How to wear Chelsea Boots

From knee highs to ankle grazers, wellingtons to western styles, there’s no such thing as a bad boot. But with its effortless adaptability and iconic status, there might be one that we love just that little bit more than the others. All hail the fabulously versatile Chelsea boot!

What are Chelsea boots?

Chelsea boots are typically made from leather, with a rounded toe and a low heel. But their elastic side panel sets them apart from other types of ankle boots.

The beautiful, adaptable Chelsea boot has an interesting history that dates back to Victorian times. In an era known for it’s remarkable fashion, we’re hardly surprised that it’s here that the Chelsea boot was introduced to the nation.

It was Queen Victoria’s cobbler, Sparks Hall, who created the boot, which was initially called a Paddock Boot and mostly worn by riders. The point of the initial boot was to create a shoe that would be easy to wear and take off. And that gave birth to the always-in-fashion Chelsea boot. Who wouldn’t want to wear a shoe that was originally designed for royalty?

Why are they called “Chelsea” boots?

Brace yourself for this one, as our story involves none other than avant-garde pioneers!

Back in the 1950s, the Chelsea boot became a style staple for a band of trend-setting trailblazers. They claimed the shoe as their own, and it wasn’t long before they coined the name “Chelsea boot” after the area of London they lived in.

Way back before Instagram was a thing, it was the writers, artists, aristocrats, and musicians who were the influencers of the time - and it wasn’t long before they’d caused a stir in the fashion community. Before long, newspapers and magazines began to write about the famous Chelsea boot, kick-starting the Chelsea boot trend.

Proudly worn by superstars everywhere, including The Beatles and Andy Warhol, the Chelsea boot quickly became an icon - one that could be worn by anyone. For those with a daring streak, they replaced the brogue in the 1960s workplace, while for many they were the perfect style for a night out.

The good news for us mere mortals is that you don’t have to be a fashion icon to wear them. While they were a little slower to catch on, women’s Chelsea boots are now as popular as men’s Chelsea boots, and there are endless ways to rock them!

Chelsea boots materials

Leather Chelsea boots

Sleek, smooth, and versatile, leather Chelsea boots are a brilliant addition to any outfit and are the most popular Chelsea boots for women for good reason. Leather is the ideal material for the Chelsea boot since it’s super easy to keep clean and lasts for many years. Popular colours include black, brown, and tan, but bright colours can also be fun!

Suede Chelsea boots

The suede Chelsea boot has the power to take any outfit from day to night, and like the leather Chelsea boot, this pair goes with just about any outfit. Since suede is a bit trickier to clean, we recommend saving your suede Chelsea boots for those special occasions - or at least drier days!

How to wear Chelsea boots

Chelsea boots can be worn as an alternative to many shoe styles including brogues, trainers and loafers. They can be worn to the office and even on special occasions like weddings. Read on for our guide to the best outfits to pair with Chelsea boots.

What to wear with Chelsea boots - Outfits for women

For that easy-chic casual look, a beautiful pair of leather Chelsea boots will look just as amazing with jeans as they do with a midi skirt. And while you can pair Chelsea boots with most things, if you want to really nail the iconic look, try completing your outfit with a leather biker jacket. This stylish look is as easily rocked by Helen Mirren as it is by Kendall Jenner - and these versatile boots can be styled with jeans and a roll neck jumper for that stylish (but still super-warm!) look.

For a more formal ensemble, Chelsea boots look sharp with a suit or with a straight black and wool coat, making them the perfect footwear for the office.

What to wear with Chelsea boots - Outfits for men

For men, well-crafted Chelsea boots give you endless outfit possibilities. They’re so adaptable that no wardrobe should ever be without a pair, whether you opt for brown suede, which will give you more of a country gent look, or black leather for an edgier vibe.

Team them with a T-shirt and jeans for a dressed-down look or wear your boots to work by pairing them with chinos. Since they make an ace alternative to Oxford shoes, brogues, and loafers, Chelsea boots even work well with a smart suit-perfect for if you have any winter weddings coming up.

How to wear Chelsea boots with jeans

Styling Chelsea boots with jeans is easy thanks to the versatility of this timeless shoe. Chelsea boots look best when the hem of your jeans finishes just at the top of your boot—so some rolling might be required! This means they are a good fit for your frayed hem jeans and cropped jeans. We think that jeans look best when they’re not tucked into Chelsea boots, though if you’re wearing super skinny jeans, that doesn’t apply.


What is the difference between Chelsea boots and ankle boots?

While Chelsea boots resemble the classic ankle boot in many ways, it’s their elastic side panel that makes them stand out from the rest. Find tips and inspiration on how to wear ankle boots.

Why are Chelsea boots so popular?

Chelsea boots are so popular because they look great with pretty much every outfit, last for a long time, and never seem to go out of fashion. We all love a versatile shoe!

Are Chelsea boots still in style 2022-2023?

They’ve been around since the 1950s, so it’s safe to say that Chelsea boots have stood the test of time. They’re definitely still in style in 2022-2023, and we can’t see that changing any time soon. So, take advantage of this timeless shoe style and grab yourself a pair of Chelsea boots from our versatile collection.

Like a best friend, a good pair of Chelsea boots will see you through many years of your life - so you’ll be getting your money’s worth! Looking for more boot inspiration? Check out our guide to the best autumn boots, or read all about the latest autumn shoe trends.

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