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“Rules are meant to be broken,” is one of those sayings that, while occasionally true, can often lead to trouble (just ask Canada Revenue). Wearing white jeans in February or a leather cowboy hat at any time of year may not carry the same kind of penalty as declaring your cat as a dependent, but it’s still not for everyone. For those who wish to err on the side of caution, rules governing men’s fashion serve as valuable guidelines to keep us looking good without spending hours deciding what to wear.

Like the tax code, the rules of summer style are a mix of practical common sense and puzzling esoterica, and they benefit from an update every decade or two. Take note of these revisions to the longstanding dictates of summer men’s wear and dress without fear (as long as you leave the cowboy hat at home).

Sock it to sandals

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“As for cautionary edicts, there is only one. Sandals are not properly worn with socks.” So declared John Berendt in the June, 1984, issue of Esquire.

While socks have been worn with sandals since ancient Egyptian times, for most of the past century the only people doing so were dads, NBA players and people at Phish shows – groups known mostly for their love of loose-fitting, comfortable clothes and general disregard for fashion. Now, thanks to a booming selection of fashionable sports wear and the burgeoning “dad core” trend, people everywhere are discovering the previously unknown pleasures of socked, sandalled feet.

As Esquire’s Berendt rightly notes, the purpose of sandals is to keep your feet cool, so wearing socks and sandals doesn’t really make sense in the height of summer. But even he, perhaps, couldn’t have conceived of a pair of cheeky Balenciaga slides or matte-black Rick Owens Birkenstocks, both of which look perfectly fine with a fresh pair of cotton socks.

Wear brown in town

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Like many of Canada’s strange cultural mores (robe-wearing lawyers, Boxing Day), we have the Brits to thank for the archaic tradition of forbidding brown shoes with a business suit.

According to a 2016 study by Britain’s Social Mobility Commission, not only is it still very much frowned upon in the U.K., wearing brown shoes can be a serious impediment to doing business there. “It is shocking, for example, that some investment bank managers still judge candidates on whether they wear brown shoes with a suit, rather on than their skills and potential,” said the commission’s chair Alan Milburn, clearly scandalized. If you live in London and work in finance, play it safe and opt for a pair of sturdy black Church’s polished to a mirror-like shine.

In Canada and everywhere else, a nice brown woven tassel loafer or monk-strap can do wonders for punching up a blue or grey suit in summertime.

Free the ankle

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The sight of a man’s bare ankle beneath the cuff of his trouser used to be cause for scandal, akin to delivering a presentation with your fly down. “Nothing robs you of credibility more than the sight of a bare leg when you cross your legs,” wrote William Thourlby in 1980’s You Are What You Wear.

While calf-length socks are still mostly necessary for office wear, going without is now perfectly fine for less buttoned-down occasions. While the sockless look was popularized by Milanese dandies, you don’t need a hand-rolled cigarette or a Vespa to pull it off (although an immaculately-tailored suit and a nice pair of shoes will get you most of the way there).

For anyone who doesn’t enjoy the sensation of a sweaty foot against damp calfskin, low-profile socks will save your feet from your shoes (and vice versa), while maintaining an air of Italian sprezzatura.

Do yourself a solid

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“Nothing’s gained by trying to build false security about mixing patterns,” wrote Charles Hix in his 1978 instructional tome, Dressing Right. “It’s hard. But worth it.”

Forty years later, men are still grappling with the intricacies of combining striped ties with checked shirts. If you are among this legion, fashion is now on your side: Just wear solids. While once considered the definition of squareness, wearing strictly solid colours can look just as good or better than advanced peacocking involving multiple contrasting fabrics.

A colour-blocked ensemble starts with a larger piece like trousers or a jacket in a safe, steady tone, then adds accents in complementary colours (a tan jacket with a burgundy T-shirt, say). For a more advanced tone-on-tone look, choose pieces in slightly different shades of the same colour (blue is a good place to start) and varying textures.

Stand on guard for the Canadian tuxedo

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It is possible to have too much of a good thing. So goes the thinking, one must suppose, behind the longstanding prejudice against wearing jeans and a denim top at the same time.

As the story goes, the look entered the world of fashion in 1951 when Bing Crosby was barred from a posh Vancouver hotel because he was dressed in jeans. In response, Levi’s made the crooner an actual denim tuxedo jacket, which he wore extensively. A quarter-century later, attitudes hadn’t changed all that much, according to the 1975 handbook Dress for Success, by John T. Molloy. “Denim shirts are suitable for some men in some professions,” he wrote. “If you’re not sure you should wear them, don’t.”

Fortunately, dress codes have relaxed considerably since Crosby’s days, making a well-executed denim-on-denim look completely acceptable for check-in at even the poshest of hotels. About time, too.

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