The flurry of brand new kicks is now so common that describing it as ‘arrivals’ is no longer adequate; the phenomenon now has its own noun, the ‘drop.’ We’re all for multiple kick drops (not drop kicks), but the truth is that we’re always drawn back to old favorites, and there are few styles we’ve worn more than Converse high tops. Since the rubber-soled basketball shoe hit the ground almost 100 years ago, the brand’s Chuck Taylor All-Star Classic (to give it its full name) has had an unbroken run of success, and that’s because the iconic design and unmistakable silhouette make for one of the most versatile styles of all time.
The appeal of a pair of Converse high tops is their ability to go with almost any outfit: the gym rat, the smart/casual blazer guy, and even the classic lad can all wear them. Converse, which are both retro and modern, are a timeless choice in a sea of hype trainers and are far more cost effective. This iconic sneaker style is undeniably popular, but with so many styling options, deciding how to wear Converse high tops is a little more difficult. Here are the best ways to wear them below.
Paired With Cropped Chinos
Chinos and Converse high tops have a lot in common: everyone has tried them on or thought about trying them on. If you’ve formed a strong mental association between chinos and middle-aged mediocrity, a pair of All-Stars is just what you need to avoid accusations of tepid dressing. Standard issue chinos of the type your father might wear won’t do here: you’ll need to get a little more menswear with a pair that are cropped at the hem. The narrow shape of high tops also doesn’t play well with a lot of fabric, so opt for fitted styles to maintain a sense of balance.
Additional pockets should be avoided as well, as they will disrupt the clean lines you’re aiming for. Because chinos are somewhere in the middle of the smart-casual spectrum, a Breton top is a solid fence-sitting finishing move. Plus, when you pair this French classic with sporty Converse, you’re less likely to become a walking Riviera chic cliche.
On the surface, high top sneakers and shorts worn together appear to be uncharted territory for a fully grown man. Inexplicably, the combination works, and it works exceptionally well. In fact, swapping out a pair of worn-out plimsolls for a pair of brand-new Converse high tops is a great way to stand out in the sun when everyone else is staying safe. When pairing these northward-creeping sneakers with shorts, follow the rule of opposites: if your shorts are dark, pair them with light Converse, and vice versa.
Then, to dispel any lingering doubts that you’re on vacation, wear a bold stripe shirt up top rather than a plain tee. Because shorts are already informal, whether you wear light or dark high tops with your thigh grazers, you’ll need to keep your kicks clean at all times: cleanliness is next to godliness and all that.
Jeans With Raw Selvedge
Chucks aren’t exactly work boots, but they have a sense of everyday utility to them because you can wear them with almost anything. That same utility makes them a great match for raw selvedge jeans, which are considered the holy grail of denim by die-hard fans. When paired with Converse high tops, it’s difficult to understand why so many men are still stuck in their skin-tight black skinnies and minimal white sneakers.
Raw denim has a clean, masculine appearance that complements the slimline profile of the canvas classics. A pair of white Converse will temper any turn-of-the-millennium taste void vibes, unlike heavier footwear that will veer too close to Saturday-night-with-the-lads territory. On top, a simple sweatshirt will keep this collection of basics from looking sloppy.
Scotch & Soda
It’s hard to believe that just a decade ago, wearing trainers with tailoring was considered a sartorial sin. We’re pretty sure that by now, more than 90% of the male population has experimented with some sort of low top trainer with their tailoring. Converse high tops provide a fresh take on the suit and sneakers look. A navy, charcoal, black, or green suit will look great with white or cream high tops, but a stone, beige, or grey suit will look best with a dark pair in the summer.
To properly tie the look together, try tonally matching what’s on your torso to what’s on your feet. And, unless you’re going to Comic-Con, avoid doing the TARDIS thing by dressing casually underneath your suit jacket. The most secure styling options are a T-shirt, a lightweight knit, or a grandad collar shirt.
The Idle Man
Combined With White Denim
White jeans are about as unruly as menswear gets. If you wear them skinny and pair them with tasselled loafers, you’ll look like a European playboy without the yacht. Introduce some high-top Converse and a relaxed haircut, and you’ll be one of those Instagram-famous menswear types. While both dark and light high top Converse will look great with white jeans, the look is best when done in monochrome. So, for the bottom half of your look, go all white, and then layer darker shades on top. If pared-back shades aren’t your thing, a printed short sleeve shirt will work well here, and thanks to your refined footwear, you’ll be less likely to be mistaken for the BBQ tong-wielder-in-chief.
With Light Wash Jeans
Because of Marty McFly’s epic skateboard turn in Back To The Future, this look was inducted into the menswear hall of fame. The combination of light wash jeans and Converse high tops works as well as it ever has, though the gilet and checked shirt haven’t aged as well. Wear a white tee tucked into your jeans to channel the eighties, but layer it with a loose worker jacket to update the look. Fit is also important here: anything that could cut off your circulation is not recommended. A relaxed leg shape with slightly cropped hems is preferable.
There’s no denying that we’ve reached peak sportswear, which means that trainers and tracksuits have surpassed suits and smart shoes as the de facto menswear uniform. While bold sneakers and joggers may look good in a street style shot, high tops are a safer bet if you’re not an impossibly swaggy sportswear kid. Adding some All Stars to the mix will keep the outfit relaxed without making you look like a modern-day Sporty Spice. To nod to menswear’s latest sportswear obsession, pair your Converse with side stripe trousers and, like Goldilocks, aim for the midpoint with your hems, ensuring that they’re neither cuffed nor baggy. Wear a denim jacket and a simple white T-shirt to avoid the full-kit wanker vibes.