HOW TO WEAR CONVERSE HIGH TOPS – MEN’S MODERN STYLE GUIDE 2023
Sneaker releases are now so frequent that describing the flurry of brand new kicks as ‘arrival’ will no longer suffice, the phenomenon now has its own noun ‘drop’. We’re ready for some kicks (not kicks), but truth be told, we’re always drawn back to old favorites, and there are few styles we wear better than Converse high tops.
The brand’s Chuck Taylor All-Star Classic (to name the full name) has enjoyed continued success since the rubber-soled basketball shoe hit the ground running nearly 100 years ago, and that’s because the iconic design and unmistakable silhouette are one of them. of the most versatile styles ever.
“The appeal of a pair of Converse high tops lies in their ability to complete almost any outfit: the style goes beyond the gym script, the dressy/casual jacket and even the [classic] boy,” says Chris Gove, creative director of the British brand. Percival. “Retro and modern, Converse is a timeless choice in the minefield of trainer hype and is much more cost effective.”
There’s no denying that this iconic style of sneaker is universally loved, but with so many styling options, deciding how to wear Converse high tops can be a little tricky. Because we’re nice like that, we’ve listed the best ways to wear them below.
With Cropped CHINOS:
Chinos and Converse high tops have a lot in common: everyone has had them or thought about them at some point. If you’ve formed a strong mental association between chinos and middle-aged mediocrity, a pair of All-Stars is just the thing to deflect accusations of tepid dressing.
But regular chinos in a similar style to what your dad might wear won’t do here: you’ll need to get a little more menswear than a pair that’s cropped at the hem. The tight shape of high tops also doesn’t mess with acres of fabric, so stick to fitted styles to maintain a sense of balance. Also avoid any other pockets as they will disrupt the clean lines you are aiming for here.
Since chinos sit somewhere in the middle of the smart-casual continuum, the Brittany top is a solid finishing move for the fence. Plus, when this French classic is teamed with sporty Converse, there’s less risk of becoming some fashion cliché on the Riviera.
WITH SHORTS:
At first reading, high-top sneakers and shorts worn together sounds like territory no grown man should travel into. That combination inexplicably works, and it works damn well. In fact, swapping your worn-out sneakers for new Converse high tops is a good way to stand out when everyone else is playing it safe in the sun.
Follow the rule of opposites when you wear these northern sneaker sneakers with shorts: if your shorts are dark, choose light Converse and vice versa. Then, to dispel any lingering suspicions that you’re in the school holidays, wear a bold striped t-shirt rather than a plain t-shirt.
Since shorts are already so formal, regardless of whether you choose light or dark thigh-high tops, you need to make sure that your kicks are always clean: cleanliness is next to godliness and all that.
WITH RAW SELVEDGE JEANS:
They’re hardly a pair of work boots, but Chucks have a sense of everyday utility because you can wear them with just about anything. The same utility makes it particularly well-suited to raw-hem jeans, the holy grail of denim when it comes to diehards.
When these durable leg warmers are worn with Converse high tops, it’s hard to see why so many men are still devoted to their tight black skinnies and minimal white trainers. Raw denim offers a masculine, carefree look that perfectly matches the slim profile of a canvas classic.
Unlike a heavier shoe that will veer too close to Saturday night with the boys territory, a pair of white Converse will alleviate any turn-of-the-millennium flavor voids. A simple sweatshirt on top keeps this collection of basics durable.
WITH A TAILOR:
It’s hard to imagine that just ten years ago, trainers paired with tailoring were considered sacrilegious sacrilege. Now, we’re pretty sure that over 90 percent of the male population has already tried some sort of low trainer with their tailoring. So Converse high tops offer a less well-trodden look with a suit and sneaks (and you don’t have to look like Doctor Who).
A navy, charcoal, black or green suit will work with white or cream high tops, but in summer a stone, beige or gray suit will look best with a dark pair. Try tonally matching what’s on your torso with your feet to pull the look together.
And if you’re not headed to Comic-Con, avoid the TARDIS thing by going casual with what you’re wearing under your jacket. A T-shirt, light knitwear or a T-shirt with a collar are the safest styling options.
WITH WHITE DENIM:
White jeans are about as edgy as menswear gets. Slim down and pair them with tassel loafers and you’ll channel European playboy without the yacht. Throw in some high-top Converse and relax with your cut, and suddenly you’re one of those casual menswear types who’s made a career out of Instagram.
While both dark and light high Converse will work well with white jeans, the look works best in monochrome. So use all white for the bottom half of the look and layer darker shades on the top half. Alternatively, if distressed shades aren’t really your vibe, a short-sleeve printed shirt will work well here, and your classy choice of footwear will make you less likely to be mistaken for a BBQ tong-in-boss.
WITH LIGHT WASH JEANS:
This look was inducted into the menswear hall of fame thanks to Marty McFly’s epic skateboard turn in Back To The Future. Decades later, the light jeans and Converse high top combo still works as well as ever, even if this vest and plaid shirt haven’t aged so well.
Wear a white t-shirt tucked into jeans for an eighties vibe, but try layering a loose work jacket to keep the look current. Also, fit is crucial here: anything that might cut off your circulation is not recommended.
WITH SPORTSWEAR:
There’s no doubt we’re in the realm of high-end sportswear, which means trainers and tracksuits have ditched suits and smart shoes as the de facto men’s uniform. But while bold sneakers and joggers can look good in a street style shot, unless you’re an incredibly bushy kid in sportswear, high tops are a safer bet.
By introducing a few All Stars into the mix, you’ll keep the outfit relaxed but won’t risk looking like modern sports spice. For a nod to the latest menswear obsession, choose side-stripe trousers to pair with your Converse and do it like Goldilocks: aim your hems towards the center to ensure they’re neither cuffed nor baggy.
To avoid the crazy vibes of the whole ensemble, throw on a denim jacket and a simple white t-shirt.

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