How to Wear Chelsea Boots

A staple of any well-dressed man’s collection, Chelsea boots are a timeless classic that deserve pride of place in any man’s footwear wardrobe. No matter your age, size, or personal style; there’s a boot for every occasion. If you’re wondering how to approach putting together a Chelsea boot supported ensemble, read on for more!

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How to Wear Chelsea Boots

So what are Chelsea boots? They’re one of the most versatile boots for men. The laceless style can be worn with many outfits and are perfect for a range of seasons and occasions. Whether it’s a formal, casual or somewhere in between, the Chelsea boot can easily be dressed to suit the occasion.

How to Wear Chelsea Boots with Suits

While most would think of an Oxfords, brogues or loafers when considering suiting suitable footwear, the Chelsea boot is another great option that’s often more suitable than you’d think. Coming in a wide range of different colours, materials and finishes there’s something to work with every scenario. How about some brown leather boots with a grey suit? This will give you that ‘London look’ as the London Chelsea boot with a suit is, after all, the most signature look of them all.



If you prefer a classic navy or blue tailored suit, try pairing them with a brown leather Chelsea boot. The contrast of the brown against blue is a failsafe, complimentary combo that’ll elevate any ensemble. As seen below, always leave your trousers sitting over Chelsea boots as this makes for a clean, smarter look. Nailing a brown Chelsea boot outfit can be a hard task but once you’ve got it right they’ll be no stopping you from rocking the look day in day out.



How to Wear Ankle Boots with Jeans

If you’re keeping the look dressed down, wear with jeans paired with a T-shirt and casual jacket. For the boots themselves, go for either suede or matte look to keep things a little more laid back but if you’re going for a slightly smarter look a high shine or patent leather boot will do the trick. Regardless of where you plan on wearing them, men’s Chelsea’s are a great addition to any men’s shoe collection.

Black suede Chelsea boots for men will go with a wide array of clothing, however try not to pair them with too much brown as it’s always best to keep the colours similar. Wearing men’s boots with jeans will give you that effortlessly cool, casual, ‘rockstar’ look and when paired with a leather jacket you’ll have hit all the style points.



Just because your opting to pair your boots with jeans doesn’t mean the look has to be overtly casual. To smarten up, keep things simple with understated or pastel colour choices. Often seen on style icon Kanye West, mix a pair of grey jeans with a plain smart shirt and add a classic leather biker jacket if you want to pull the whole look together. A pair of black Chelsea boots or brown Chelsea boots will make you more than ready for a smarter setting. Kanye West’s Chelsea boot ‘addiction’ has him hitting all the right style notes and he has paired them with near enough every outfit due to their classic and simple style.


How to Wear a Cuban Heel Chelsea Boot

The famous Beatle Boot was a great take on the Chelsea boot – it’s a Chelsea with a Cuban heel that’s both sartorially daring and classically timeless AND gives that rockstar look. But most importantly, when considering how to wear heeled Chelsea boots or Cuban heeled boots, it’s imperative that you ensure your trousers are the correct length. So, when out shopping for the best trousers, take the shoes you’re going to be wearing them with along with you, this way you can be sure that your trousers are at the right length and you avoid any unintentional ankle swinging scenarios.

Beatles Boots


The Rules for Wearing Men’s Chelsea Boots

There are no hard and fast rules that are unique to Chelsea boots. Of course, you want to make sure that your colours don’t clash, but other than that, the main thing to remember is that generally, the leg of your trousers should sit over the top of the boot. Still, don’t forget, you’ve paid money for those boots – so don’t hide them, your trousers or jeans should sit just over the top.

Stacking your jeans is very popular way to show off your all important shoes, but you don’t really want to overly do that with your Chelsea boots and trouser combination: you can stack your trousers over the boots but make sure its minimal and don’t deteriorate away from the boot itself.

mens chelsea boots looks street style


Guide to Buying Chelsea Boots

If you want to add some Chelsea boots to your collection, there are a few things to consider when buying them. The visual aspect is obviously important because you want something that you’re immediately drawn to. It’s also important to take the manufacturer and material composition into account as this will be a good indicator of their value for money.

Who Makes the Best Chelsea Boots?

Finding the best Chelsea boots for men needs a lot of thought as there are so many out there. Pretty much every designer that makes men’s footwear out there has a Chelsea boot or similar style in their collection. Depending on your budget, you can always find a pair of Chelsea boots for men that’ll suit your personal sense of style, as well as the occasion for which you want them for. As with everything, you get what you pay for, but that doesn’t necessarily mean you need to break the bank to get a good pair.

Obviously, if you spend £15 on a pair of boots, you can probably expect that their life span will be a little shorter than that of a £150 pair. In all honesty, it’s typically better to invest a little more with footwear as spending an extra £50 can really make the difference.

chelsea boots on foot
PHOTO CREDIT: Individualism


What to Look for When Buying Chelsea Boots

As with any shoes, make sure they are going to fit well. It’s not worth saving yourself a tenner just to have the shoes rub on your heels and toes, as that would be a complete waste. A decent sole is something to look for when buying your new boots, this will help to increase the life and will stop them looking worn out as soon as you start wearing them everyday. A cobbler will be able to repair a good sole, so when it eventually wears out, you can can save your shoes and some cash.

Whether you’re going for leather, suede or a synthetic version of the boot, ensure they are made of the good stuff as you don’t want them falling apart as soon as you buy them. While we’re on the subject of good material, make sure you consider when and where you’ll be wearing them. Suede will not be good for the wet weather but will look smarter in the evenings, leather is an all rounder and will be suitable for both the autumn and winter months. If you do go for suede you can buy shoe protector and cleaner so your shoes will look newer for longer. So, when you go to buy Chelsea boots, there may be more to consider than you think but most importantly think about your own personal style and how they’ll fit in with the rest of your wardrobe.



Further Reading: History of the Chelsea Boot

A boot this versatile and popular has definitely got some history to it, The Chelsea boot has been in production for over 150 years. Unlike workhouses and sewage in the Thames, the Chelsea Boot is one Victorian thing that is still with us in the 21st century and we couldn’t be happier. Plus, they’re still as fresh and modern today as they ever have been.

They were first created by Queen Victoria’s own personal boot maker, J. Sparkes Hall, who used the newly invented vulcanised rubber, along with elastic, to make the boot easy to put on and take off, using the loop at the back to help get leverage. Of course, over time, they have been adapted, and you can buy them with slightly built up heels (Beatle Boot), pointed toes, fancier wingtip styles, and lacing (not quite Chelsea boots). The classic Chelsea, however, is lace-free and simple in its style and was adopted by the mod culture in the 1950’s. These mod Chelsea boots were worn with tailored trousers, a jacket and a classic white shirt.

By the time the 1960s rolled around, The Beatles, like everything they touched, turned them into the hottest footwear around. So what exactly are Chelsea boots? While they’d been around for far longer, the ‘Chelsea boot’ derive its name from being associated where The Beatles originally had them commissioned. They were London fashion boots, and that was hot whether you were from New York, Paris, or Burnley. These ‘rockstar boots’ were a Beatles signature which were usually leather Chelsea boots worn with a suit both on stage and off stage.

The Beatles Boot

How to Wear Chelsea Boots

  • Although the Chelsea boot is incredibly versatile it’s worth noting; always wear them with your jeans / trousers outside the boots.
  • Try to match them with your belt for a cleaner, put together look.
  • A cuban heeled chelsea boot gives a rockstar-esque look: sartorially daring but classically timeless.
  • Men’s Suede chelsea boots are perfect for a more casual look, with faux suede allowing for a broader range of colours that look great with skinny jeans.
  • Simply mix with jeans and a T-shirt for a superior smart casual ensemble.
mens chelsea boots suede black

On That Note

Chelsea boots have been a firm favourite for the last 150 years, and you just cannot go wrong with them. They’re perfect for every occasion, whether you want them for a formal event, for work, or just going out in town. Keep your colours matching well, and you can do what you want with them: mix and match different t-shirts, or shirts; pair them with jeans or trousers. All the time you have a favourite outfit, there’s a Chelsea boot that will match. It just goes to show that when it comes to The Chelsea Boot: The World is your oyster.


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