How To Wear Chelsea Boots: 6 Modern & Stylish Outfits For Men

The Chelsea boot is a true design classic. Over the years, it has become something akin to uniform for some of history’s most discerning subcultures. This modern classic stormed festival stages at the peak of rock music’s golden era; it strode around south west London in the 1950s on the feet of the city’s coolest young musicians and artists; it graced the deck of many a Vespa in the 1960s and 1970s; and has spent every year since cementing its place as a men’s fashion icon.

To say the Chelsea boot is ingrained in the very fabric of menswear is an understatement. Yet in spite of its rampant popularity and shoe-rack-staple status, it’s something that a considerable amount of men still have trouble styling correctly.

Sartorial confusion isn’t uncommon when footwear ventures north of the ankle. Yet styling Chelsea boots is actually pretty simple. The trick is to know what works and stick to it. With that in mind, we’ve broken down six key ways to wear this footwear hero so that you can nail it every time.

Suited (And Booted)

Everyone’s heard the phrase “suited and booted”, but it’s not really supposed to be taken at face value. Suits and boots rarely mix in modern menswear, and for good reason: a pair of big bulky winter boots with dress pants is never going to be a well-balanced look. However, there are a couple of exceptions to the rule and Chelsea boots happen to be one of them.

The low-profile shape and sleek silhouette mean that Chelseas are a viable option when it comes to teaming up footwear and tailoring. What’s more, they offer something a little different to standard Oxford or Derby shoes and can bring a touch of personality to an otherwise traditionally stuffy outfit.

Stick to slim-cut suits for the sake of balance. A Chelsea boot is a slim-fitting piece of footwear and overly wide leg openings or broad shoulders can throw your proportions off. The other thing to consider is colour. Black leather is a timeless choice that goes with everything from classic navy and grey tailoring to camel or beige summer suits.

Business Casual

Yes, it’s called dress-down Friday. No, that doesn’t give you carte blanche to rock up to the office in board shorts, flip flops and your old high-school leavers hoodie. What it actually means is to make your usual work outfit a little more laid back, and substituting your Derbies for a pair of Chelsea boots is an excellent way to get the ball rolling.

Admittedly, Chelsea boots may look a little out of place worn with your standard 9-5 wardrobe. Particularly if your office is on the stuffier, corporate side of things. The key to nailing business casual lies in switching out formal-leaning garments and making a few casual tweaks.

From the top down, think about layers. Instead of a simple shirt and suit jacket, why not incorporate some knitwear – a roll neck is a sophisticated piece that works on its own, or you can combine an Oxford shirt with a crew-neck sweater for a foolproof combination that still feels professional.

As far as legwear goes, don’t worry about it matching your jacket. Separates are a good way to tone things down without looking sloppy and the contrast created brings depth to the overall look. Again, make sure the pants are cut slim to match the shape of the boots and top it off with an overcoat or parka on colder days.

Smart Casual

One of the great things about Chelsea boots is how versatile they can be. Still, there’s one area of menswear in which they really excel themselves: smart casual.

Not too dressy, not too relaxed, the Chelsea boot sits directly on the line that divides the two, making it a solid option for things like dates, dinner out or evening drinks. They look the part with everything from jeans to dress pants and have a way of instantly lending even the simplest of outfits an air of refinement.

Working from the ground up, the first thing needed is a pair of high-quality Chelsea boots in dark leather. Suede will work too, but it does lean a little further towards the casual end of the spectrum. Next, jeans: a slim cut is essential, as is sticking to either very dark shades of denim or very light – stonewash and mid-wash have no place here. Last but not least, layers. Think fine-gauge knitwear, an unstructured blazer or light jacket and accessorise accordingly.

Night Out

As dress codes continue to relax, the days of nightclubs and bars operating no-trainers policies are long behind us. Still, if you do feel like giving your Common Projects a night off, a pair of Chelsea boots is the perfect alternative.

Sure, Chelsea boots are sleek, smart and streamlined, but they’re also bona fide rock ‘n’ roll icons. Use that thought as inspiration when styling them for a big night out and deploy other edgy staples to bolster their rebellious streak.

All black is a good way to go. If that’s a little too gothic for you, add a tonal element with some different shades of grey, or even a pop of white. In terms of garments, think leather and denim jackets, slim jeans, and don’t be scared to go for a printed shirt if it’s in need of spicing up.

Weekend

All too often, men take “casual” as a synonym for “boring”. When the weekend arrives, the same battered old pair of Converse are summoned from the shoe rack, the trusty jeans go on, along with a plain T-shirt, and that’s pretty much how it stays until bedtime on Sunday night.

When you spend a week dressing for work, it’s all too easy to become stuck in a style rut come the weekend. Here’s how you can use a pair of Chelsea boots to get your sartorial mojo back in time for Saturday.

Starting with the footwear, leather or suede boots are both good options. Stick with dark colours for leather, but feel free to venture into lighter territory where suede is concerned. Slim- and straight-fit legwear is always a winner at the weekend, whether jeans or chinos. If it’s denim, stick to casual washes like stonewash, mid-wash and grey. On top, keep things simple with layered basics like a well-fitting T-shirt, a cosy mid layer and a casual jacket (a bomber, overshirt or chore coat would work well).

Blue Collar

When thinking of workwear and Americana, it’s normally work boots and cowboy boots that spring to mind in terms of footwear. These are big, bold styles, so where exactly does the comparatively dainty Chelsea boot fit in amongst it all?

Well, Chelsea boots have evolved into different strains over the years. The ones with chunky commando soles and tough, rugged leather uppers are perfect for part of a western or workwear-inspired outfit.

You know the drill. Flannel shirts, trucker jackets, mid-wash denim, twill chore coats and the like. Keep cuts somewhere between relaxed and slim and the colour palette muted, except in the case of plaid shirts.