How To Wear Chelsea Boots With A Suit: 18 Stylish Outfits For 2024

In the annals of men’s footwear, few items have demonstrated such timeless appeal as the Chelsea boot. We mostly associate their genesis with the 60s (the name was derived from their popularity on the Kings Road in Chelsea, London) but Chelsea boots actually originate in the Victorian era, where the earliest incarnations started life as riding boots that could be put on and taken off with ease thanks to the elasticated ankle insert.

Although menswear has massively lurched towards a streetwear-dominated aesthetic in the last decade, the Chelsea boot remains a steadfast addition to the modern footwear rotation, able to seamlessly traverse both smart and casual looks with aplomb.

While Chelsea boots have spent much of their modern history at the end of tapered jeans, the modern breed of boot has become much more adept at pairing with tailoring, and so we’ll show you exactly how to get these two dance partners to waltz into your wardrobe.

When to wear Chelsea boots with a suit

Canali

Where once the suit was simply a garment one would wear to the office, today it has become much more of a fashion item, thanks to a modern relaxed silhouette and the once hegemonic domination of the shirt and tie giving way to the likes of polo shirts, T-shirts, crew-neck sweaters and turtlenecks.

Boots and suits now harmonise beautifully in both smart and smart-casual settings. For the majority of people, the office is the place they’re most likely to find themselves wearing a suit, and it’s an environment ripe for the Chelsea boot.

With dress codes now more relaxed, the Chelsea boot really comes into play, with polished black black leather styles delivering confidence and individuality to a navy or charcoal suit. For special occasions, a pair of suede Chelsea boots can combine with a well-tailored tuxedo to create an eveningwear ensemble with a garnish of attitude and modernity.

The best suits to wear with Chelsea boots

Hackett

Chelsea boots are versatile enough to complement a range of suits but the fail-safe option is the modern, well-fitted single-breasted style with a single button closure. Unstructured blazers also better emphasize the relaxed elegance of Chelsea boots than something fully canvassed and rigid.

The jacket is actually of less importance than the trousers, though, which should feature a natural taper from the thigh to the ankle. Contemporary, relaxed-fit suiting featuring baggy, wide-leg pants will not work since the hem of the trousers will hide much of your boot. And when that happens the boot’s tapered toe will make it seem like you’re wearing winkle pickers (never a good look).

As for fabric, suits cut from textural cloths will complement suede Chelsea boots best, while classic high0twist merino wool suits in navy and charcoal are perfect with smarter black leather versions.

The best Chelsea boots to wear with suits

Velasca

When selecting a pair of Chelsea boots to wear with your suit, consider suede for a more casual appeal and leather for a formal touch. Black leather Chelsea boots exude sophistication and are an ideal choice for business settings and eveningwear, while brown leather or suede boots are versatile for more relaxed tailoring, or tonal colours.

Pay attention to details such as the toe shape: Chelsea boots typically come with a tapered toe rather than a pointed finish, but they can vary greatly. Rounder shapes are the more versatile, but a sharply chiselled or squared-off boot can look supremely elegant.

18 modern Chelsea boots with a suit outfits

Navy double-breasted suit with black leather Chelsea boots

Dunhill

Elegant, sophisticated, and impossible to get wrong, pairing a dark navy suit with polished black Chelsea boots is a recipe for sartorial success.

This double-breasted style has had the formality dialled down a notch with the turtleneck, which perfectly suits the Chelsea boots’ laid-back attitude.

Navy suit with tan suede Chelsea boots

Officine Générale

This is quite an adventurous fit but what makes it work is the rebellious inclusion of the denim shirt to completely dress down the navy suit.

The tan suede Chelsea boots just reinforce the subversion. It helps that the suit has a soft textural handle too.

Camel suit with brown leather Chelsea boots

Sandro

We love the tonality of this look, elevated by the subtle check of the camel suit and perfectly bookended with a pair of smart chocolate brown Chelsea boots.

It’s smart yet cool, with the slim silhouette giving it a very Parisian attitude.

Grey check suit with black leather Chelsea boots

Boglioli

Opting for just two colours in your look keeps things simple and effortlessly chic. The addition of the Prince of Wales check ensures the suit has depth, while the black boots and black knitted polo shirt tie it all together with aplomb.

Camel double-breasted suit with brown suede Chelsea boots

Boglioli

Tonal dressing is so easy to pull off, and the results are always excellent so we’re not sure why more men don’t do it.

This look of rich cream and tan tones is perfectly balanced by the stronger chocolate brown suede of the Chelsea boots, while the belt detail and the peep of white T-shirt complete the look.

Black double-breasted suit with black leather Chelsea boots

Mango

If only all Casual Fridays looked like this. An elegant black double-breasted flannel suit given the sprezzatura treatment thanks to the beige crew neck, while the black leather Chelsea boots complement the look with a minimalist attitude.

Blue suit with black leather Chelsea boots

There was an old adage that went something like, ‘only wear black and blue if you want to look like a bruise’, but thankfully it doesn’t stand true, as evidenced here.

Cut with a slim modern silhouette, the suit trousers are perfectly proportioned, while the addition of the grey crew neck helps make the Chelsea boots feel cohesive.

Brown double-breasted suit with brown suede Chelsea boots

Boglioli

While this look works perfectly on the colour palette alone, it’s really all about the texture of the suit and how it riffs off the texture of the suede brown Chelsea boots.

Masterful.

Grey-blue suit with black leather Chelsea boots

Digel

If there was ever an image that showed you how critical the taper of the suit trouser is in order to perfectly accommodate a pair of Chelsea boots, it’s this one.

Note how the trousers just seamlessly integrate with the boots to create one long, slender and masculine silhouette.

Grey/black check suit with black leather Chelsea boots

Digel

Although this model has been cleverly styled so that the black shirt and tie complement the black tone of the Chelsea boots, the more important factor is the black check of the suit.

It’s always a good idea to match a colour from whatever type of check you’re wearing in one or more of your shoes and accessories, to tie everything together.

Grey flannel suit with charcoal suede Chelsea boots

Marks & Spencer

The grey flannel suit is one of those timeless garments that every man should own.

Were it not for the soft nap of the flannel, then a pair of black leather Chelsea boots would be a great option. However, the addition of suede seems to bring out the texture of the tailoring.

Light grey double-breasted suit with black leather Chelsea boots

Moss

It’s not always easy to wear strong contrasting colours especially when suiting is involved, but when the tailoring is this light, trying to play a tonal game with the boots will not work. Instead you need to create a sharp striking finish with a pair of black leather Chelsea boots. If your suit’s buttons aren’t black or dark, then use a black belt to bring the look together.

Off-white suit with black leather Chelsea boots

MOSS

Much like the previous look, this works because of the strong contrast created between the black leather boots and the off-white suit.

The addition of the black turtleneck adds to the effect much more than if a shirt and tie was being worn.

Textural charcoal suit with black leather Chelsea boots

Reiss

This is an excellent business-casual combination, using the flecks of black in the textural charcoal suit to complement the black leather Chelsea boots.

The olive green tee keeps the ensemble relaxed without softening the sharpness of the tailoring.

Navy windowpane check suit with brown suede Chelsea boots

Ralph Lauren

A beautiful blue flannel suit with a grey windowpane check is never a bad idea, and this one has been styled well by using a grey turtleneck to complement the colour of the check.

The brown suede Chelsea boots offer a counterpoint to the colours in the suit, as well as complementing the soft nap of the flannel.

Blue suit with black leather Chelsea boots

Tiger of Sweden

This suit’s superpower is its svelte silhouette, which is perfect for tall, slim figures.

The rich tone of the blue is playful but also businesslike, so brown suede Chelsea boots would soften the sharpness. Instead, opting for black leather boots adds to the suit’s angles and attitude.

Black suit with black leather Chelsea boots

Tiger of Sweden

For a smart evening event, going with a monochrome look such as this one is a fail-safe, since the interplay between the sharp black suit and crisp white shirt is instantly captivating.

Opting for black leather Chlesea boots and a black tie are the cherries on the sartorial cake.

Light grey suit with grey suede Chelsea boots

Windsor

The vast majority of Chelsea boots are either black or brown, but you can certainly find other tones if you look hard enough.

This grey suede pair has a nice dusty texture to them, which adds a load of dimension to a grey suit that could otherwise fall quite flat.