How To Find Your Perfect Match

More specifically: what pants to wear with your sneakers.

“Do these go together?”

It’s a question asked rarely of a classic pairing like ham and pineapple, but when it comes to what sneakers go with what pants, for many of us, it’s relatively new ground. Sure, Jerry Seinfeld and Co were confident in their calls, but for those of us without a floor-length mirror at home, it’s always a bit of a roulette. As our appetite for new kicks grows, the question of what to wear the new-found loves with remains ever present.

We say go your own way (thanks Fleetwood) and wear it however the hell you like. Mainly because this is the way we’ve been playing it. But, in the interest of answering the questions that our editors have been fielding, we’ve pulled together some super loose guides – drawn largely from 5-hour stretches scrolling sneaker street style (hey, it’s called work Brenda). There’s a few do’s that we’ve picked up along the way.

So – how to best pair your kicks with your pants?

Thanks to Getty Images

Mr Big
If you’re a fan of the Dad Sneaker trend – they’re chunky, they’re sturdy, they’re hell comfortable – we hear you. These kicks are bold – and big – enough not to be lost in a wide leg. Play your pant style fast and loose. But wait, there’s more.

We also love a chunky sneaker with a loose fitting chino, cuffed and showing plenty of skin. It’s a cleaner look. Perfect for the block colours, the all-whites and the all-blacks.

And, while some may disagree, we firmly subscribe to the theory that Seinfeld was onto something – there’s no hesitation in pulling on a looser fit, early 00s style denim with your favourite Dad sneakers.

Play the blues
While we’re on the denim train of thought, it seems the pick for your everydays blues is street classics, something a little more streamlined. Thing clean-look silhouettes with plenty of cred. Converse, Vans, you know the drill. Old school style. Cuffing of hems is optional.

Thanks to @hypeflaw

Keep it sharp
Talk about a tailoring revolution. A blessing for sneakerheads worldover, the sneakers and tailored trousers combo is a look trend we’re main-lining on the daily. It’s clean cut and sports luxe and a really good time. But how to pull it off in a way that won’t see you get an ‘ahem’ from HR? Go for a shoe that’s quite luxe, something that won’t be mistaken for your ‘walk to work’ shoes. An all-white look. Or an all-over neutral. Work it.

Set to chill
Sweats are out favourite kind of pants (we’re still rejoicing these fall into the ‘office appropriate’ basket around these parts). Still they’ve got a bad rep as weekend-only wear. So, elevate your look. Go for something with a little more speed. A classic pair of Nikes, something low-key with a classic shape to keep it fresh. The Nike Cortez works well here, especially if you’re in the game for retro feels.