How to Wear Chelsea Boots

How to wear a chelsea boot | What to wear with Chelsea boots with jeans - Pinterest title

The most versatile shoe in a men’s wardrobe is a Chelsea boot.

I’m a sucker for them! They’re comfortable, smart and there are so many styles available which gives our style more individuality! In this post I’m sharing my tips for finding a good Chelsea boot and what you can wear with them!

Building a core wardrobe is all about versatility, but it doesn’t need to start and finish with the clothing – you need core shoes too. To me, the Chelsea boot is the most versatile shoe, the equivalent of a leather jacket. It’s something you can slip on (literally, there are no laces!) and wear out at night or during the day and look smart in.


Men’s boots come in all different shapes and finishes, but a classic Chelsea is a slim fitting ankle boot, often in brown or black leather. It has a piece of elastic around the side of the ankle bone and often has a wooden or leather sole.


When you work in a role that is business casual or smart casual, the chelsea boot is a perfect work option. It can be worn with jeans or chinos and a button up or blazer and later worn with a knitted jumper on a casual day out. You can wear a chelsea boot with your suit in winter, but the best shoe worn with your suit is a brogue or oxford.


To answer this question simply, the only thing you definitely wouldn’t want to wear a pair of Chelsea boots with is shorts or cropped pants, because they’re high-cut. What you can wear them with is jeans, chinos and even a more relaxed suit. Most of the time, these boots come in different shades of brown or black leather. The more casual will always be brown and is perfect for pairing with denim or a chino, the black looks smart with a dark pant but can be worn both day and night.

Choose a belt that matches your boots for a more put together look or forgo the belt and wear a tee and bomber for a more casual look. These are the perfect shoes to wear for those smart casual nights out, going to the pub or a relaxed restraint for dinner and work well with coats in winter.

The next decider for choosing a boot is to choose between a smooth leather, suede or nubuck!


Smooth leather Chelsea boots are the most common to find in stores. They’re soft and change colour with age and can be worn in most weather. It’s important to waterproof these, even though they’re regular leather, they’ll last so much longer if you do!


Texture is an underappreciated part of men’s style, in my opinion. Suede Chelsea boots are the perfect way to add some rugged depth to your outfit. Suede is much more delicate than nubuck, meaning you should be careful not to wear them on grass and overly wet days. Even if it’s not raining, it’s best to waterproof these after every one to two wears.


Nubuck leather looks like suede but is more durable and more suitable for winter conditions, like wet weather. You’ll look super cosy in these with a pair of relaxed jeans and a knitted sweater, but you’ll be even cosier if you waterproof them!


When you buy chelsea boots, they should be a snug fit. The shoe will stretch over time and with no way to tighten it, you’ll have a longer lasting shoe if you focus on ensuring the heel is firm and your toes are about a thumb space away from the front. Have your chelsea boots toped (pronounced toe-peed) by a cobbler, this will reinforce the sole and help them to last longer. You’ll also find yourself less likely to slip on the carpet which is a bonus!

How do you wear your chelsea boots? Let me know in the comments!

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