High-top sneakers, once the footwear of choice for athletes have come a long way since their invention in the 1890s. Beloved by everyone from jocks to counter-culture anarchists, the high-top is the epitome of classic cool. Whether you’re a black-clad Indie rocker or you’ve got a pair of Chuck Taylors as your go-to weekend shoe – this sneaker is renowned for its versatility.
It’s also thanks to their iconic status that the high-top can be worn with virtually any ensemble. Here, we’re breaking down the best way to style them, regardless of what the occasion might be.
In This High Top Story…
Know Your High Tops
Whether you’re shopping in the luxury aisle or the streetwear lane, make sure you pick the right pair of shoes for the right outfit. Generally speaking, clean looking high tops work better with workwear, suits and smarter attire.
How To Wear High-Tops With Jeans
High-tops with jeans are perhaps one of the most classic casual ensembles in the book. Cool without being pretentious, it’s a foolproof option for coffee or a weekend wander. Choose a classic high-top style like a black or white Chuck Taylor and pair them with similarly timeless denim. In this case, you can’t go past a pair of blue-wash Levi 501s. Top it all off with a plain, crew-neck tee shirt in white or black.
If you’re after something slightly more inventive than a plain tee, jeans with a denim shirt make for a classic pairing – particularly when offset by white or boldly coloured high-tops. Think about wearing contrasting jeans and a shirt (black and indigo) and styling them with contrasting shoes.
Given the oftentimes slim design of high-top sneakers, it’s best to offset them with slightly looser-fitting denim. Opt for slim or boot-cut styles that ensure your outfit doesn’t appear top-heavy and style by cuffing at the ankle. Overly skinny jeans evoke a bygone era of early 00s boy bands – don’t go there.
Nudie Grim Tim Indigo Myth
An icon in denim. They work perfectly with high tops. Slim fit stretch jeans with a straight leg in a dark blue wash with authentic wear-marks. Made from organic cotton.
How To Wear High-Tops With Chinos
Chinos are often lumped in as part of the smart casual dress code, but they hold their own as streetwear too. When paired with high tops, it makes for a cool, slightly norm-core look and ups the ante on your standard jeans and tee combo.
In terms of styling, aim for the smarter end of urban, opting for beige or navy chinos paired with a polo shirt or a striped Oxford. Leave the shirt untucked and cuff the chinos to show off your high-tops. This is the perfect outfit for brunch or indeed any other low-key weekend activities.
When it comes to fit, the same rules that apply for jeans apply here. Think about opting for a slim or classic fit versus a super-skinny style. It will look better and also help you convey that classic-yet-street aesthetic.
Bonobos Stretch Washed Chino 2.0
Updated with non-iron, 4-way stretch cotton & a secure zip pocket.
How To Wear High-Tops With Shorts
You’d be forgiven for thinking I’m mad for even mentioning high-tops and shorts in the same sentence. And, while not the easiest look to execute, when styled well this combination can look sensational.
The key thing is to play with proportion. Because high tops generally fit close to the foot, they look best when contrasted with baggy shorts and voluminous shirts and tees. Harking back to a 90s skater aesthetic, this kind of ensemble can be freshened up by choosing neutral colours and high-quality fabrics.
Look at stockists such as Venroy and Bassike for versatile, easy-to-pair options that will work seamlessly with classic high-tops from the likes of Converse and Springcourt.
G-Star Sport Trainer Shorts
This pair of Sport Trainer shorts is cut in a straight fit and shows a flap pocket at the front leg. Inset pockets are combined with single welt back pockets.
How To Wear High-Tops Formally
Despite common belief, high-tops are not only for casual ensembles. Since the early 00s, designers have been producing high-end options that work just as well with a pair of jeans as they do with the tuxedo. The trick lies in finding the right pair for your occasion.
For very formal events (i.e. black tie), a high-top sneaker can be the perfect way to experiment with high-low dressing. Go for a well-tailored tuxedo and cropped trousers (there’s nothing worse than trousers bunching around your ankles because they’re caught on the lip of your shoes). Pair this with premium high-tops in darker shades from the likes of Christian Louboutin or Giuseppe Zanotti. Play with textures and finishing details like studs or even sparkles for some added panache.
For more relaxed occasions (think cocktail parties), you can afford to go even bolder with your high-top style. Pairing black jeans with a blazer and tee-shirt looks great with a pair of statement, patterned high-tops from somewhere like Dior Homme.
How To Wear High-Tops With Activewear
It’s easy to forget that high-tops were originally designed as basketball shoes. Today, they make for the perfect accompaniment for a more contemporary take on sportswear – particularly when worn as part of an athleisure ensemble.
Ideal for relaxed weekend strolls (but certainly not for any heavy-duty exercise), high-tops look sensational paired with a slim pair of tracksuit pants, black tee, and quilted gilet. Opt for either a chunky retro pair of kicks (think Nike Airforce Ones) or a more classic canvas style to complete the look.
High tops and work out shorts also make for a strong, if slightly bolder look. Keep your ensemble monochrome, matching the shorts with a grey tee and a pair of black canvas high-tops for maximum impact.
Gymshark Rest Day Essential Shorts
Meet your key rest day pieces in the Rest Day collection, with styles as easy to wear as your day is easygoing.
High Tops With Cargo Pants
Hear me out.
Now, there are two types of cargo pants; cuffed and non-cuffed. For the cuffed – those that look like joggers, pairing them with high tops is almost the same as pairing activewear with high tops, and we just discussed that.
The non-cuffed cargo pants, on the other hand, are usually baggy and they are very much the trend right now. You’ve probably heard that high tops and baggy pants do not go together, but I have a different opinion.
This doesn’t always automatically work, and most times it comes down to how the pants sit on your high tops for the longer baggy cargo pants. If your cargo pants are a bit short, that’s perfect to pair with high tops. But if they are long, you shouldn’t wear them with thin high tops like a Converse. Go for a chunkier pair like the Nike Dunk Highs, Jordan 1 Highs, or even Air Force 1 Highs. A non-Nike alternative is the Forum Highs
It might be a bit tricky to make this work, but it’s going to look really good.
G-Star Raw Rovic Zip 3D Regular Tapered Pants
The Rovic Zip 3D Tapered is constructed from finely woven twill with a soft hand-feel.
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