How to Wear Chelsea Boots

A staple of any well dressed man’s collection, a pair Chelsea boots are a timeless classic that deserve a spot on every shoe rack. 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, we have all you need to know.

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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 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 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 that’ll work with every scenario. How about some brown leather boots with a grey suit? This will give you that effortless smart look, as London Chelsea boots with a suit is one of the most signature looks of them all.

If you prefer a classic navy or blue tailored suit, try pairing them with a dark brown leather Chelsea boot. The contrast of the brown against blue is a failsafe, complementary combo that’ll elevate any ensemble. As seen below, always leave your trousers sitting over your Chelsea boots, as this makes for a cleaner, smarter look. Nailing a brown Chelsea boot outfit can be a difficult task, but once you’ve got it right there will be no stopping you from rocking the look day in, day out. The same goes for if you’re wondering how to wear heeled Chelsea boots. 

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Brown Chelsea boots with a grey suit is work ready attire
PHOTO CREDIT: Pinterest

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How to Wear Ankle Boots with Jeans

If you’re keeping the look dressed down, wear your boots with jeans paired with a T-shirt and casual jacket. For the boots themselves, go for either a suede or matte look to keep things a little more laid back. If you’re going for a slightly smarter look, a high shine or patent leather boot will do the trick.

When it comes to jeans, black suede Chelsea boots for men will go with a wide array of styles, 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 right style points.

Just because you’re 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 to pull the whole look together. A pair of The Idle Man black Chelsea boots will make you more than ready for a smarter setting.

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.

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A dark brown Chelsea boot goes well with a navy suit
PHOTO CREDIT: Pinterest

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What to Look for When Buying Chelsea Boots

As with any shoes, make sure they’re 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.

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, whereas 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. A black version is probably the most versatile and best Chelsea boot for men.

How to Wear Chelsea Boots

  • Although the Chelsea boot is incredibly versatile it’s worth noting; always wear them with your jeans or trousers outside and over the boot.
  • A cuban heeled Chelsea boot gives a rockstar-esque look: sartorially daring but classically timeless. This is a true Beatles vibe.
  • Men’s suede Chelsea boots are perfect for a slightly casual look, with faux suede offering a broader range of colours, the boot will look great with skinny jeans, trousers or a suit.
  • Simply mix the Chelsea boot with jeans and a T-shirt for a superior smart casual ensemble.
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the versatile Chelsea boot is perfect for a range of occasions
PHOTO CREDIT: Pinterest

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 for going out in town. Keep your colours matching and you’ll be able to do what you want with them. Mix and match different T-shirts, or shirts and pair them with jeans or trousers. Whatever your favourite outfit is, there’s a Chelsea boot to match. It just goes to show that when it comes to the Chelsea boot, the world is your oyster.

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