Shop Men's Dress Ankle Boots

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$140.00
Steve Madden Men's Duke Chelsea Boot Black Leather 11
Amazon.com
37
Free shipping
$140.00
Steve Madden Men's Duke Chelsea Boot Black Leather 11
Amazon.com
37
$134.95
$149.95
Florsheim Midtown Plain Toe Men's Boot, 9 3E US, Black
Amazon.com
244
Free shipping
10% off
$134.95
$149.95
Florsheim Midtown Plain Toe Men's Boot, 9 3E US, Black
Amazon.com
244
$109.95
Florsheim Men's, Chalet Cap Toe Boot
Amazon.com
124
Free shipping
$109.95
Florsheim Men's, Chalet Cap Toe Boot
Amazon.com
124
$44.99
Men's Retro Leather Business Ankle Boots
Nocini
$44.99
Men's Retro Leather Business Ankle Boots
Nocini
$199.95
Steve Madden Men's Santana Ankle Boots - Brown - Size 7 - Leather
Steve Madden
$199.95
Steve Madden Men's Santana Ankle Boots - Brown - Size 7 - Leather
Steve Madden
$102.00
$120.00
Nunn Bush® Karnak Men's Leather Plain Toe Ankle Boots, Size: 14, Brown Crazy Horse
Kohl's
3
Free shipping
15% off
$102.00
$120.00
Nunn Bush® Karnak Men's Leather Plain Toe Ankle Boots, Size: 14, Brown Crazy Horse
Kohl's
3
$149.99
Florsheim Midtown Plain Toe Boot | Men's | Cognac | Size 12 | Boots
DSW
286
Free shipping
$149.99
Florsheim Midtown Plain Toe Boot | Men's | Cognac | Size 12 | Boots
DSW
286
$114.99
Stacy Adams Santos Boot | Men's | Black | Size 8 | Boots
DSW
2K+
Free shipping
$114.99
Stacy Adams Santos Boot | Men's | Black | Size 8 | Boots
DSW
2K+
$149.99
Florsheim Duke Bicycle Toe Boot | Men's | Cognac | Size 10 | Boots
DSW
Free shipping
$149.99
Florsheim Duke Bicycle Toe Boot | Men's | Cognac | Size 10 | Boots
DSW
Free shipping
$55.99
Handmade Black Ankle Boots For Men - Comfortable & Stylish Leather Footwear
Nocini
$55.99
Handmade Black Ankle Boots For Men - Comfortable & Stylish Leather Footwear
Nocini
$102.00
$120.00
Nunn Bush® Karnak Men's Leather Moc Toe Ankle Boots, Size: 8.5, Brown Crazy Horse
Kohl's
6
Free shipping
15% off
$102.00
$120.00
Nunn Bush® Karnak Men's Leather Moc Toe Ankle Boots, Size: 8.5, Brown Crazy Horse
Kohl's
6
$80.00
Dockers® Esmond Men's Ankle Boots, Size: 10.5, Brown
Kohl's
Free shipping
$80.00
Dockers® Esmond Men's Ankle Boots, Size: 10.5, Brown
Kohl's
Free shipping
$59.99
$64.47
Men's Brown And Black Chelsea Boots With Brogue Detailing, Genuine Faux Leather Slip-On Ankle Boots For Business, Weddings And Smart Casual Wear
LightInTheBox
$59.99
$64.47
Men's Brown And Black Chelsea Boots With Brogue Detailing, Genuine Faux Leather Slip-On Ankle Boots For Business, Weddings And Smart Casual Wear
LightInTheBox
$59.99
$64.47
Men's Brown Wingtip Chelsea Boots With Brogue Detailing, Elegant Ankle Style For Gentlemen, Perfect For Business, Weddings And Formal Occasions
LightInTheBox
1
$59.99
$64.47
Men's Brown Wingtip Chelsea Boots With Brogue Detailing, Elegant Ankle Style For Gentlemen, Perfect For Business, Weddings And Formal Occasions
LightInTheBox
1
$261.75
$550.00
Allen Edmonds Landon Cap-Toe Boot Boots In Black Leather, Size 11.0 D
Allen Edmonds
52% off
$261.75
$550.00
Allen Edmonds Landon Cap-Toe Boot Boots In Black Leather, Size 11.0 D
Allen Edmonds
$54.99
$58.68
Men's Black Crocodile Pattern Faux Leather Chelsea Boots - Elegant Slip-On Ankle Boots For Formal And Business Wear
LightInTheBox
6
$54.99
$58.68
Men's Black Crocodile Pattern Faux Leather Chelsea Boots - Elegant Slip-On Ankle Boots For Formal And Business Wear
LightInTheBox
6
$1,350.00
Bottega Veneta Lug Chelsea Ankle Boot - Black - Man - 7,5
Bottega Veneta
Free shipping
$1,350.00
Bottega Veneta Lug Chelsea Ankle Boot - Black - Man - 7,5
Bottega Veneta
Free shipping
$48.99
$100.00
St. John's Bay Mens Rutland Flat Heel Chelsea Boots | Black | Regular 11 | Boots Chelsea Boots | Memory Foam|Memory Foam Insole | Valentine's Day
JCPenney
23
51% off
$48.99
$100.00
St. John's Bay Mens Rutland Flat Heel Chelsea Boots | Black | Regular 11 | Boots Chelsea Boots | Memory Foam|Memory Foam Insole | Valentine's Day
JCPenney
23
$150.00
Florsheim Midtown Plain Toe Zipper Boots Men's Dress Zip Boots Cognac : 8 m (D), Leather
Zappos
329
$150.00
Florsheim Midtown Plain Toe Zipper Boots Men's Dress Zip Boots Cognac : 8 m (D), Leather
Zappos
329
$319.00
Grain Leather Lace Up Boots - Walnut Brown Size 10 By Charles Tyrwhitt
Charles Tyrwhitt
$319.00
Grain Leather Lace Up Boots - Walnut Brown Size 10 By Charles Tyrwhitt
Charles Tyrwhitt
$270.00
Mens Square Toe Ankle Boots 7.5 / Black
parahombreusa
$270.00
Mens Square Toe Ankle Boots 7.5 / Black
parahombreusa
$52.50
$75.00
Deer Stags Mens Rockland Block Heel Chelsea Boots | Brown | Regular 10 1/2 | Boots Chelsea Boots | Memory Foam|Comfort|Memory Foam Insole
JCPenney
7K+
Free shipping
30% off
$52.50
$75.00
Deer Stags Mens Rockland Block Heel Chelsea Boots | Brown | Regular 10 1/2 | Boots Chelsea Boots | Memory Foam|Comfort|Memory Foam Insole
JCPenney
7K+
$44.99
$100.00
J. Ferrar Mens Blake Flat Heel Chelsea Boots | Black | Regular 10 1/2 | Boots Chelsea Boots | Memory Foam | Valentine's Day
JCPenney
40
55% off
$44.99
$100.00
J. Ferrar Mens Blake Flat Heel Chelsea Boots | Black | Regular 10 1/2 | Boots Chelsea Boots | Memory Foam | Valentine's Day
JCPenney
40
$99.99
$129.99
Joseph Abboud Men's Alan Cap Toe Inside Zipper Ankle Boots Cognac - Size: 10 D-Width
Men's Wearhouse
23% off
$99.99
$129.99
Joseph Abboud Men's Alan Cap Toe Inside Zipper Ankle Boots Cognac - Size: 10 D-Width
Men's Wearhouse
$129.99
$154.99
Florsheim Men's Chalet Cap Toe Boots (Black Crazy Horse Leather) - Size 9.5 m
Famous Footwear
160
Free shipping
16% off
$129.99
$154.99
Florsheim Men's Chalet Cap Toe Boots (Black Crazy Horse Leather) - Size 9.5 m
Famous Footwear
160
$49.99
Quilted Lined Ankle Boots For Men - Supportive Warmth & Comfort
Nocini
$49.99
Quilted Lined Ankle Boots For Men - Supportive Warmth & Comfort
Nocini
$155.00
Florsheim Lodge Cap Toe Lace-Up Boots Men's Shoes Brown Crazy Horse : 10.5 m (D), Leather
Zappos
90
$155.00
Florsheim Lodge Cap Toe Lace-Up Boots Men's Shoes Brown Crazy Horse : 10.5 m (D), Leather
Zappos
90
$120.00
$150.00
Florsheim Men's Midtown Zip Boots, Black, 10.5M, Leather
belk
2K+
Free shipping
20% off
$120.00
$150.00
Florsheim Men's Midtown Zip Boots, Black, 10.5M, Leather
belk
2K+
$270.00
Mens Black Square Toe Ankle Boots 11 / Black
parahombreusa
$270.00
Mens Black Square Toe Ankle Boots 11 / Black
parahombreusa
$150.00
Men's Florsheim Midtown Plain Toe Zipper Dress Boots Dress 10.5 Black
Scheels
2K+
$150.00
Men's Florsheim Midtown Plain Toe Zipper Dress Boots Dress 10.5 Black
Scheels
2K+
$74.99
$99.99
Deer Stags Men's Garfield Supro Inside Comfort Dress Chukka Boots (Black) - Size 13.0 m
Famous Footwear
25% off
$74.99
$99.99
Deer Stags Men's Garfield Supro Inside Comfort Dress Chukka Boots (Black) - Size 13.0 m
Famous Footwear
$362.00
Men's Los Altos Boots Genuine Ostrich Higher Heel Paw Black Dress Boot Ankle Dress Style For Man Black / 7 Standard / D / Medium
parahombreusa
$362.00
Men's Los Altos Boots Genuine Ostrich Higher Heel Paw Black Dress Boot Ankle Dress Style For Man Black / 7 Standard / D / Medium
parahombreusa
$134.99
$149.99
Florsheim Men's Midtown Plain Toe Zip Boots (Cognac Leather) - Size 10.0 D
Famous Footwear
281
Free shipping
10% off
$134.99
$149.99
Florsheim Men's Midtown Plain Toe Zip Boots (Cognac Leather) - Size 10.0 D
Famous Footwear
281
$165.00
Florsheim Duke Men's Dress Zip Boots Black Cavello : 10.5 D (M), Leather
Zappos
977
$165.00
Florsheim Duke Men's Dress Zip Boots Black Cavello : 10.5 D (M), Leather
Zappos
977
$89.99
Men's Deer Stags Rockland Chelsea Boot In Black Size 10
Shoe Carnival
5K+
$89.99
Men's Deer Stags Rockland Chelsea Boot In Black Size 10
Shoe Carnival
5K+
$56.99
Bruno Marc Men Busines Dress Oxford Boots Classic Ankle Boot Cap Lace Up Leather Lined Boots Warner-2 Black Size 10
Walmart
3
$56.99
Bruno Marc Men Busines Dress Oxford Boots Classic Ankle Boot Cap Lace Up Leather Lined Boots Warner-2 Black Size 10
Walmart
3
12 Handsome Dress Boots in Every Budget to Upgrade Your Footwear
12 Handsome Dress Boots in Every Budget to Upgrade Your Footwear
Feb 13, 2023
Men's HealthMaverick Li
How to Wear Ankle Boots With Practically Every Outfit You Own
How to Wear Ankle Boots With Practically Every Outfit You Own
2 months ago
realsimple.com
35 High Ankle Boots Outfit Ideas for Winter 2024 | Men's Fashion
8:30
35 High Ankle Boots Outfit Ideas for Winter 2024 | Men's Fashion
6.1K viewsDec 10, 2023
YouTubeRed Wolf Fashion Guide
10 Stylish Men's Fall Outfits | How To Style Boots 2021
7:23
10 Stylish Men's Fall Outfits | How To Style Boots 2021
491.5K viewsOct 14, 2021
YouTubeAlex Costa
7 Essential Boot Styles For Men & Where to Get Them
9:14
7 Essential Boot Styles For Men & Where to Get Them
Jan 8, 2020
gentlemanwithin.com
Ultimate Guide To Buying Men's Dress Boots | Different Boot Styles | Chelsea | Chukka | Lace-Up
8:43
Ultimate Guide To Buying Men's Dress Boots | Different Boot Style…
914.8K viewsOct 15, 2016
YouTubeReal Men Real Style
Stylish Ankle Boots for Men This Fall
0:08
Stylish Ankle Boots for Men This Fall
3.1K views3 months ago
TikTokalainuer0m7
Rogue Studs Handmade Men’s Black Triple Monk Strap Boots | G…
3 months ago
etsy.com
5:37
How To Style Men's Dress Boots/How To Wear Men's Dress …
73.6K viewsSep 7, 2017
YouTubeThe Style O.G.
11:16
Mens Ankle Boots | Outfits To Wear With Cowboy Boots
4K viewsOct 29, 2021
YouTubePhatkat Collections
12:46
ULTIMATE Guide To Men’s Boots | Mens Fashioner | Ashley Weston
405.7K viewsOct 7, 2022
YouTubeMens Fashioner
11:31
8 Different Ways To Style Boots | Best Boots For Men | Men’s Boot…
139.6K viewsFeb 25, 2020
YouTubeHe Spoke Style
11:24
Complete Men's Boot Guide | Mens Fashioner | Ashley Weston
127.6K viewsNov 12, 2021
YouTubeMens Fashioner
10:03
12 Ways to Style Chelsea Boots (Fall/Winter) | Outfit Ideas | Men's …
2.2M viewsNov 24, 2019
YouTubeOne Dapper Street
7:30
How To Wear Chelsea Boots/How To Style Men's Chelsea Boots
101.6K viewsNov 3, 2018
YouTubeThe Style O.G.
10:58
Men's Boots Outfits That Women LOVE! | Mens Fashioner | Ashley …
209.8K viewsOct 11, 2022
YouTubeMens Fashioner
7:26
8 Outfits Styling Men's Boots for Fall & Winter
54.5K viewsDec 7, 2024
YouTubeOne Dapper Street
4:30
How to Wear Boots in the Summer | Men’s Fashion | Clarks Desert, Do…
152.3K viewsJun 26, 2019
YouTubeOne Dapper Street
6:15
How to PROPERLY Wear Chelsea Boots || Men's Fashion Fall 2020 || …
195K viewsNov 3, 2020
YouTubeGent's Lounge
6:57
How To Style Dress Boots | Men's Dress Boots
143.5K viewsNov 24, 2020
YouTube40 Over Fashion
9:03
Styling these ASOS men's heeled boots into 5 different looks
8.4K viewsDec 5, 2021
YouTubeNelson a La Mode
9:47
How To Wear Men’s Boots 101 - 5 Best Boot Styles: Chukka, Chelse…
285.7K viewsDec 26, 2016
YouTubeGentleman's Gazette
9:02
12 Casual Chelsea Boots Outfits | Men’s Fall & Winter Inspiration
119.5K viewsNov 20, 2021
YouTubeOne Dapper Street
6:47
9 Best DRESS BOOTS for Men
68K viewsSep 17, 2022
YouTubeBootSpy
15:14
How To Buy The PERFECT Boot (10 Boot Styles & How To Wear)
121.1K viewsOct 13, 2022
YouTubeReal Men Real Style
7:18
How to Style Boots This Fall | Men's Chelsea, Combat and Dress Boot I…
2.4M viewsOct 16, 2018
YouTubeOne Dapper Street
1:10
The Best Ways to Wear Men's Ankle Boots : Men's Boots & Denim Fas…
118K viewsJun 12, 2014
YouTubeehowbeauty
13:04
The 10 Best Dress Boots for Men | Balmorals, Chelseas, Custom, an…
105.5K viewsSep 3, 2023
YouTubeStridewise
3:10
How Do Ankle, Mid-calf, And Knee-high Boots Differ? - The Sharp Dre…
4 views3 months ago
YouTubeThe Sharp Dressed Gent
15:00
9 Boot Styles You Need To Know & The 2 You Must Own!
53.7K viewsSep 14, 2023
YouTubeReal Men Real Style
See more videos
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Shop Men's Dress Ankle Boots

Sponsored
About our ads
$140.00
Steve Madden Men's Duke Chelsea Boot Black Leather 11
Amazon.com
37
Free shipping
$140.00
Steve Madden Men's Duke Chelsea Boot Black Leather 11
Amazon.com
37
$134.95
$149.95
Florsheim Midtown Plain Toe Men's Boot, 9 3E US, Black
Amazon.com
244
Free shipping
10% off
$134.95
$149.95
Florsheim Midtown Plain Toe Men's Boot, 9 3E US, Black
Amazon.com
244
$109.95
Florsheim Men's, Chalet Cap Toe Boot
Amazon.com
124
Free shipping
$109.95
Florsheim Men's, Chalet Cap Toe Boot
Amazon.com
124
$44.99
Men's Retro Leather Business Ankle Boots
Nocini
$44.99
Men's Retro Leather Business Ankle Boots
Nocini
$199.95
Steve Madden Men's Santana Ankle Boots - Brown - Size 7 - Leather
Steve Madden
$199.95
Steve Madden Men's Santana Ankle Boots - Brown - Size 7 - Leather
Steve Madden
$102.00
$120.00
Nunn Bush® Karnak Men's Leather Plain Toe Ankle Boots, Size: 14, Brown Crazy Horse
Kohl's
3
Free shipping
15% off
$102.00
$120.00
Nunn Bush® Karnak Men's Leather Plain Toe Ankle Boots, Size: 14, Brown Crazy Horse
Kohl's
3
$149.99
Florsheim Midtown Plain Toe Boot | Men's | Cognac | Size 12 | Boots
DSW
286
Free shipping
$149.99
Florsheim Midtown Plain Toe Boot | Men's | Cognac | Size 12 | Boots
DSW
286
$114.99
Stacy Adams Santos Boot | Men's | Black | Size 8 | Boots
DSW
2K+
Free shipping
$114.99
Stacy Adams Santos Boot | Men's | Black | Size 8 | Boots
DSW
2K+
$149.99
Florsheim Duke Bicycle Toe Boot | Men's | Cognac | Size 10 | Boots
DSW
Free shipping
$149.99
Florsheim Duke Bicycle Toe Boot | Men's | Cognac | Size 10 | Boots
DSW
Free shipping
$55.99
Handmade Black Ankle Boots For Men - Comfortable & Stylish Leather Footwear
Nocini
$55.99
Handmade Black Ankle Boots For Men - Comfortable & Stylish Leather Footwear
Nocini
$102.00
$120.00
Nunn Bush® Karnak Men's Leather Moc Toe Ankle Boots, Size: 8.5, Brown Crazy Horse
Kohl's
6
Free shipping
15% off
$102.00
$120.00
Nunn Bush® Karnak Men's Leather Moc Toe Ankle Boots, Size: 8.5, Brown Crazy Horse
Kohl's
6
$80.00
Dockers® Esmond Men's Ankle Boots, Size: 10.5, Brown
Kohl's
Free shipping
$80.00
Dockers® Esmond Men's Ankle Boots, Size: 10.5, Brown
Kohl's
Free shipping
$59.99
$64.47
Men's Brown And Black Chelsea Boots With Brogue Detailing, Genuine Faux Leather Slip-On Ankle Boots For Business, Weddings And Smart Casual Wear
LightInTheBox
$59.99
$64.47
Men's Brown And Black Chelsea Boots With Brogue Detailing, Genuine Faux Leather Slip-On Ankle Boots For Business, Weddings And Smart Casual Wear
LightInTheBox
$59.99
$64.47
Men's Brown Wingtip Chelsea Boots With Brogue Detailing, Elegant Ankle Style For Gentlemen, Perfect For Business, Weddings And Formal Occasions
LightInTheBox
1
$59.99
$64.47
Men's Brown Wingtip Chelsea Boots With Brogue Detailing, Elegant Ankle Style For Gentlemen, Perfect For Business, Weddings And Formal Occasions
LightInTheBox
1
$261.75
$550.00
Allen Edmonds Landon Cap-Toe Boot Boots In Black Leather, Size 11.0 D
Allen Edmonds
52% off
$261.75
$550.00
Allen Edmonds Landon Cap-Toe Boot Boots In Black Leather, Size 11.0 D
Allen Edmonds
$54.99
$58.68
Men's Black Crocodile Pattern Faux Leather Chelsea Boots - Elegant Slip-On Ankle Boots For Formal And Business Wear
LightInTheBox
6
$54.99
$58.68
Men's Black Crocodile Pattern Faux Leather Chelsea Boots - Elegant Slip-On Ankle Boots For Formal And Business Wear
LightInTheBox
6
$1,350.00
Bottega Veneta Lug Chelsea Ankle Boot - Black - Man - 7,5
Bottega Veneta
Free shipping
$1,350.00
Bottega Veneta Lug Chelsea Ankle Boot - Black - Man - 7,5
Bottega Veneta
Free shipping
$48.99
$100.00
St. John's Bay Mens Rutland Flat Heel Chelsea Boots | Black | Regular 11 | Boots Chelsea Boots | Memory Foam|Memory Foam Insole | Valentine's Day
JCPenney
23
51% off
$48.99
$100.00
St. John's Bay Mens Rutland Flat Heel Chelsea Boots | Black | Regular 11 | Boots Chelsea Boots | Memory Foam|Memory Foam Insole | Valentine's Day
JCPenney
23