- View all in Category
- Men
- Chelsea Boots
- Clear all
- SALE
Blundstone
Chelsea Boots, male, , Size: 7 1/2 US Leather Ankle Boots
$178.00$223.00Shipping: Free over $100.00
7 1/2 US 8 1/2 US 8 US 11 US 12 USMore details Blundstone
Chelsea Boots, male, , Size: 9 1/2 US Premium Leather Pull-On Chelsea Boot
$209.00Shipping: Free over $100.00
9 1/2 US 10 1/2 US 10 US 11 1/2 US 11 USMore detailsPrada
Monolith leather Chelsea boots
$1,470.00Shipping: Free over $400.00
US 7 US 10 US 11 US 12 US 13More detailsPrada
Leather Chelsea boots
$1,450.00Shipping: Free over $400.00
US 7 US 7.5 US 8 US 8.5 US 9 US 10 US 10.5 US 11 US 12 US 12.5 US 13More details- SALE
Tod's
Chelsea Boots, male, , Size: 7 1/2 US Beatles Ankle Boots, Made in Italy
$550.00$825.00Shipping: Free over $100.00
6 1/2 US 7 1/2 US 7 US 8 1/2 US 8 US 9 USMore details - SALE
Camper
Chelsea Boots, male, , Size: 9 US Pix Ankle Boots
$150.00$190.00Shipping: Free over $100.00
7 US 8 US 9 US 10 US 11 USMore details - SALE
Hogan
Chelsea Boots, male, , Size: 10 US Vintage Chelsea Boots
$422.00$447.00Shipping: Free over $100.00
7 US 8 1/2 US 9 US 10 1/2 US 10 USMore details - SALE
Hogan
Chelsea Boots, male, , Size: 10 US Beatles Chelsea Boots, Wide Fit, Made in Italy
$414.00$437.00Shipping: Free over $100.00
8 1/2 US 8 US 9 1/2 US 9 US 10 US 11 USMore details Blundstone
Chelsea Boots, male, , Size: 10 1/2 US Antique Brown Leather Chelsea Boots
$257.00Shipping: Free over $100.00
9 1/2 US 10 1/2 US 10 US 11 USMore detailsManolo Blahnik
Brompton suede Chelsea boots
$945.00Shipping: Free over $400.00
US 7 US 8 US 8.5 US 9 US 9.5 US 10 US 11 US 11.5 US 12 US 14More detailsSACAI
Leather Chelsea boots
$1,260.00Shipping: Free over $400.00
US 7 US 8 US 9 US 10 US 11More detailsSaint Laurent
Wyatt suede Chelsea boots
$1,190.00Shipping: Free over $400.00
US 6 US 7 US 8 US 8.5 US 9 US 10More detailsErmenegildo Zegna
Leather Chelsea boots
$1,590.00Shipping: Free over $400.00
US 8 US 9 US 10 US 11 US 12 US 13More detailsJOHN LOBB
Lawry leather Chelsea boots
$2,500.00Shipping: Free over $400.00
US 7 US 8 US 8.5 US 9 US 9.5 US 10 US 11 US 11.5 US 13More detailsTom Ford
Patent leather Chelsea boots
$2,290.00Shipping: Free over $400.00
US 8.5 US 9.5 US 10.5 US 11.5 US 12.5 US 13.5More detailsTom Ford
Suede Chelsea boots
$1,490.00Shipping: Free over $400.00
US 7.5 US 8.5 US 9.5 US 10 US 10.5 US 11.5 US 12 US 12.5 US 13.5More detailsSaint Laurent
Wyatt leather Chelsea boots
$1,190.00Shipping: Free over $400.00
US 6 US 6.5 US 7 US 7.5 US 8 US 8.5 US 9 US 9.5 US 10 US 10.5 US 11 US 11.5More detailsManolo Blahnik
Delsa suede Chelsea boots
$995.00Shipping: Free over $400.00
US 7 US 8 US 8.5 US 9 US 9.5 US 10 US 10.5 US 11 US 12More detailsSaint Laurent
Wyatt leather Chelsea boots
$1,220.00Shipping: Free over $400.00
US 6 US 7 US 8 US 9 US 10 US 11 US 12More detailsChristian Louboutin
Urbino leather Chelsea boots
$1,195.00Shipping: Free over $400.00
US 6 US 7 US 8 US 9 US 10 US 11More detailsChristian Louboutin
Melon Spikes leather Chelsea boots
$1,495.00Shipping: Free over $400.00
US 6 US 7 US 8 US 9 US 10 US 11 US 12 US 13More detailsManolo Blahnik
Delsa suede Chelsea boots
$995.00Shipping: Free over $400.00
US 7 US 9 US 10 US 11 US 12 US 13More detailsJOHN LOBB
Masons leather Chelsea boots
$2,350.00Shipping: Free over $400.00
US 7 US 8 US 9 US 10 US 13More detailsBrunello Cucinelli
Suede Chelsea boots
$1,330.00Shipping: Free over $400.00
US 7 US 8 US 9 US 9.5 US 10 US 10.5 US 11 US 11.5 US 12 US 13More detailsAlexander McQueen
Trunk leather Chelsea boots
$1,390.00Shipping: Free over $400.00
US 7 US 8 US 9 US 10 US 11 US 12 US 13More detailsManolo Blahnik
Brompton suede Chelsea boots
$945.00Shipping: Free over $400.00
US 7 US 8 US 8.5 US 9 US 10 US 10.5 US 11 US 12 US 13 US 14More detailsSaint Laurent
Vadim leather Chelsea boots
$1,500.00Shipping: Free over $400.00
US 6 US 7 US 8 US 9 US 10 US 11 US 12More detailsChristian Louboutin
Alpinosol leather Chelsea boots
$1,425.00Shipping: Free over $400.00
US 7 US 8 US 9 US 10 US 11 US 12 US 13More detailsGEORGE CLEVERLEY
Jason leather Chelsea boots
$1,125.00Shipping: Free over $400.00
US 9 US 10 US 10.5 US 11 US 11.5 US 12 US 13 US 14More detailsRick Owens
Beatle Tractor suede Chelsea boots
$1,410.00Shipping: Free over $400.00
US 6 US 8 US 9 US 10 US 11 US 12 US 13More detailsChristian Louboutin
Alpinosol leather Chelsea boots
$1,295.00Shipping: Free over $400.00
US 7 US 8 US 9 US 10 US 11 US 12More detailsManolo Blahnik
Delsa suede Chelsea boot
$995.00Shipping: Free over $400.00
US 8 US 8.5 US 9 US 10 US 11 US 14More detailsErmenegildo Zegna
Suede Chelsea boots
$1,590.00Shipping: Free over $400.00
US 7 US 8 US 9 US 11 US 12More detailsSaint Laurent
Wyatt suede Chelsea boots
$1,190.00Shipping: Free over $400.00
US 6 US 7 US 7.5 US 8 US 8.5 US 9 US 10More detailsChristian Louboutin
Alpinosol suede Chelsea boots
$1,295.00Shipping: Free over $400.00
US 6 US 7 US 8 US 9 US 10 US 11 US 12 US 13More detailsCOMMON PROJECTS
Suede Chelsea boots
$660.00Shipping: Free over $400.00
US 7 US 8 US 9 US 10 US 11 US 12 US 13More detailsHogan
Chelsea Boots, male, , Size: 11 US Chelsea Boots
$437.00Shipping: Free over $100.00
7 US 8 1/2 US 8 US 9 1/2 US 10 USMore details- SALE
Dr. Martens
Chelsea Boots, male, , Size: 9 US Leather Chelsea Boots
$358.00$403.00Shipping: Free over $100.00
7 US 8 US 9 US 10 US 11 US 12 USMore details Emporio Armani
Chelsea Boots, male, , Size: 8 US Grained Leather Chelsea Boots
$481.00Shipping: Free over $100.00
7 US 8 US 9 1/2 US 9 US 10 1/2 US 10 US 11 US 12 USMore detailsDoucal's
Chelsea Boots, male, , Size: 7 US Chelsea Boots
$388.00Shipping: Free over $100.00
6 1/2 US 6 US 7 1/2 US 7 US 8 1/2 US 8 US 9 1/2 US 9 US 10 1/2 US 10 US 11 US 12 USMore detailsClarks
Chelsea Boots, male, , Size: 9 US Atticus LT Top Chelsea Boots
$135.00Shipping: Free over $100.00
7 1/2 US 8 US 9 1/2 US 9 US 10 USMore detailsDr. Martens
Chelsea Boots, male, , Size: 9 US Ambassador Leather Beatles Chelsea Boots
$195.00Shipping: Free over $100.00
7 US 8 US 9 US 10 US 11 US 12 USMore detailsDr. Martens
Chelsea Boots, male, , Size: 9 US 2976 YS Dark Crazy Horse Chelsea Boots
$195.00Shipping: Free over $100.00
7 US 8 US 9 US 10 US 11 US 13 USMore detailsDr. Martens
Chelsea Boots, male, , Size: 7 US 2976 Ambassador Chelsea Boots
$195.00Shipping: Free over $100.00
3 US 5 US 6 US 7 US 9 US 10 US 11 USMore details- SALE
Timberland
Chelsea Boots, male, , Size: 10 US Mid Chelsea Boot
$287.00$349.00Shipping: Free over $100.00
7 US 8 US 10 US 11 US 12 USMore details Blundstone
Chelsea Boots, male, , Size: 11 US Nubuck Leather Chelsea Boots
$238.00Shipping: Free over $100.00
8 1/2 US 8 US 9 US 10 1/2 US 10 US 11 USMore detailsBlundstone
Chelsea Boots, male, , Size: 10 1/2 US Ankle Boots Blu Noos
$248.00Shipping: Free over $100.00
6 US 7 US 9 1/2 US 10 1/2 US 10 US 12 USMore detailsBlundstone
Chelsea Boots, male, , Size: 3 1/2 US Chelsea 2032 Nero Boots
$268.00Shipping: Free over $100.00
3 1/2 US 4 1/2 US 4 US 5 1/2 US 6 USMore detailsBlundstone
Chelsea Boots, male, , Size: 9 US Chelsea Boots
$224.00Shipping: Free over $100.00
8 1/2 US 9 1/2 US 9 US 10 1/2 US 11 USMore detailsBlundstone
Chelsea Boots, male, , Size: 12 US Chelsea Boots
$223.00Shipping: Free over $100.00
6 US 7 US 8 1/2 US 10 1/2 US 10 US 12 USMore detailsBlundstone
Chelsea Boots, male, , Size: 9 US Ankle Boots Verde Noos
$212.00Shipping: Free over $100.00
7 US 8 US 9 US 10 1/2 US 11 US 12 USMore details- SALE
Tod's
Chelsea Boots, male, , Size: 11 US Suede Ankle Boots
$379.00$720.00Shipping: Free over $100.00
9 1/2 US 9 US 10 1/2 US 10 US 11 USMore details - SALE
Hogan
Chelsea Boots, male, , Size: 6 1/2 US Chelsea Boots Made in Italy
$414.00$437.00Shipping: Free over $100.00
6 1/2 US 8 US 9 1/2 US 11 USMore details - SALE
Green george
Chelsea Boots, male, , Size: 8 1/2 US Brogue Ankle Boots
$221.00$316.00Shipping: Free over $100.00
8 1/2 US 8 US 9 1/2 US 9 USMore details - SALE
Tod's
Chelsea Boots, male, , Size: 7 US Beatles boots made in Italy
$461.00$573.00Shipping: Free over $100.00
6 US 7 1/2 US 7 USMore details - SALE
Blundstone
Chelsea Boots, male, , Size: 8 US Classic Leather Boots
$243.00$270.00Shipping: Free over $100.00
4 US 8 US 11 USMore details Blundstone
Chelsea Boots, male, , Size: 4 1/2 US Stylish Classic Boots
$194.00Shipping: Free over $100.00
4 1/2 US 5 US 7 USMore details- SALE
Dr. Martens
Chelsea Boots, male, , Size: 7 US 2976 Chelsea Smooth Boots
$210.60$234.00Shipping: Free over $100.00
5 US 7 US 9 USMore details - SALE
Dior
Chelsea Boots, male, , Size: 9 US Classic Beatle Boots for Men
$722.00$1,164.00Shipping: Free over $100.00
7 US 8 US 9 US 11 US 12 USMore details - SALE
Céline
Cowboy Boots, male, , Size: 7 US Snake-Effect Chelsea Boots
$646.00$1,067.00Shipping: Free over $100.00
7 US 8 US 10 US 11 US 12 USMore details JOHN LOBB
Mason suede Chelsea boots
$2,350.00Shipping: Free over $400.00
US 7 US 8 US 11 US 12More detailsSaint Laurent
Wyatt suede Chelsea boots
$1,190.00Shipping: Free over $400.00
US 7 US 8 US 11 US 12More detailsDolce & Gabbana
Altavilla leather Chelsea boots
$1,045.00Shipping: Free over $400.00
US 7 US 9 US 10 US 12More details- SALE
Dr. Martens
Chelsea Boots, male, , Size: 10 1/2 US Leather Zip Chelsea Boots
$165.00$194.00Shipping: Free over $100.00
9 US 10 1/2 US 10 US 11 USMore details Panchic
Chelsea Boots, male, , Size: 12 US Beatle Suede Ankle Boots
$183.00Shipping: Free over $100.00
7 US 9 US 11 US 12 USMore details- SALE
Dr. Martens
Chelsea Boots, male, , Size: 3 US Smooth Ankle Boots
$358.00$403.00Shipping: Free over $100.00
3 US 4 US 5 US 6 USMore details Dr. Martens
Chelsea Boots, male, , Size: 5 US 2976 Ambassador Leather Chelsea Boots
$187.00Shipping: Free over $100.00
4 US 5 US 6 US 7 USMore detailsBlundstone
Chelsea Boots, male, , Size: 9 1/2 US Classics Chelsea Boots
$223.00Shipping: Free over $100.00
7 US 8 US 9 1/2 US 11 USMore detailsBlundstone
Chelsea Boots, male, , Size: 8 1/2 US Nubuck Chelsea Boot
$204.00Shipping: Free over $100.00
5 US 8 1/2 US 8 US 13 USMore detailsBlundstone
Chelsea Boots, male, , Size: 8 US Chelsea Boot
$202.00Shipping: Free over $100.00
7 US 8 US 10 1/2 US 10 USMore detailsBlundstone
Chelsea Boots, male, , Size: 8 US Classic Elastic Sided Boot
$238.00Shipping: Free over $100.00
8 1/2 US 8 US 9 1/2 US 9 USMore detailsBlundstone
Chelsea Boots, male, , Size: 9 1/2 US Classic Leather Beatles Ankle Boots
$194.00Shipping: Free over $100.00
7 1/2 US 9 1/2 US 10 US 12 USMore detailsBlundstone
Chelsea Boots, male, , Size: 8 1/2 US Waxed Suede Chelsea Boots
$204.00Shipping: Free over $100.00
7 1/2 US 8 1/2 US 8 US 10 USMore details- SALE
Berwick
Chelsea Boots, male, , Size: 9 US Mens Leather Ankle Boot - Art. 272 - UK 7.5
$231.00$262.00Shipping: Free over $100.00
8 1/2 US 8 US 9 US 12 USMore details Tod's
Chelsea Boots, male, , Size: 11 US Dark Flat Shoes with Logo
$728.00Shipping: Free over $100.00
7 1/2 US 7 US 8 1/2 US 9 1/2 US 9 US 10 US 11 USMore detailsAstorflex
Chelsea Boots, male, , Size: 12 US Leather Chelsea Flat Shoes
$306.00Shipping: Free over $100.00
8 US 9 US 10 US 11 US 12 USMore detailsTRICKERS
Chelsea Boots, male, , Size: 9 US Chelsea Flat Shoes
$660.00Shipping: Free over $100.00
8 1/2 US 8 US 9 1/2 US 9 US 10 US 11 USMore detailsTRICKERS
Chelsea Boots, male, , Size: 9 1/2 US Chelsea Flat Shoes Espresso
$660.00Shipping: Free over $100.00
8 1/2 US 8 US 9 1/2 US 9 US 10 1/2 US 10 US 12 USMore details- SALE
Tod's
Chelsea Boots, male, , Size: 7 US Beatles Leather Chelsea Boots
$506.00$631.00Shipping: Free over $100.00
6 US 7 1/2 US 7 USMore details - SALE
Doucal's
Chelsea Boots, male, , Size: 8 US Ankle Boots for Men
$262.00$374.00Shipping: Free over $100.00
7 US 8 US 12 USMore details Blundstone
Chelsea Boots, male, , Size: 10 US Flat Shoes Model 585
$257.00Shipping: Free over $100.00
7 US 10 US 11 USMore detailsDolce & Gabbana
Chelsea Boots, male, , Size: 8 1/2 US Leather ankle boots
$795.00Shipping: Free over $100.00
7 US 8 1/2 US 8 US 9 1/2 US 9 US 11 USMore detailsAllSaints
Chelsea Boots, male, , Size: 7 US Chelsea Boots Toby
$229.00Shipping: Free over $100.00
7 US 8 US 9 US 10 US 11 US 12 US 13 USMore details- SALE
Dolce & Gabbana
Chelsea Boots, male, , Size: 10 US Leather Chelsea Boots
$401.00$772.00Shipping: Free over $100.00
6 US 7 1/2 US 7 US 8 1/2 US 8 US 9 US 10 US 11 US 12 USMore details Moon Boot
Chelsea Boots, male, , Size: 10 US Snow Boots MB Luna Chelsea Suede
$207.00Shipping: Free over $100.00
8 US 10 US 11 US 12 US 13 USMore detailsTod's
Chelsea Boots, male, , Size: 8 1/2 US Winter Gommino Ankle Boot
$728.00Shipping: Free over $100.00
7 1/2 US 8 1/2 US 8 US 9 1/2 US 9 USMore details- SALE
Berwick
Chelsea Boots, male, , Size: 8 US Suede Ankle Boots
$228.00$291.00Shipping: Free over $100.00
7 US 8 1/2 US 8 US 9 1/2 US 9 US 10 1/2 US 10 US 11 USMore details Blundstone
Chelsea Boots, male, , Size: 10 US Rustic Chelsea Style Leather Boots
$235.00Shipping: Free over $100.00
4 US 5 US 6 US 7 US 8 US 9 US 10 US 11 US 12 USMore detailsFabi
Chelsea Boots, male, , Size: 7 US Chelsea Style Suede Boots
$378.00Shipping: Free over $100.00
7 US 8 US 9 US 11 US 12 USMore detailsHogan
Chelsea Boots, male, , Size: 8 US Suede Chelsea Ankle Boots
$437.00Shipping: Free over $100.00
7 1/2 US 7 US 8 1/2 US 8 US 9 1/2 US 9 US 10 1/2 US 10 US 11 USMore details- SALE
Blundstone
Chelsea Boots, male, , Size: 3 US Classic Leather Chelsea Boots
$210.60$234.00Shipping: Free over $100.00
3 US 4 1/2 US 4 US 5 1/2 US 8 US 10 1/2 US 10 US 11 US 13 USMore details - SALE
TRICKERS
Chelsea Boots, male, , Size: 12 US Shoes
$631.00$665.00Shipping: Free over $100.00
8 1/2 US 8 US 9 1/2 US 9 US 10 1/2 US 11 US 12 US 13 USMore details - SALE
Fabi
Chelsea Boots, male, , Size: 7 US Suede Chelsea Boot with Zip Closure
$339.00$368.00Shipping: Free over $100.00
7 US 8 1/2 US 8 US 9 US 10 US 11 USMore details Dolce & Gabbana
Chelsea Boots, male, , Size: 12 US Boots with Rubber Sole
$772.00Shipping: Free over $100.00
6 US 7 US 8 US 9 1/2 US 9 US 10 US 11 US 12 USMore details- SALE
Blundstone
Chelsea Boots, male, , Size: 10 1/2 US Classic Chelsea Boots
$193.00$225.00Shipping: Free over $100.00
8 1/2 US 8 US 9 1/2 US 10 1/2 US 10 US 11 US 12 US 13 USMore details Green george
Chelsea Boots, male, , Size: 10 US Leather Beatles Shoes
$396.00Shipping: Free over $100.00
7 US 8 US 9 US 10 US 11 USMore detailsANTICA CUOIERIA
Chelsea Boots, male, , Size: 7 US Chelsea Boots Classic Style
$180.00Shipping: Free over $100.00
7 US 8 US 9 US 10 US 11 USMore detailsANTICA CUOIERIA
Chelsea Boots, male, , Size: 12 US Chelsea Boots Classic Style
$180.00Shipping: Free over $100.00
7 US 8 US 9 US 10 US 11 US 12 USMore detailsHogan
Chelsea Boots, male, , Size: 8 US Leather Ankle Boots Swallow-Tailed
$511.00Shipping: Free over $100.00
8 US 9 1/2 US 10 1/2 US 10 US 11 USMore detailsSANGIORGIO
Chelsea Boots, male, , Size: 7 US Suede Boots for Men
$135.00Shipping: Free over $100.00
7 US 8 US 9 US 10 US 11 USMore details
Not enough men choose to wear ankle boots, are you going to be one of them? Find out why and how on Fashiola. Men’s Chelsea Boots are hands-down one of the most attractive looks – so why don’t more men wear them? Chelsea boots are not limited to being worn with a pair of skinny jeans either, straight leg jeans or chinos are perfectly fine to combine with some Chelsea boots. If you want to make your look more casual out, swap out the traditional leather look for some suede – if you’re brave enough to wear them throughout the winter, you’re perfect for the style.