How to Wear Chelsea Boots: The Best Ways to Wear Chelsea Boots

how to wear chelsea boots

Over the past couple of years, you may have noticed an increasing number of boots dotting the shelves of stores and the sidewalks of urban centers. Among them, there is a high chance you have seen or even worn one such kind called Chelsea boots – a design named after the district of Chelsea in the United Kingdom.

This type of boots has become highly popular with men who seem to prefer a clean-lined, lightweight, and versatile design over the generic boot with shoelaces. If you are one of these men or are simply curious to find out how to wear Chelsea boots, read on.

Back in 1851, Mr, J. Sparkes-Hall, the official cobbler of Queen Victoria, developed a boot that had side elastics instead of shoelaces. Pleased, the queen would style her brown Chelsea boots when going for a walk or horseback riding. Little did she know then that the trend would stick.

But it wasn’t until the Rock n’ Roll wave of the 60s –  when artists such as the Beatles and Rolling Stones began to wear Chelsea boots outfits – that this kind of shoes popularized among non-monarchs. After vanishing from wardrobes and shoe shops for a few decades, the men’s Chelsea boots have returned with full speed in 2017, with style icons such as David Beckham and Harry Styles adhering to the trend.

The reason behind the popularity? Similar to Boat shoes, Chelsea boots are practical, comfortable, and look great with nearly any attire. Find out more about how to style Chelsea boots on the guide below.

Chelsea Boots Styles

chelsea boots styles

Being such a versatile type of shoes, it is not difficult to figure out the best style of Chelsea boots to wear. But since there is no such thing as too many ideas, we thought we’d break down some of the style variations that can be found out there and on which occasions they work best.


The suede Chelsea boots are probably the most casual type available – both for the aesthetics and durability of the material. This kind of Chelsea boot goes well with jeans, colorful twill pants or chinos. Wear suede Chelsea boots in any casual occasion by combining it with shirts, knitwear, regular t-shirts, or even flannel. Beyond casual looks, this variation can match outfits of more liberal work environments just by adding a dress shirt and a blazer.


Pair your rustic Chelsea boots with jeans of any kind – from classic to destroyed models. This style of men’s Chelsea boot also fits perfectly into a “lumberjack look” with a red and black plaid shirt. It can be even more casual than Chelsea in suede, so it needs a bit more attention when considered as a work outfit.


In the case of brogue Chelsea boots, the type of leather will be the primary element: if it is a more polished leather it should be worn with more formal clothes in a combination of tailors pants and a dress shirt; if the leather is rougher and more opaque, try to combine it with jeans or chinos and a casual shirt or t-shirt.

Dress Boot

The dress Chelsea boot can be easily thought of as a pair of dress shoes since its polished leather renders a very clean and elegant look. It is common to see this style of men’s Chelsea boots in the fall or winter when guys wear a thick stocking underneath the dress pants without making it visible. However elegant it may be, dress boots are still not suitable for weddings, when a pair of dress shoes with shoelaces are still the preference. Choose this type of footwear when looking for a Chelsea boots outfit that prioritizes elegance and comfort.

Full-grain Leather

The kind of men’s Chelsea boots made of full-grain leather sits between the suede and the aforementioned dress style in terms of casualness. Hence, this model works more like a blend of smart-casual or business-casual, giving space to a tinge of informality in more formal looks.

How to wear Chelsea boots

Now that you are familiar with the main types of Chelsea boots, let’s have a look at how to combine them with different pieces of clothing according to a particular occasion.

With Skinny or Slim-fit Jeans

A feature that distinguishes the design of Chelsea boots from that of most other boot styles is that it has a very narrow shaft and a straight upper part, making it an ideal choice of footwear to combine with tighter jeans such as skinny or slim fit. Ideally, if the jeans fit just right can wear them without having to slide the bottom hem inside the shoe. Alternatively, what many people do when the jeans are a tad too long is fold the hem until it stays just above the boot’s shaft, giving an extra touch to the look.

With a Basic Look

One of the upsides of Chelsea boots is the fact it can be worn discreetly, without embellishing the look. That means you can mix and match it with all sorts of basic clothing without attracting much attention and keeping a casual style.

With a Suit

While the more casual Chelsea boot styles go well with basic clothes, the more sophisticated ones match perfectly with tailor-made costumes, creating an elegant and charming complement. Moreover, the relaxed character of Chelsea boots can strengthen formal outfits whose look leans towards casual by choosing knitwear and blouses instead of the usual shirt and tie combo.

With Heavy Coats

When thinking of looks that feature heavy jackets – such as pea coats or chesterfields – we automatically think of heavier duty boots as a means to counterbalance the composition. But due to its more plain design, Chelsea boots also go well with winter wardrobes, refining what could otherwise be an overly rough look.

With Rocker-style Garments

If you are an advocate of leather jackets, rock band jerseys, and skinny dark jeans, do consider getting yourself a pair of Chelsea boots. Because this type of boots is often of more opaque color and straightforward designs, they are less likely to contrast with the rest of the composition. Pick a simple black full-grain or a very neutral gray-lead suede to stay on the safe side. Should you want to break the norm a bit, consider a pair light brown Chelsea boots.

Indulge in The Colors

When wondering how to wear Chelsea boots, not only can you fiddle with different styles and designs but should also make the most of the many colors available.

Although the more traditional tones – such as brown, black and navy blue – are the easiest ones to find and safest to wear, there are an array of hues – going from beige to orange, light gray, cobalt blue, etc. – to match your personal preference without steering away from the essence of a Chelsea boot. Finally, pay attention to the elastic on the side of your Chelsea boots for it can also assist on the look through color contrasts.