Explore Men's Grey Ankle Boots. From Trendy To Timeless

Dolce & Gabbana

Leather Ankle Boots

From: Italist

$726.54

Diemme

Roccia Ankle Boots

From: Eraldo

Sizes:

8, 9, 10, 11, 12

$528.00

Hogan

Elastic Side Panel Chelsea Ankle Boots

From: SHOP SIMON

Sizes:

7, 8, 9, 10

$914.81

Common Projects

Chelsea Ankle Boots

From: Biffi Boutique

Sizes:

9, 11

$353.81

$505.44

-30%

All Saints

Ankle Boots

From: AllSaints

$179.00

$299.00

-40%

Camper

Ankle Boots In Laminated Leather

From: GIGLIO

$107.45

Columbia

Fairbank Snow Boots

From: SHOP SIMON

$59.99

$70.00

-14%

Camper

Ankle Boots In Laminated Leather

From: GIGLIO

$122.76

ECCO

Metropole Prague - Leather Chukka Boots

From: ECCO

Sizes:

6, 7, 8, 9, 10, 11, 12, 13

$240.00

Tod's

Chelsea Suede Leather Ankle Boots

From: Lungolivigno Fashion

Sizes:

7, 8, 9, 10, 11

$605.00

$757.00

-20%

Vance Co.

Jimmy Plain Toe Chukka Boots

From: SHOP SIMON

$55.00

$109.99

-50%

Camper

Ankle Boots

From: SHOP SIMON

$235.00

Dolce & Gabbana

Stretch Mesh Ankle Boots

From: Italist

$320.46

Bottega Veneta

Dawson Intrecciato Leather Chukka Boots

From: Bergdorf Goodman

Sizes:

8, 10, 11

$1,600.00

Dr. Martens

Combs Jungle Ankle Boots

From: SHOP SIMON

Sizes:

8

$140.00

$175.00

-20%

Dolce & Gabbana

Ankle Strap Boots

From: Italist

$454.75

Doucal's

Chukka Boots Color Grey

From: GIGLIO

Sizes:

8.5

$306.59

$437.99

-30%

John Varvatos

Morrison Sharpei Ankle Boots

From: Neiman Marcus

$798.00

Doucal's

Suede Ankle Boots

From: SHOP SIMON

$430.57

$468.70

-8%

Columbia

Fairbanks Waterproof Ankle Snow Boots

From: SHOP SIMON

$75.00

$90.00

-17%

Santoni

Detroit Slip-on Suede Chukka Boots

From: Neiman Marcus

Sizes:

7, 7.5, 9, 9.5, 11, 12, 13

$890.00

Camper

Ankle Boots

From: SHOP SIMON

$245.00

Dolce & Gabbana

Light Gray Chelsea Short Ankle Boots

From: Italist

$576.26

Vance Co.

Lucien Cap Toe Ankle Boots

From: SHOP SIMON

Sizes:

8, 9, 13

$59.99

$99.99

-40%

Karl Lagerfeld Paris

Chukka Boots

From: SHOP SIMON

$224.93

Territory

Water Resistant Lace-up Ankle Boots

From: SHOP SIMON

Sizes:

12

$109.99

$169.99

-35%

CAT Footwear

Taupe Brown Leather Hiking Mid-cut Chukka Ankle Boots

From: SHOP SIMON

$181.99

$204.99

-11%

Vance Co.

Vance Co. Vaughn Lace-up Chukka Boot With 6 Mm Tru Comfort Foam™ And Three-eye Lace-up Closure

From: SHOP SIMON

Sizes:

11, 13

$49.99

Dockers

Esmond Dress Casual Lace Up Ankle Boot

From: SHOP SIMON

Sizes:

7, 8, 9, 12

$69.99

$95.00

-26%

Thomas & Vine

Elijah Wingtip Ankle Boot

From: SHOP SIMON

Sizes:

8, 9, 11

$59.99

$199.99

-70%

Territory

Titan 2.0 Cap Toe Ankle Boots

From: SHOP SIMON

Sizes:

10, 13

$64.99

Dolce & Gabbana

Ankle Boots

From: Italist

$566.67

Territory

Titan 2.0 Wide Width Cap Toe Ankle Boot

From: SHOP SIMON

Sizes:

8, 10, 11

$64.99

Maison Margiela

Tabi Split Toe Leather Ankle Boots

From: SHOP SIMON

$1,805.13

$2,013.67

-10%

Sturlini

Ankle Boots

From: Baltini

$320.00

$459.00

-30%

Brioni

Journey Suede Desert Boots

From: Neiman Marcus

Sizes:

9, 10, 11, 11.5, 12.5, 13

$1,195.00

CamperLab

Ankle Boots

From: SHOP SIMON

$412.75

$635.00

-35%

Thomas & Vine

Welch Wingtip Ankle Boot

From: SHOP SIMON

Sizes:

8, 9, 13

$59.99

Frye

Chukka Boots

From: SHOP SIMON

Sizes:

9, 12

$128.00

$188.00

-32%

Doucal's

Ankle Boots

From: Baltini

$383.00

$510.00

-25%

Red Wing

Ankle Boots

From: Baltini

$332.00

$462.00

-28%

Infinity Leather

Snakeskin Winklepicker Cowboy Leather Ankle Boots

From: SHOP SIMON

$218.99

Hugo Boss Ryan

Chelsea Boots

From: SHOP SIMON

Sizes:

8

$199.00

$260.00

-23%

Vance

Knit Chukka Boots

From: SHOP SIMON

Sizes:

8, 9, 10, 13

$49.99

Territory

_axel Ankle Boot With Distressed Coloring And Above Ankle Design_

From: SHOP SIMON

Sizes:

11

$84.99

$149.99

-43%

Etor

Ankle Cowboy Real Leather Wincklepickers Boots

From: SHOP SIMON

Sizes:

7, 8, 9, 10, 11, 12, 13

$223.75

$290.88

-23%

Reserved Footwear New York

Petrus Chukka Boots

From: SHOP SIMON

$73.00

$118.00

-38%

Vance

Thorpe Boots

From: SHOP SIMON

$109.99

Thomas & Vine

Samwell Plain Toe Ankle Boots

From: SHOP SIMON

Sizes:

8, 9, 11, 12

$54.99

Mustang

Water-resistant Chelsea Ankle Boots

From: SHOP SIMON

$127.99

$200.00

-36%

Stefano Ricci

Crocodile Leather Chukka Boots

From: Neiman Marcus

$8,200.00

Doucal's

Boot

From: Baltini

$434.00

$568.00

-24%

autry

Malga Mid Trekking Boots

From: SHOP SIMON

$311.11

$613.51

-49%

ELEVENTY

Suede High-top Boots

From: SHOP SIMON

$826.47

$1,035.87

-20%

V2 BRAND

Elastic Leather Boots

From: SHOP SIMON

$250.15

Territory

Drifter Ankle Boot

From: SHOP SIMON

Sizes:

8, 12, 13

$59.99

Giuseppe Zanotti

Zheno Boots

From: Giuseppe Zanotti

Sizes:

7, 8, 9, 10, 11

$475.00

$950.00

-50%

House Of Cavani

Suede Lace Up Chukka Boots

From: SHOP SIMON

$118.99

Kayland

Grand Tour Gtx Suede Boots

From: SHOP SIMON

$334.34

$427.01

-22%

our legacy

Calf Leather Camion Boots

From: SHOP SIMON

$963.83

Men's grey ankle boots