Get Your Kicks: A Grown Man’s Guide to Sneakers

You might have noticed that sneakers are back in a big way. At every turn, they’re outfoxing their hard-bottomed brethren: slip-on kicks are displacing penny loafers; vintage runners are beating out brogues. But it’s been a minute since you’ve worn a pair of sneaks outside the gym — you could use a refresher. That’s where we come in.

Below, we’ve rounded up the badass pairs you need to start your collection, the up-and-coming labels that should be on your radar, and a few quick rules for working ’em into your wardrobe. In no time flat, you’ll be turning heads and gaining street cred with your footwear all over town.

Essentials from the Experts

We chopped it up with three of Toronto’s biggest sneakerheads to get the lowdown on their must-have kicks. Here’s what they told us to buy.

Joel Reilly, Community 54

Joel Reilly Community 54
Adidas Ultra Boost

Adidas Ultraboost

Some call it the most comfortable shoe of all time, and it just might be. Thanks to its tonal knit upper and handsome thick mid-sole, this high-tech runner will take your sportswear game to an entirely new level.

Nike Air Max 1

Air Max 1 The 6

Tinker Hatfield, the godfather of sneaker design, designed this sleek trainer after seeing the Centre Georges Pompidou in Paris. Enough said. Start with the Toronto-inspired “The 6” edition above, and collect from there.

New Balance 998

New Balance 998

This American-made runner is a must-have for any man looking for a retro silhouette with personality. Rock ’em with a business casual outfit on Friday — they’ll lend a welcome hit of offbeat, effortless style.

Adidas Stan Smith


If you don’t already own a pair of Stans, shame on you. Named after the former No. 1 American tennis player, these legendary sneakers have enough polished charm and minimalist appeal to stand up to even the dressiest tailored garb in your wardrobe.

Tristan Banning, Sidewalk Hustle

Tristian Banning Sidewalk Hustle

Converse All-Star Chuck Taylor

Converse Chuck Taylor

They’re perhaps the most uncomfortable shoe on earth, but that doesn’t matter. Chucks remain the ultimate “cool guy” status symbol across the world. They look just as good paired with beat-to-shit jeans as they do with a bespoke flannel suit.

Nike Air Max 90

Nike Air Max 90 Infared

A good “shit-kicker”, these timeless sneakers — beloved by everyone from 2Pac to LeBron — will give you a touch of street credibility with their iconic air cushion heels and flashy colourways.


Yeezy Boost Jordan III

Every man needs one pair of truly unique sneakers. Something that’s near-impossible to acquire. Whether it’s a pair of Kanye West’s much-hyped Yeezy Boosts or some limited edition Air Jordans, it’s the exclusive releases that real sneakerheads live for.

Takuya Morioka, CAPSULE

Takuya Morioka CAPSULE

Nike Air Force One  

Nike Air Force One

Best paired with a slim-tapered pant, these bad boy sneakers have come a long way from Nelly’s Billboard topping hit. Pick ’em up in either white or black for a look that’ll never lose its cool.

Nike Air Huarache

Nike Air Huarache

Even stripped of the loud colours it’s typically adorned in, this tech-savvy sneaker is bold and insanely comfortable, thanks to a neoprene upper that feels like a state-of-the-art sock. It’ll punch up just about any casual ensemble.

Buddy Bull Terrier Low

Buddy Bull Terrier Low

If you’re a man with refined tastes, these sneakers from Japan’s Buddy are comfortable, understated and undeniably classic.

4 Luxury Brands You Should Know

There’s more to life than Swooshes and Stripes. The fashion-forward kicks from these on-the-rise labels are well worth investing in.

Hender Scheme

Hender Scheme

The handcrafted kicks from this buzzed-about Japanese line reinterpret the most iconic silhouettes in sneaker history — from Vans Authentics and Nike Air Prestos to the Air Jordan IVs above  — in gorgeous natural leathers that will age and darken beautifully over time.

Filling Pieces

Filling Pieces

Originally trained as an architect, Amsterdam-bred designer Guillaume Philibert’s rising footwear line is heavy on strong, contemporary lines.

Article Number 

Article Number

Roam the streets of LA, and you’ll spot these everywhere. Article Number is a burgeoning sneaker brand that puts a luxurious, high fashion spin on street footwear.

Common Projects

Common Projects

Every wondered what would happen if you crossed the effortless good looks of a tennis shoe with the pedigree of a bench-made brogue? Here’s your answer. Common Projects hand-stitches their lush kicks in Italy using the finest Nappa leathers.

How To Pull ‘Em Off Right


The Perfect Pants: You want to show off your kicks, right? Then stop drowning ‘em under baggy, formless bottoms. For maximum effect, stick to jeans and trousers that are tapered through the leg and end right at your ankles. If you’re a fan of cuffing your denim, make sure to employ a tight, clean pinroll.

Suit Up: Sneakers and suits are a match made in heaven — as long as you’re wearing the right kind of sneakers. Keep things as simple and classic as possible, like a pair of low-top tennis shoes (Stan Smiths or Common Projects will do nicely) or ’70s-era runners (like New Balance 574s). Avoid bright colours and tech-y details like the plague.

Tone It Down: With few exceptions, there should really be no more than two dominant colours on your sneakers (a highlight pop here or there is OK). You want to be able to actually wear these things, and not be stuck wondering what matches with purple, yellow and teal.

Ball Isn’t Life: Modern basketball shoes — i.e. virtually anything you’d see worn during an NBA game this season — should never be worn off the court. Generally speaking, they’re garish and clunky and unrefined. If you want to pay homage to your love of the game, do it by wearing a pair of throwback Jordans or Air Force Ones; leave the LeBrons to your kids.