The Dos and Don'ts of Wearing Sneakers

Because sneakers aren't an excuse to get sloppy.
IMAGE Stores Specialists Inc.

If you’re one of those men rejoicing at the return of chunky athletic sneakers and tennis shoes, then you’ve got streetwear to thank. The meteoric rise of streetwear labels, not to mention the incarnation of Kanye West as a style force to be reckoned thanks to his Yeezys, has catapulted the hypebeast aesthetic, sneakers included, to glory.

While the recent sneaker culture allows you to get away with more style choices than ever before, that doesn’t mean showing up to a traditional wedding in your Air Jordans. Sneakers aren’t an excuse to get sloppy. If anything, they're an exercise in pushing rigid menswear boundaries, while still remaining sharp and on-trend. 

Here, a low-down on how to get away with wearing sneakers while still looking stylish.

Start with the classics.

If you’re getting started with sneakers, then skip the long lines for the newest hyped release and stick to classics. Get a pair of Adidas Stan Smiths, Air Force 1s, or the original Converse Chuck Taylor All-Stars for your beginner’s haul. Many new releases are an offshoot of a classic predecessor, the core of any sneakerhead’s collection.


The white sneaker is your best bet for a versatile shoe.

If you must insist on wearing sneakers with most of your wardrobe, then the white sneaker is your best bet. If your work or lifestyle allows you to wear smarter casual clothing, then get a pair of white dressy tennis shoes in leather. Pair with a button-down shirt and chinos or even a light, unlined daytime suit. You can also get a pair of white, low-top canvas sneakers. This will pair well with most casual clothing, chinos and denim included.

If you must wear chunky kicks, make them the statement piece.

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Chunky sneakers are hardly timeless footwear, but we’re not one to knock trends. If you find yourself drawn to loud, chunky sneakers, make them the statement piece of your outfit. Draw attention to your shoes' unique and vibrant design by leaving the rest of your outfit muted—think khaki joggers and a plain tee in neutral colors like black, white, or gray. 

Refrain from pairing straight-cut jeans with high-cut sneakers or dad shoes.

You’ve got several options when it comes to wearing high-cut sneaks or dad shoes: Pair them with joggers, rolled-up chinos, or anything that shows off the ankles. For a more urban aesthetic, you can even wear them with black skinny jeans if you’re confident about pulling off the tapered fit. To stay on the safe side, however, avoid pairing chunky trainers with denim, particularly straight-cut jeans, as you run the risk of sporting a full-on ‘90s dad aesthetic.


Wear the appropriate sneakers.

You may have seen style stars pull off riskier styles now and then, to favorable results. But unless you’re dripping with confidence, the rule is to pair dressier outfits with dressier shoes. You can never go wrong with a fundamental pairing—smart clothing like suits with refined leather sneakers, for example. With sturdy materials and a sleek shape, leather sneakers have a more polished and structured feel. Look for sneakers with simple silhouettes like the Common Projects Achilles or even the New Balance suede runners. These go well with office trousers, casual suits, and sport coats.

More: The Best Sneakers for Men, According to Sole Movement’s Martin David

Don’t be afraid to get your canvas trainers a little dirty.


Sneakerheads advise keeping those sneakers clean and pristine at all times, which is a sound and logical rule. But when you’re sporting a pair of Converse Jack Purcells, it’s perfectly fine when they’re a few shades cloudier than fresh-out-of-the-box white. Canvas trainers are generally made to look lived in, and nothing says broken in like sullying your pair quite a bit, if only to show that you and your footwear have been through some interesting times. Keep in mind, however, that gritty is different from muddy—filthy shoes are never OK.

Feel free to pin roll your jeans or khakis with low-cut sneakers.

If you’ve ever wanted to get that casual-cool look with pants and low-tops, then consider the art of pin rolling. The move, which puts those faded straight-leg jeans to good use, is a potential game-changer for your personal style. To pin roll, pinch the fabric at the hem of your pants between your thumb and forefinger. Next, fold the hem back along with the pinched fabric and then cuff as usual. This results in a clean and streamlined look.


Don’t wear visible socks.

This could be a potentially contentious rule, as there are instances when wearing socks that are anything but discreet works: Consider the uninterrupted visual of matching black joggers, black high-cut socks, and black high-tops. It’s an urban aesthetic that advanced streetwear enthusiasts have been nailing. But if you don't think you can pull it off, steer clear of visible socks, especially for low-top sneaks. You’re better off with no-show socks.

Go with what works for you.


What works on your friend may not work for you and vice-versa. Some shapes and styles work better on certain figures and silhouettes, or sometimes, it all boils down to personal preference when it comes to material and construction. Sneaker culture isn’t about coveting the most expensive sneakers; it’s all about finding what works for your needs and personal style.

Don’t fall for the hype.

Trends are fickle; they ebb and flow. While it’s good to get a new release now and then to include in your rotation, don’t feel like you need to splurge all the time for the newest sneakers, especially when they probably won’t suit you. It pays to consider your prospects, from fit and comfort to whether it suits your lifestyle, before handing over your cash.

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