How To Style Chelsea Boots For Men

Everyone always talks about how Chelsea boots are versatile and timeless, and we completely agree! Chelsea boots date back all the way to the Victorian era, as sturdy walking and striding boots. Even Queen Victoria herself owned a satin pair for evening wear!

Part of the reason they continue to be so popular is their wide range of styles. Some distinctive styles include Australian Work Boots and Beatle boots.

The Chelsea boot became more popular in the swinging sixties and was closely associated with the King’s Road in London (hence the ‘Chelsea’ in Chelsea Boots). Designed with a pointed-toe shape, the style was embraced by The Beatles and frequently adopted by Mods, who paired the boots with tailored suits.

Need some inspiration? We've got you! Let us walk you through how to style Chelsea boots for men and what clothing works best with them.

What To Wear With Chelsea Boots

There are many ways you can style Chelsea boots, however, we're not sold on them being paired with shorts! Whether you have an evening event, or you're kicking back on a Sunday morning, there are plenty of ways to play about with your boots.

The main thing to note is that for a sleek look, we wouldn’t recommend tucking your trousers into your Chelsea boots. Instead, for a classic silhouette the hem (cuffed or not), should sit neatly just over the tops of your boots.

Jeans, chinos, straight-leg trousers, they all work! However, let us walk you through some more specifics...

Can You Wear Chelsea Boots with a Suit?

Of course! If you’re looking to add an extra element of style to an outfit for a special occasion, a smart Chelsea boot with an elegant leather construction works perfectly as a pair of dress shoes.

Black and Grey Suits – This style pairs well with a classic black Chelsea boot, as it creates a formal, monochromatic look. We love the smart versatility of R.M Williams' Gardener Boots with a darker suit. If you want to add a pop of colour to this outfit, you can add a colourful tie or pocket square!

Navy and Brown Suits – With these warm-toned suits, both black and brown boots would work well. It all depends on whether you want your boots to stand out as part of your outfit. Black tends to blend in more cohesively, whereas brown would make more of a statement.

Light Summer Suits – Camel and beige look fantastic with brown Chelsea boots. There is such a great range of brown tones boots that you can find, anything from deep browns to lighter tans. One of our favourite boots with a more extensive range of colours is the R.M. Williams Mens Comfort Craftsman Boots.

If you want a formal look but don't want to stretch as far as a suit, chinos are a great alternative. Add a shirt and you’ve got a smart and polished look!

How To Wear Chelsea Boots with Jeans

As the world has evolved, more casual outfits have become popular. We gravitate towards jeans more and more, but that doesn’t mean it always needs to be a relaxed weekend look. With jeans, there’s much more freedom on what colour boots match what outfits.

All styles of jeans work with Chelsea boots, slim-fit jeans, skinny jeans, wide leg and even cropped jeans. Let's dive more into that...

Smart Casual – For a smart casual look, there are plenty of options of colours and styles you can play around with. Similar to suits, our rule of thumb is that black jeans should pair with black boots. However, For white, blue or denim jeans, there are even more great choices.

Brown boots match perfectly with any shade of denim. White jeans can really go with any boot if you dress them well! Just throw on an Oxford shirt to complete your look and in the colder months, a v-neck or crew neck to stay warm.

Going Out – Using our tips above, style your night out with a nice shirt or neutral t-shirt. To elevate your look, add a complimentary blazer over the top, and make sure it matches the tones of your outfit! If that's too formal, a bomber jacket works just as well!

Relaxed – Blundstone boots are the perfect Chelsea boots for a relaxed feel. They work great with mid-wash or stone-wash jeans and a t-shirt for a casual look. If the weather isn’t the best, a flannel shirt or jumper over the top is a comfortable option. If Blundstone boots aren’t your style, we love these suede Clandon Chelsea boots from Chatham.

We’ve also written a more in-depth blog about styling your  Chelsea Boots with jeans which you might want to check out for more ideas! 

How To Wear Chelsea Boots with Skinny Jeans

You can style your skinny jeans much like any other type of jeans, the only real difference is how your jeans sit with your Chelsea Boots. We’ve mentioned several times that the hem of your jeans, cuffed or not, should sit over the top of your boots.

With skinny jeans, this isn’t always possible depending on how skinny they are. The main purpose of having your jeans like this is to avoid unflattering bunching at the ankles. So as long as there isn’t any bunching, tucking or cuffing of your jeans, the choice is up to you!

Ultimately, the way you dress and style yourself is totally up to you and your self-expression. Wear what makes you happy, and always rise to the challenge and try new styles! For any information regarding Chelsea boots, feel free to visit us in-store or call us at 01432 377089.