I consulted a total pro to properly answer this question. Peter Papapetrou is a Toronto-based stylist says, “I’m a man, and 53, and fashionable. Adjusting your style later in life is a big deal.” Papapetrou, who does editorial and advertising gigs with the Plutino Group, was a TV style guru on CTV’s The Marilyn Denis Show. “A lot of my straight friends’ wives ask me what to do.”

Let’s dive into the leather jacket issue before we address the cowboy boots. “It’s a magic piece,” says Papapetrou. You can be the most basic underneath if you have a great topper. “Leather has an easy fit to it, it lasts, it molds well and it is iconically sexy.” That said, his advice is to keep things simple. Don’t do bells and whistles. “A black motorcycle jacket is timeless, but keep it clean; the fewer buckles the better.” Living in Canada, jackets and coats are paramount in any man’s wardrobe. Another great choice instead, he suggests, is the suede bomber. It works as long as the tones are neutral. “Taupe, khaki and sand tones are always classic.”

Critically, wrap your head around your age, he tells male clients. “Most guys have a set point in their head – usually back in their 20s – where they identified something as being sexy.” That set point, and that body, has changed; you have to work with the new measurements. “You do not want to look like a sausage!” says Papapetrou.

Get some professional help, suggests Papapetrou. “Most guys haven’t put in the time to see what works for them.” Hire a stylist, guys. Or work with a trusted salesperson at a good shop. Ask questions: “Does this work for me? Do I need something like this?”

Being fashionable does not matter to everyone. Being current should. Men tend to buy investment pieces, and not think about changing things up all the time. An excellent strategy. But it means adjusting colourways or cuts to look more modern at some point. “Sportswear is softer in colour for men right now,” he says, “and more relaxed in the cut.” 

Invest in classics, but if they are good pieces and they go “out”? Keep them (at the back of the closet, with my husband’s cowboy boots).

The main part of your wardrobe should be in the safe, neutral zone, so that it doesn’t need to be replaced as often: Think black, white, grey and navy. “Then fill in novelty items, with the current season’s colours,” Papapetrou says: things like T-shirts, polos or button-downs, as well as accessories. 

Stay on top of grooming! “You can look great from the neck down, but if your hair is not relevant, the whole look doesn’t work,” he says. A good haircut and regular nose and ear trims go a long way. 

Papapetrou has the same advice for men and women, and here at the Zoomerist we keep hitting this point: adjust, adjust, adjust. He tells the story of his own partner, who borrowed an Emporio Armani blazer for a Christmas party early in their relationship. “The sleeves on him were an inch and a half too long. He said there wasn’t any need to have them adjusted. He was wrong,” he says. “Every picture he saw, he gasped. It looked so off. It was a great lesson.”

The biggest thing guys don’t realize? “They don’t realize it takes work to look good.” It also takes work to stealthily suggest that a midlife-crisis purchase might have been a little too impulsive. But it is worth the effort to find the words, or the strategy, to encourage your man to put the work in. And if they really like that Affleck faux hawk or the tight leather jacket? Well, I say let them enjoy that indulgence. It’s cheaper than a convertible.

Always asking questions,

—Leanne Delap