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Unless you’ve got a walk-in-wardrobe the size of Narnia and a golden bounty as big as El Dorado’s, chances are you’re going to have to wear your newly purchased footwear more than once. Which also means you’re going to need a pair that goes with more than just those pleated pinstripe trousers you drunkenly bought while browsing the internet late at night.
Step forth then the Chelsea boot – the most versatile stomper in the menswear jungle. They pair effortlessly with tailoring, work well with selvedge denim for hardwearing, Western-inspired style or with some black skinnies for more of a grungy feel.
Black is the most versatile choice, able to go with any trouser colour or style. Brown works best with lighter and mid-wash denim, and a midnight blue pair can look especially strong alongside some slim black trousers.
A streamlined, slim and tapered Chelsea boot tends to be smarter and will look better worn with equally sharp tailoring as a result. A pair with a chunky rubber sole on the other hand is the way to go for hardier weekend looks.
Whichever style you go for you’ll get away with wearing them under some billowing wide legs, but you’ll be missing half the show if you do so – aim for a tapered hem to allow the boots to shine. Bigfoots among you should also watch out for pointed boots that can end up looking canoe-like, so head for more flattering rounded toe shapes instead.
Apart from these simple rules, the Chelsea boot is one of the easiest footwear styles to get right, working for occasions that stretch right across the dress code spectrum. Got a date? Casual work pints? A big interview? You only need one pair of boots for the job.
Nothing screams “cad” more than a pair of oh-so-dandy Chelsea kickers but if you’re going to complete the look you’re going to have to get with its friends. A natty blazer will work a treat pared down with a simple sweatshirt or tee underneath and some easy to match pleated trousers below.
If you’re keen to break out of that office mentality though, chuck the blazer and opt for a slick overcoat instead and pair with that other staple of gentleman rogues, the roll neck. Assuming you’ll be hopping from one bar to another, the chunkier the better with your knitwear.
You’re one of these young creative-industry types who works for a small architecture firm that almost definitely has an office dog. You’re actively encouraged to wear laid-back denim in the office and by hell you’re going to abuse that rule.
Brown is the colour of the day here. It’s far more casual than its black counterpart, especially if you have yours decked in some rough and ready suede. Lighter indigo shades of denim are particularly effective as they’re more casual than dark raw denim. Take it easy up top – a simple shirt or hoodie that tonally matches your boots will work an elegant treat. Remember the key is to look like you don’t care, when in all actuality you really, really do.
Fancy adopting the rockstar look but can’t pluck a six-string to save your life? Put that Fender away and make for the black section of the menswear department. The shade is synonymous with rockstar chic, as is the leather jacket. Pop them all together with a jazzy tucked-in shirt, some slim jeans and those trusty Chelsea boots for a play right out of the Alex Turner lookbook.
If you don’t have the rockstar bank account maybe swap the often-pricey leather jacket for a simple unstructured overcoat, but keep that patterned shirt. You want that ostentatious pop to make your ‘fit gleam.
The toning down of office dress codes hasn’t just meant the unfurling of those tie knots. Chuck the dress shoe away too, or at least give it a rest, and take the Chelseas out for a spin for a great way to stomp a bit of flair around the place without losing any of the smartness.
Slot them in underneath some office trousers, preferably cropped if you want to keep the silhouette sharp and prevent bunches at the hem. The boot height will also keep your ankles guarded – let’s not free the mankle when the temperatures are subzero. Wear a fine gauge knit up top with a simple work shirt, or a double-breasted blazer – one of the key trending pieces for the year ahead. Make sure everything is fitted around the office as anything oversized is best left on the catwalk or your Instagram feed for the time being.
If you’ve broken past adolescence you shouldn’t still be spending your weekends slobbering about the place in sweats. Level-up your weekend game by replacing those tatty old sneakers for some natty new Chelseas and bring some smartly cut denim to the party while you’re at it.
A relaxed, unstructured blazer is another classic smart casual play that works with dark denim as does one of this season’s on-trend outerwear pieces, the shearling jacket. Keep the shirts away for these two days and opt for some knitwear by itself instead – aim for warm neutrals like browns and blues, as black is just a little too serious for after 5pm on a Friday.
Workwear is very much in at the moment, an easily accessible trend that is giving the pretentious stylings of high fashion a real run for its money. The well-heeled Chelsea isn’t a natural bedfellow, but rounded versions that echo work boots slot in well. Also look for a Chelsea that has a chunkier tread to fit into the utilitarian ethos.
Elsewhere a rough and ready turn-up on your jeans will possess just the right amount of devil-may-care attitude, while workwear favourites like a plaid overshirt, ribbed knitwear, and a fisherman beanie will see you complete the style. Don’t go extravagant on the colour palette either, workwear is about comfortably blending in and not trying to photobomb every catwalk candid.