How to Style Chelsea Boots

Chelsea boots have been a favoured choice for centuries, with a history that harks back to the Victorian era.  There's something to be said about the steadfast popularity of this time-honoured classic. 

Traditionally crafted with flat soles, rounded toes, and iconic  stretch side panels, Chelsea boots are famed for their androgynous appeal. Worn by both women and men, their practicality and versatility make them a wardrobe staple.

A good pair of ankle boots are like a best friend for your feet. Are classic  black and brown Chelsea boots  hard to beat? Yes. Do refreshed retro designs make our heart skip? Yes! Bold and chunky Chelsea boots have been brought into the spotlight and they're going nowhere. 

Whether you're reaching for timeless tailoring or prefer daring design to make your mark, the question remains: How do you style Chelsea boots? From subtle updates to bold new silhouettes, we've created a need-to-know guide so you can invest in boots that deliver instant impact. 

What to wear with women’s Chelsea boots?

Trust us when we say the Chelsea is the true hero of the capsule wardrobe. You can wear Chelsea boots with jeans, tailored trousers, skirts, and dresses too. To cut a long story short, they’ll go with pretty much everything you already own.

Our Clemenzia boots demonstrate the Chelsea boot’s versatility. An elongated form of the familiar silhouette, its  pared-back qualities make them entirely adaptable to the occasion, stepping you from dressed down days, to smart casual, and on to glamourous evening events. 

How to wear Chelsea boots with jeans

Chelsea boots and jeans, the unofficial wardrobe of autumn/winter. We’ll refrain from uttering the words ‘style basics’, but this dynamic duo promise to lay the foundations for many a great outfit. 

It’s important to stick to a few style rules when wearing your Chelseas with jeans. Pay attention to your hemlines, if they sit above your ankle it will shorten the appearance of your legs. Instead, go for a pair of high-waisted jeans and add a turn up, so the hems sit above your boots. Lengthening the appearance of your leg and showing your boots off in all their glory? Win-win. 

For a casual outfit, tan or brown Chelsea boots are the perfect match for blue jeans and stone-washed denims, whereas white or black boots are great to wear with a darker pair of jeans, for a smarter look.

How to wear Chelsea boots with dresses

With many iterations of the Chelsea boot, the ways to style Chelsea boots with dresses are infinite, so it really is a matter of personal choice. If you’re a fan of classic style, brown Chelseas are the perfect match for knee length dresses, whether worn with bare legs or layered up with woolly tights. A timeless investment that will work from season to season.

Chunky Chelsea boots finish off feminine silhouettes with added edge. Equipped with larger-than-life soles, stomper boots are practical, comfortable, and ultra-flattering, perfect for day-to-night dressing. Chunky lug soles are a cool contrast to pretty silky slips for an easy (and comfy) day look. Who says you need a pair of heels to look glamorous?

How to wear heeled Chelsea boots

Smart-casual styling can be a minefield. If you're looking for workwear outfits, a pair of heeled Chelseas will spruce up the monotony of your tailored separates, plus they’ll layer up with tights and dresses.

For us, black ankle boots are never a bad choice when it comes to versatility, the essential foundation for a smart and put-together look. Go for sleek silhouettes with tapered toes and practical block heels that will keep you feeling comfortable and supported throughout the day (and the night).

What to wear with men’s Chelsea boots?

Thanks to their timeless shape and design, Chelsea boots are a simple and sophisticated footwear choice for men of all ages. From cool and casual options to slick and smart styles, you'll have these classics on constant rotation. 

Chelsea boots are ideal for wearing with suits, especially in the cooler months. Opt for a slick leather pair, with a close-fitting shape and tapered toes as this will lend a sophisticated polish to your tailoring. 

When wearing Chelsea boots with your smart attire, it’s vital to pay attention to the cut and colour of your suit, go for slim-fit trousers that are cropped to either sit neatly above your boots or just above your feet, avoiding any creases of fabric around the ankles.

For autumn and winter, experiment with layering textures and colours by mixing and matching your separates, with checked shirts and less formal jackets, as demonstrated by Yele King.

What to wear with brown Chelsea boots?

Not only reserved for the office, a pair of brown Chelsea boots slip effortlessly into your casual wardrobe. The key is to look for a boot with a more relaxed silhouette, like the rounded toes and rugged finish of our Debden boots. 

Nubuck leathers in palettes of tans and browns lend an at-ease elegance to any look. From weekends at your local, to lavish city breaks, Chelseas are true style chameleons.