How to Wear Chelsea Boots: 6 Sleek, Sublime Ways to Style the Slip-On Classics
StyleBeloved by legendary rockers and A-list actors alike, these time-tested dress boots remain a sure bet for almost any occasion.By Jeremy FreedNovember 13, 2024Photographs: Getty Images; Collage: Gabe ConteSave this storySaveSave this storySaveAll products are independently selected by our editors. If you buy something, we may earn an affiliate commission.It’s time you learned how to wear Chelsea boots properly. See, there are a lot of great boots in the world, from yellow rubber puddle stompers to dressy numbers made from shell cordovan and lizard skin, all of which arguably deserve a place in your shoe closet. The one you’re likely to wear more than any other, however, is the humble Chelsea boot. Combining the ruggedness of a work boot, the easy-wearing comfort of a loafer, and the sleek lines of an oxford, these perennially stylish slip-ons have been a go-to footwear choice for nearly 200 years.Alongside Sherlock Holmes, Charles Darwin, and those goofy bicycles with the giant front wheel, you can thank the Victorian era for bestowing the Chelsea boot on the world. The first pair of Chelseas are said to have been made as a walking and riding boot for Queen Victoria (who apparently wasn’t a big fan of laces) in the 1830s. Being something of a trendsetter, the style quickly caught on and the Chelsea boot has remained popular and relatively unchanged ever since.What has changed, however, is how people wear their Chelsea boots. Where once they were paired only with tailored wear like suits, nowadays you'd be hard-pressed to find a fit your Chelseas wouldn't work with. They look incredible with a leather jacket and jeans, with a button-down and wide-leg work pants, with a turtleneck and flowy trousers. Here are six foolproof ways to pull 'em off to help get you started.Level UpAustin Butler, 2022 Samir HusseinA Chelsea with a stacked (a.k.a. Cuban) heel promises to lift both your height and your fashion cred.Embrace EleganceJeff Goldblum, 2024 Steve GranitzA sleek black Chelsea with a mirror shine makes for a fresh take on black tie.Rock OutThe Rolling Stones, 1965 Evening Standard/Getty ImagesMost PopularGQ RecommendsThe Best Chelsea Boots Are Tall, Dark, and HandsomeBy Gerald OrtizShoesThe Best Dress Shoes for Industry Titans, Layabout Heirs, and Everyone BetweenBy Gerald OrtizStyleThe 68 Best Red-Carpet Looks of All Time (and What You Can Learn From Them)By Yang-Yi GohAs style inspo goes, you could do worse than the Rolling Stones circa 1965. Mick's sport coat and knit polo rig, in particular, wouldn't look a hair out of place in 2024.Go WestJustin Theroux, 2024 Dimitrios Kambouris/Getty ImagesCan Chelsea boots be a little bit country? You can bet the ranch on it, pardner.Hit the SkiesJimi Hendrix, 1967 Mirrorpix/Getty ImagesMost PopularGQ RecommendsThe Best Chelsea Boots Are Tall, Dark, and HandsomeBy Gerald OrtizShoesThe Best Dress Shoes for Industry Titans, Layabout Heirs, and Everyone BetweenBy Gerald OrtizStyleThe 68 Best Red-Carpet Looks of All Time (and What You Can Learn From Them)By Yang-Yi GohThe Chelsea's slip-on design makes it a perfect choice for the TSA line—whether you also choose to pack an abundance of silk scarves is entirely up to you.David Beckham, 2022 GothamA pair of rough-and-tumble suede Chelseas are the perfect anchor for your Canadian tuxedo.Our Favorite Chelsea BootsFeeling inspired? Great. There's a whole world of incredible Chelsea boots out there for you to explore. Here are four killer options we adore.R.M. WilliamsGardener Whole-Cut Leather Chelsea Boots$539 Mr PorterJacques SolovièreMark Boots$546 Todd SnyderJ.M. WestonChelsea Boots$1,420 NordstromBeckett SimononPreston Chelsea Boots$259 Beckett SimononHow to Wear Chelsea Boots FAQWhy are they called Chelsea boots?AccordionItemContainerButtonLargeChevronFollowing its first golden era in the 19th century, the Chelsea hit its stride once again in the 1960s on the swinging streets of London, where it was adopted by the likes of Mick Jagger and Jean Shrimpton (a.k.a. the world’s first supermodel). One of the best places to pick up a pair of these stylish slip-ons was the fashionable London shopping district of Chelsea, and the name stuck.How should Chelsea boots fit?AccordionItemContainerButtonLargeChevronBecause of their laces-free design, Chelseas will fit a bit differently than other styles of boot. Look for a little bit of wiggle room in the toes, a snug (but not tight) fit around the widest part of the foot, and—most importantly—no gap between your heel and the back of the boot.Are Chelsea boots business casual?AccordionItemContainerButtonLargeChevronYes, but it depends on the boot. Lug-soled work boots like Blundstones have a more rugged look, making them better suited for casual days and weekends. If you’re going for business casual, look for a sleeker pair with thinner soles and a bit more polish.What pants are best with Chelsea boots?AccordionItemContainerButtonLargeChevronWhat’ve you got? The beauty of Chelsea boot
All products are independently selected by our editors. If you buy something, we may earn an affiliate commission.
It’s time you learned how to wear Chelsea boots properly. See, there are a lot of great boots in the world, from yellow rubber puddle stompers to dressy numbers made from shell cordovan and lizard skin, all of which arguably deserve a place in your shoe closet. The one you’re likely to wear more than any other, however, is the humble Chelsea boot. Combining the ruggedness of a work boot, the easy-wearing comfort of a loafer, and the sleek lines of an oxford, these perennially stylish slip-ons have been a go-to footwear choice for nearly 200 years.
Alongside Sherlock Holmes, Charles Darwin, and those goofy bicycles with the giant front wheel, you can thank the Victorian era for bestowing the Chelsea boot on the world. The first pair of Chelseas are said to have been made as a walking and riding boot for Queen Victoria (who apparently wasn’t a big fan of laces) in the 1830s. Being something of a trendsetter, the style quickly caught on and the Chelsea boot has remained popular and relatively unchanged ever since.
What has changed, however, is how people wear their Chelsea boots. Where once they were paired only with tailored wear like suits, nowadays you'd be hard-pressed to find a fit your Chelseas wouldn't work with. They look incredible with a leather jacket and jeans, with a button-down and wide-leg work pants, with a turtleneck and flowy trousers. Here are six foolproof ways to pull 'em off to help get you started.
Level Up
A Chelsea with a stacked (a.k.a. Cuban) heel promises to lift both your height and your fashion cred.
Embrace Elegance
A sleek black Chelsea with a mirror shine makes for a fresh take on black tie.
Rock Out
As style inspo goes, you could do worse than the Rolling Stones circa 1965. Mick's sport coat and knit polo rig, in particular, wouldn't look a hair out of place in 2024.
Go West
Can Chelsea boots be a little bit country? You can bet the ranch on it, pardner.
Hit the Skies
The Chelsea's slip-on design makes it a perfect choice for the TSA line—whether you also choose to pack an abundance of silk scarves is entirely up to you.
A pair of rough-and-tumble suede Chelseas are the perfect anchor for your Canadian tuxedo.
Our Favorite Chelsea Boots
Feeling inspired? Great. There's a whole world of incredible Chelsea boots out there for you to explore. Here are four killer options we adore.
How to Wear Chelsea Boots FAQ
Why are they called Chelsea boots?
Following its first golden era in the 19th century, the Chelsea hit its stride once again in the 1960s on the swinging streets of London, where it was adopted by the likes of Mick Jagger and Jean Shrimpton (a.k.a. the world’s first supermodel). One of the best places to pick up a pair of these stylish slip-ons was the fashionable London shopping district of Chelsea, and the name stuck.
How should Chelsea boots fit?
Because of their laces-free design, Chelseas will fit a bit differently than other styles of boot. Look for a little bit of wiggle room in the toes, a snug (but not tight) fit around the widest part of the foot, and—most importantly—no gap between your heel and the back of the boot.
Are Chelsea boots business casual?
Yes, but it depends on the boot. Lug-soled work boots like Blundstones have a more rugged look, making them better suited for casual days and weekends. If you’re going for business casual, look for a sleeker pair with thinner soles and a bit more polish.
What pants are best with Chelsea boots?
What’ve you got? The beauty of Chelsea boots is their versatility, and they can look great with just about everything from jeans and cords to tuxedo pants.
Are Chelsea boots in style?
Perpetually. The Chelsea boot has risen and fallen in popularity over the last 200 years, but its combination of comfort, versatility, and style keeps people coming back decade after decade. Are there trendier boots out there? Perhaps. But you won’t find many with more staying power.
