How To Wear Chelsea Boots 6 Different Ways

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. Enter stage right, how to wear Chelsea boots.

Learning how to wear Chelsea boots will be the most versatile stomper lesson you will get this season. They pair effortlessly with tailoring, work well with selvage denim for hardwearing, Western-inspired style or with some black skinnies for more of a grungy feel.

The first instruction in how to wear Chelsea boots is: 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 from a great boots brand 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.

6 Ways To Wear Chelsea Boots

Around Town

Nothing screams “errands” 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, who also know a thing or two about how to wear Chelsea boots (and not have it wear them). A good blazer will work a treat paired 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.

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Creative Metropolitan

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. This means you no longer have an excuse to not know how to wear Chelsea boots.

Brown is the color 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.

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Modern Rockstar

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, you will find somewhere there who knows how to wear Chelsea boots. 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.

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Sleek Company Man

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 learn how to wear Chelsea boots for a new spin and 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.

How to Wear Chelsea Boots

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Well-Heeled Weekender

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 a lesson in how to wear chelsea boots, 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.

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Workwear Nut

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. Thus, learning how to wear Chelsea boots 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 favorites like a plaid overshirt, ribbed knitwear, and a fisherman beanie will see you complete the style. Don’t go extravagant on the color palette either, workwear is about comfortably blending in and not trying to photobomb every catwalk candid.

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