How to Wear Chelsea Boots

From knee highs to ankle grazers, wellingtons to western styles, there is no such thing as a bad boot. However, with its effortless adaptability and iconic status, there may 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 it’s their elastic side panel that sets them apart from other types of ankle boot.

The beautiful, adaptable Chelsea boot has a pretty interesting history which dates back to Victorian times. The Victorians are known for their fabulous fashion choices, so we’re hardly surprised that it was them who first strode forth in this style.

It was actually Queen Victoria’s cobbler himself who was the one to create the boot, which was initially called a Paddock Boot and mostly worn by riders. 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 fast 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 had 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 infamous 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. Today the Chelsea boot is celebrated by some of our favourite modern-day icons, from Kate Moss to Victoria Beckham.

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 fabulously versatile, leather Chelsea boots are a brilliant addition to any outfit, and are undoubtedly the best Chelsea boots for women. 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, it goes with just about any outfit. Since suede is harder to clean, we recommend saving your suede Chelsea boots for those special occasions – or at least drier days!

Chelsea boots outfits

What to wear with Chelsea boots for women

A beautiful pair of leather Chelsea boots will look just as amazing with jeans as they do with a floaty floral 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 pulled off by Helen Mirren as it is Alexa Chung, so we don’t want to hear any age-related excuses!

What to wear with Chelsea boots for men

For men, well-crafted Chelsea boots will give you endless outfit possibilities. They are so adaptable that no wardrobe should ever be without a pair, whether you opt for suede brown, which will give you more of a country gent look, or black leather for the ultimate rockstar 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 a fab alternative to Oxford shoes, brogues and loafers, Chelsea boots can even work well with a smart suit—perfect for if you have any winter weddings coming up!


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 2021 - 2022?

They’ve been around since the 1950s, so it’s safe to say that Chelsea boots have stood the test of time. They’re still very much in style in 2021-2022, and we can’t see that changing anytime soon.

Do you tuck jeans into Chelsea boots?

Chelsea boots look best when the hem of your jeans finishes just at the top of your boot—so some rolling might be required! Generally speaking, jeans shouldn’t be tucked into Chelsea boots, though if you’re wearing super skinny jeans, that rule no longer applies.

Like a best friend, a good pair of Chelsea boots will see you through many years of your life – so you’ll really 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.