outfit inspiration

How To Style Chelsea Boots

Thu 07 Dec 23

Like tea and crumpets, Chelsea boots are a British classic, and have even played a part in one of the most famous subcultural movements ever.

Their versatility and blending of comfort and style make them a timeless footwear choice for men and everyone else.

Dating back to 1850s Victorian England, the design and invention of the Chelsea boot is attributed to J. Sparkes-Hall, boot maker to Queen Victoria, who he ensured was a number one fan of the shoe.

Despite their association with riding, these boots were made for walking, and that’s just what they did.


Their big moment in the limelight arrived with the addition of the Cuban heel in the 1960s, when they caught the eyes of a little band called The Beatles.

The group wore them with collarless grey jackets and suit trousers to create iconic matching uniforms. It’s not surprising that the sartorially obsessed mod groups picked up on the trend, adding them to the style code

These sleek and ankle-high boots have since become a staple, but not only for preppy style lovers- Kanye West has been spotted in them, and they are so versatile they were even used for storm troopers’ footwear in the original Star Wars trilogy.


Chelsea boots come in 3 types: a dressier version with pointier toes, a casual variant made with heavier materials and chunkier soles, and lastly a hybrid design that combines elements of both.  

Whether you're aiming for a casual, smart-casual, or even a slightly formal look, these boots will get the job done.

Their elasticated slides make them so easy and quick to slip on that they will become your go to footwear.

In this guide, we'll explore four looks you can emulate with Chelsea boots, ensuring you step out with confidence and panache every time.


While Chelsea boots are inherently casual, you can still incorporate a sharp, high-quality pair into semi-formal outfits. Suit trousers or chinos in a navy-blue pair well with a dark brown, well-polished leather shoe, or mix black and grey tones together.

Add a white t-shirt or a well-fitted sweater and complete the look with a wool coat or a long waterproof option like a trench coat.

This combination takes on formal with effortless ease, making it suitable for a variety of occasions, from dinner party to business meeting (most office wear is more relaxed nowadays). You could even go for the full tailored suit for a contemporary twist on traditional formalwear.

In this case a pointier shoe makes more sense, and make sure the trousers have a slight break to cover the top of the boots, maintaining a polished appearance. 


Here you can opt for chunkier soled Chelsea boots and matt or shiny leather finishes. Get yourself some work trousers like the Carhartt WIP double knee pant and a belt so they don’t hang low or look baggy.

Layer a hoodie or t-shirt with fleece jacket or a shirt jacket and consider adding a functional crossbody bag to tie everything together.


Channel Robert De Niro’s grungy look in ‘Taxi Driver’ with well-fitted jeans (but not skinny, never skinny!), brown Chelsea boots and a matching bomber jacket.

Both leather and suede boots work well for casual looks, but a darker monochromatic colour scheme will take you towards the sleeker side of things. It can be as simple as a cable knit sweater and black cuffed jeans, or brown chinos and a black t-shirt.

It's a simple yet effective way to look good without trying too hard. 

Rock and Roll

Embrace the Chelsea boot’s history with a modern take on the rock and roll look. All you need is a leather jacket, a dark sweater or t-shirt and light-coloured straight leg jeans, or even bootcut if you want to look like Elvis.

But avoid wide leg jeans because the whole shoe will be covered, and what’s the point in that? A simple chain necklace will add some extra edge to the look. 

Enhance your Chelsea boots ensemble with carefully chosen accessories. Consider adding a leather belt that complements the colour of your boots.

A watch or bracelet can add a touch of personality. Just be mindful not to overdo it – simplicity often enhances the overall look.

An important thing to note is your sock choice. Chelsea boots look great with no-show socks for a clean and contemporary vibe.

However, in colder weather or with formal attire, opt for dress socks that match the colour of your trousers to create a seamless look. If your socks peep through below your cuffed trousers, then a fun pattern never hurt anybody!

Chelsea boots are a versatile addition to any man's wardrobe, providing adaptable styling possibilities for both casual outings and formal events. Remember to pay attention to the details, experiment with different looks, and most importantly, wear them with confidence.

If you want to elevate your fashion game without overdoing it, then mastering the art of styling Chelsea boots will undoubtedly get you there.


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