How Men Can Wear Chelsea Boots With Style

A staple of menswear, find out how to style this footwear
Sam Brady

The Chelsea boot is a fashionable and versatile piece of footwear for men that lends itself well to a range of outfits. Not all men are blessed with a room full of clothes and accessories, so the necessity to be able to wear items more than once is crucial. To the extreme, this is a core practice for anyone looking to build a minimalist wardrobe. But, in the simplest of terms, it just makes sense for us to spend our hard-earned cash on footwear that works well with different outfits. Which is the reason we love to wear Chelsea boots.

If you are looking for boots that aren't just billed for casual weekends and can be dressed up or down at a whim, then Chelsea boots have your back. To give yourself the greatest chance of wear, we recommend a black or dark brown version in leather. But, we also hold a suede version of the same colours in similar regard when it comes to sartorial versatility.

What Are Chelsea Boots?

If you are new to the game, Chelsea boots are a stylish and unique piece of footwear constructed with an elastic or vulcanised rubber attachment at the sides. They come constructed without laces and can easily slide on and off your foot. They typically extend to the ankle and have a small tab at the back to make pulling them on easier.

The name "Chelsea" is rumoured to come from the Chelsea region of London where the style was trendy among men and women in the 50s and 60s.

Style Tips for Chelsea Boots

Despite the Chelsea boot being a mainstay of men's fashion for decades, it is still not fully embraced. We can only put this down to the lack of understanding when styling this type of footwear. With just a few pointers in the right direction, I'm sure more men will be confident enough to wear this boot style more often.

To make sure your Chelsea boots are working well within your outfit there are a few sartorial guidelines we recommend you follow.

  • Leather Chelsea boots are preferred as they work with both suits and jeans
  • Dark brown or black is a versatile and timeless colour choice
  • Never tuck your trousers into your boots
  • Your trouser length should fall over the top of your boots
  • Keep the boot leather polished if wearing with a suit
  • Use suede protector before you wear suede boots for the first time

Leather Chelsea Boots

Leather options are the most popular type of Chelsea boots available. They have a sophisticated, slim silhouette and work well with smart and casual attire.

Think of your leather Chelsea boots as you would any other dress shoe. Style your leather boots with formal trousers either as a part of a suit or as a smart casual outfit. But, pay attention to the fit. The Chelsea boot looks its best when the trouser is not too loose. You want a slim silhouette from the trouser through the boot, with the trouser length sitting around two inches over the ankle of the boot.

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Suede Chelsea Boots

The other option is a suede material. They are much the same as leather Chelsea boots regarding fit but appear slightly more casual/smart casual than their leather counterparts.

It is incredibly important whenever you buy suede footwear that you protect it. Due to the nature of the material, it is very easy to stain. Therefore a spray protector should be applied before you wear them for the first time.

We would recommend styling a brown pair with an untucked slim-fit shirt and charcoal jeans. For a black suede Chelsea boot, partner with black jeans.

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How To Wear Chelsea Boots With A Suit

men wearing chelsea boots with suits

Partnering Chelsea boots with a suit can evoke a 60s feel for menswear. Much owing to this period being an era when the footwear style really took off. So, if you want to get your Mick Jagger on, then take a note of how to pair your colours correcty.

Navy Suit

Some men might be a stickler for the outdated style rule that blue and black shouldn't be worn together. But we believe that if you get the tones right then they can be an ideal style match. If in doubt, stick to a darker brown though trying a black boot with navy suit could be just the ticket.

Grey Suit

The colour palette of grey and black is a tried and tested combination. Often men will only use a black oxford or brogue shoe in partnership. Why not revamp your formal footwear options by introducing some black Chelsea boots into the mix.

How To Wear Chelsea Boots Smart Casual

chelsea boots smart casual

By removing the tie and mixing blazer and trousers in complimentary colours and materials you can take a formal look and make it appear slightly more casual.

Though when this is attempted result, men tend to fall into the formal camp with their footwear. The smarter silhouette of the Chelsea boot can transcend through both styles and means men opting for an alternative to a brogue or oxford don't have to go too casual with a trainer.

Depending on whether men want to air on the more formal or casual side of the scale then can play with a suede or leather boot. Suede would connote a more casual feel, while leather the opposite.

What won't be in doubt is if you opt for a Chelsea boot you will get those clean lines and slim silhouette which is always of complimentary benefit from formal attire.

As a style tip we would recommend a darker trouser to what is being worn on top. Not only does this lend itself better to alternating between a brown or black Chelsea boot, but allows for men to easily pick a more appropriate colour like white or blue for the top half.

How To Wear Chelsea Boots And Jeans

chelsea boots and jeans for men

No matter the colour, the humble jean dovetails nicely with a pair of Chelsea boots. There are multiple different ways to style dependent on the occasion and colours you want to pick.

What Colour Jeans

Taking our colours all the way to the darkest palette and wearing head to toe black is a refined pick that is great for evening or daywear. The jeans need to be slim fitting to accentuate the male figure and the Chelsea boot will keep the eye moving all the way down without breaking the look.

At the other end of the menswear scale, a light blue or even white denim teamed with brown Chelsea boots can help you screaming Italian flair. It's bold, but when done right can look fantastic in the summer.

Double Denim

In order to make this outfit as effective as it can be, play around with the colour. Not every denim jacket will work well with every jean. So, this might take some trial and error to get right. Look for black or dark grey on top and navy blue, even selvedge for the bottom half. We also like how adding a cuff to the jeans (provided the length is right) can add a nice touch of contrast sitting above the Chelsea boots.

Roll Neck Jumper and Jeans

Considering its versatile place within the wardrobe of men, its no surprise that the roll neck works so well with Chelsea boots. The roll neck does an admirable job of slimming the physique up top in a similar way to how good fitting jeans can do it on the bottom. Add to this a pair of Chelsea boots and you can't go wrong.

How To Wear Chelsea Boots And Leather Jacket

chelsea boots with leather jacket

As we previously mentioned, the Chelsea boots has us thinking of the 60s heyday of swinging London because its popularity was cemented at this time in style history. The post-era to this involved an explosion of rock and punk in the capital as London has always being a central point for the music world.

The leather biker jacket fabulously embraces the rebellious nature of this later musical period. Partnering it with a Chelsea boot screams London attitude and is a look you would expect to see on some of the most famous rock stars of that day.

Get additional rock star points by sticking a band t-shirt underneath. Though this can often look at bit forced. A simple colourway in black or white should be all this outfit needs. The jacket and boots are the main attraction, so keep the other elements of the outfit as unfussy, refined pieces.

If you were in doubt, it is always a black leather jacket and black Chelsea boots for us.

Final Note

It doesn’t matter what type of clothes you plan to wear, if you feel comfortable and confident in them then there is always a Chelsea boot to match. Chelsea boots work well throughout the different seasons, have a timeless aesthetic and will remain in trend for a long time to come. So, we recommend investing in a pair, paying close attention to and caring for, the quality of the leather and suede material. 

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