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When is it okay to wear sneakers with a suit?

This is a look maybe only people like Justine Timberlake can pull off.

Monkey Business Images/Getty Images

The question

Sneakers with suits – is this really a thing?

The answer

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In the pages of fashion magazines, yes, it is. Ever since Justin Timberlake and Robert Downey Jr. started appearing on red carpets in this defiant getup, the big retailers have been hesitating about trying to push it on regular schlubs who aren't film directors or rock stars. The giant retailer J.Crew has been leading the charge on this, being so daring as to actually show catalogue images of impossibly young guys in super-tight-fitting suits with narrow ties and pocket squares and the trouser hems rolled up and leather or canvas tennis shoes proudly on display. And they look charmingly athletic and boyish. But they are always photographed on beaches and in social environments, not in life-insurance offices. As with many fantastical creatures – Hydras, Gorgons, Krakens, buses on Dufferin Street in Toronto – few scientists have ever observed them in the wild.

Certainly, you will see rappers and celebrity bloggers appearing in carefully styled pictures with bow ties and runners. And you will see stylish guys in downtown coffee shops wearing suits with sneakers and T-shirts or open-necked dress shirts, but never with a tie. These are resolutely casual outfits. In circumstances where formality is required – a funeral, for example – sneakers are going to look arch and glib.

Maybe in certain highly contrived environments – store openings, magazine launches, cocktail parties for publicists during film festivals – you might see people who have put on the full monty, a suit and tie and sneakers, but these are costumes for the event; it's rather like dressing as a fireman for Halloween. There are few actual jobs that would make such costumes feel natural. Maybe running an art gallery in Miami or an all-cardboard furniture store in Berlin or in, well, an actual sneaker store. You can't dress like this, yet, to work in an investment bank.

Actually, no, wait: I know someone who works for an online fine-art auction house in Manhattan. If you are him, go nuts. You can wear a giant zombie ant head if you want.

Here in Canada, there is a sneaker company pushing the move toward athletic shoes with fine wool: It is called Benjamin Daedfyshe and it is based in Toronto. They make some very attractive tennis-style casual shoes, including a dandyish red leather one (the scarlet Marlin) that I would like to own. Their catalogue shows guys in a hipster barber shop wearing these shoes and cool suits and getting their hair cut. The question remains: Is there anything else one can do in these outfits aside from getting one's hair cut in charmingly anachronistic surroundings?

I asked Patrick Cornish, the director of Benjamin Daedfyshe, whom he is selling this look to and he insisted that he has clients from three categories: (1) banker/lawyer types who slip their sneakers on at the end of the day to go out and party, (2) vaguely artsy industry people such as advertisers and (3) older men who have been wearing clunky leather shoes all their life and want a break. He sent me some pictures to prove it.

Soon, no doubt, there will come a time when the chief executive officers of the major banks will give their testimony before various government commissions of inquiry wearing Italian wool cut by English tailors and the coolest red tennis shoes. Until they do, I will wear my sneakers with jeans.

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Novelist Russell Smith's memoir, Blindsided, is available as a Kobo e-book. Have a style question? E-mail style@globeandmail.com.

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