. On sale for $73.61. MSRP $120.00.. 3.8 out of 5 stars

Gray Dr. Scholl's Chloe

Gray Dr. Scholl's Chloe

Brand Name: Dr. Scholl's
Product Name: Chloe
Color: Grey Fabric
Price: $73.61MSRP: $120.00
Rating: 4Rated 4 stars out of 5(15)

SOREL - Evie™ Ii Zip. Color Quarry/Grill. On sale for $83.97. MSRP $150.00.. 4.1 out of 5 stars

Gray SOREL Evie™ Ii Zip

Gray SOREL Evie™ Ii Zip

+4

Brand Name: SOREL
Product Name: Evie™ Ii Zip
Color: Quarry/Grill
Price: $83.97MSRP: $150.00
Rating: 4Rated 4 stars out of 5(81)

Johnston & Murphy - Trista Perfed Double Zip Bootie. Color Dark Gray Suede. Low Stock. On sale for $79.18. MSRP $198.00.. 4.5 out of 5 stars

2 left in stock

Gray Johnston & Murphy Trista Perfed Double Zip Bootie

Gray Johnston & Murphy Trista Perfed Double Zip Bootie

+2

Brand Name: Johnston & Murphy
Product Name: Trista Perfed Double Zip Bootie
Color: Dark Gray Suede
Price: $79.18MSRP: $198.00
Rating: 5Rated 5 stars out of 5(2)

Blowfish Malibu - Stacie. Color Sea Mushroom Prospector/Down Under/Dyecut. Low Stock. On sale for $55.58. MSRP $69.99.. 4.7 out of 5 stars

6 left in stock

Gray Blowfish Malibu Stacie

Gray Blowfish Malibu Stacie

+1

Brand Name: Blowfish Malibu
Product Name: Stacie
Color: Sea Mushroom Prospector/Down Under/Dyecut
Price: $55.58MSRP: $69.99
Rating: 5Rated 5 stars out of 5(6)

Bzees - Gloria. Color Dark Grey Fabric. $110.00. 4.6 out of 5 stars

Gray Bzees Gloria

Gray Bzees Gloria

+2

Brand Name: Bzees
Product Name: Gloria
Color: Dark Grey Fabric
Price: $110.00
Rating: 5Rated 5 stars out of 5(41)

Bzees - Glacier. Color Grey Fabric. On sale for $76.57. MSRP $95.00.. 4.2 out of 5 stars

Gray Bzees Glacier

Gray Bzees Glacier

+2

Brand Name: Bzees
Product Name: Glacier
Color: Grey Fabric
Price: $76.57MSRP: $95.00
Rating: 4Rated 4 stars out of 5(5)

Sofft - Emeree. Color Steel Grey. $139.95. 4.1 out of 5 stars

Gray Sofft Emeree

Gray Sofft Emeree

+5

Brand Name: Sofft
Product Name: Emeree
Color: Steel Grey
Price: $139.95
Rating: 4Rated 4 stars out of 5(26)

Bandolino - Gilbert 3. Color Dove 23. Low Stock. On sale for $76.08. MSRP $129.00.. 4.0 out of 5 stars

5 left in stock

Gray Bandolino Gilbert 3

Gray Bandolino Gilbert 3

+2

Brand Name: Bandolino
Product Name: Gilbert 3
Color: Dove 23
Price: $76.08MSRP: $129.00
Rating: 4Rated 4 stars out of 5(3)

Mephisto - Rezia. Color Fog Distressed Nubuck. $318.95. 4.6 out of 5 stars

Gray Mephisto Rezia

Gray Mephisto Rezia

+3

Brand Name: Mephisto
Product Name: Rezia
Color: Fog Distressed Nubuck
Price: $318.95
Rating: 5Rated 5 stars out of 5(12)

Eric Michael - Dana. Color Grey. Low Stock. $189.00. 3.7 out of 5 stars

10 left in stock

Gray Eric Michael Dana

Gray Eric Michael Dana

+3

Brand Name: Eric Michael
Product Name: Dana
Color: Grey
Price: $189.00
Rating: 4Rated 4 stars out of 5(6)

Josef Seibel - Caren 09. Color Gray. Low Stock. On sale for $130.50. MSRP $150.00.. 4.2 out of 5 stars

6 left in stock

Gray Josef Seibel Caren 09

Gray Josef Seibel Caren 09

+2

Brand Name: Josef Seibel
Product Name: Caren 09
Color: Gray
Price: $130.50MSRP: $150.00
Rating: 4Rated 4 stars out of 5(19)

Blondo - Noelle Waterproof. Color Grey Suede. On sale for $133.67. MSRP $149.00.. 3.0 out of 5 stars

Gray Blondo Noelle Waterproof

Gray Blondo Noelle Waterproof

+5

Brand Name: Blondo
Product Name: Noelle Waterproof
Color: Grey Suede
Price: $133.67MSRP: $149.00
Rating: 3Rated 3 stars out of 5(9)

Easy Street - Fernanda. Color Grey. Low Stock. $59.99. 2.7 out of 5 stars

2 left in stock

Gray Easy Street Fernanda

Gray Easy Street Fernanda

+3

Brand Name: Easy Street
Product Name: Fernanda
Color: Grey
Price: $59.99
Rating: 3Rated 3 stars out of 5(3)

Eric Michael - Olivia. Color Grey. Low Stock. On sale for $156.75. MSRP $209.00.. 3.0 out of 5 stars

5 left in stock

Gray Eric Michael Olivia

Gray Eric Michael Olivia

+3

Brand Name: Eric Michael
Product Name: Olivia
Color: Grey
Price: $156.75MSRP: $209.00
Rating: 3Rated 3 stars out of 5(1)

Bueno - Tilly. Color Grey. Low Stock. $140.00. 3.3 out of 5 stars

3 left in stock

Gray Bueno Tilly

Gray Bueno Tilly

+2

Brand Name: Bueno
Product Name: Tilly
Color: Grey
Price: $140.00
Rating: 3Rated 3 stars out of 5(3)

David Tate - Skip. Color Grey. On sale for $124.21. MSRP $159.95.. 3.7 out of 5 stars

Gray David Tate Skip

Gray David Tate Skip

+2

Brand Name: David Tate
Product Name: Skip
Color: Grey
Price: $124.21MSRP: $159.95
Rating: 4Rated 4 stars out of 5(13)

Propet - Waverly. Color Grey Suede. $119.95. 4.0 out of 5 stars

Gray Propet Waverly

Gray Propet Waverly

+4

Brand Name: Propet
Product Name: Waverly
Color: Grey Suede
Price: $119.95
Rating: 4Rated 4 stars out of 5(186)

LifeStride - Jersey. Color Iron Grey. On sale for $61.53. MSRP $109.99.. 4.3 out of 5 stars

Gray LifeStride Jersey

Gray LifeStride Jersey

Brand Name: LifeStride
Product Name: Jersey
Color: Iron Grey
Price: $61.53MSRP: $109.99
Rating: 4Rated 4 stars out of 5(29)

Roper - Ava. Color Brown 4. On sale for $59.80. MSRP $70.00.. 4.1 out of 5 stars

Gray Roper Ava

Gray Roper Ava

+10

Brand Name: Roper
Product Name: Ava
Color: Brown 4
Price: $59.80MSRP: $70.00
Rating: 4Rated 4 stars out of 5(33)

TOMS - Kallie. Color Pavement Grey Suede. On sale for $69.54. MSRP $99.95.. 3.6 out of 5 stars

Gray TOMS Kallie

Gray TOMS Kallie

+4

Brand Name: TOMS
Product Name: Kallie
Color: Pavement Grey Suede
Price: $69.54MSRP: $99.95
Rating: 4Rated 4 stars out of 5(125)

Anodyne - No. 91 Casual Boot. Color Grey. On sale for $155.00. MSRP $159.00.. 3.0 out of 5 stars

Gray Anodyne No. 91 Casual Boot

Gray Anodyne No. 91 Casual Boot

+2

Brand Name: Anodyne
Product Name: No. 91 Casual Boot
Color: Grey
Price: $155.00MSRP: $159.00
Rating: 3Rated 3 stars out of 5(29)

Arcopedico - Luana. Color Grey Suede. $134.95. 4.0 out of 5 stars

Gray Arcopedico Luana

Gray Arcopedico Luana

+3

Brand Name: Arcopedico
Product Name: Luana
Color: Grey Suede
Price: $134.95
Rating: 4Rated 4 stars out of 5(65)

Born - Kerri. Color Dark Grey Distressed. $130.00. 4.4 out of 5 stars

Gray Born Kerri

Gray Born Kerri

+7

Brand Name: Born
Product Name: Kerri
Color: Dark Grey Distressed
Price: $130.00
Rating: 4Rated 4 stars out of 5(649)

LifeStride - Prairie. Color Ash. On sale for $57.51. MSRP $89.99.. 4.1 out of 5 stars

Gray LifeStride Prairie

Gray LifeStride Prairie

+3

Brand Name: LifeStride
Product Name: Prairie
Color: Ash
Price: $57.51MSRP: $89.99
Rating: 4Rated 4 stars out of 5(121)

Arcopedico - L19. Color Grey Suede. $144.95. 4.4 out of 5 stars

Gray Arcopedico L19

Gray Arcopedico L19

+10

Brand Name: Arcopedico
Product Name: L19
Color: Grey Suede
Price: $144.95
Rating: 4Rated 4 stars out of 5(597)

Propet - Delaney Alpine. Color Grey. Low Stock. On sale for $53.02. MSRP $84.95.. 4.1 out of 5 stars

2 left in stock

Gray Propet Delaney Alpine

Gray Propet Delaney Alpine

Brand Name: Propet
Product Name: Delaney Alpine
Color: Grey
Price: $53.02MSRP: $84.95
Rating: 4Rated 4 stars out of 5(29)

Dr. Scholl's - Create. Color Mid Grey. On sale for $70.37. MSRP $100.00.. 3.8 out of 5 stars

Gray Dr. Scholl's Create

Gray Dr. Scholl's Create

+2

Brand Name: Dr. Scholl's
Product Name: Create
Color: Mid Grey
Price: $70.37MSRP: $100.00
Rating: 4Rated 4 stars out of 5(109)

Dr. Scholl's - Rate. Color Dark Shadow Grey Microfiber Perf. On sale for $65.09. MSRP $90.00.. 4.4 out of 5 stars

Gray Dr. Scholl's Rate

Gray Dr. Scholl's Rate

+3

Brand Name: Dr. Scholl's
Product Name: Rate
Color: Dark Shadow Grey Microfiber Perf
Price: $65.09MSRP: $90.00
Rating: 4Rated 4 stars out of 5(374)

Eric Michael - London. Color Grey. Low Stock. $194.95. 4.2 out of 5 stars

8 left in stock

Gray Eric Michael London

Gray Eric Michael London

+2

Brand Name: Eric Michael
Product Name: London
Color: Grey
Price: $194.95
Rating: 4Rated 4 stars out of 5(238)

LifeStride - Adriana. Color Mushroom. On sale for $58.97. MSRP $89.99.. 4.2 out of 5 stars

Gray LifeStride Adriana

Gray LifeStride Adriana

+3

Brand Name: LifeStride
Product Name: Adriana
Color: Mushroom
Price: $58.97MSRP: $89.99
Rating: 4Rated 4 stars out of 5(187)

Get on the List

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