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TORONTO, ONTARIO: Feb. 18, 2016 - Jeremy Freed. (Tim Fraser for The Globe and Mail) (For Style story by n/a )Tim Fraser/The Globe and Mail

I might have known something was wrong sooner, but such is the case with regrets: I thought I looked great. It was coming on winter, and I knew I was unprepared, so I headed to my local Mountain Equipment Co-op to sort myself out.

I wasn't inclined to spend top dollar, but I found something down-filled in my price range that had both a hood and insulated pockets, key features for blizzard season. It was also reasonably stylish: a standardcut parka in a colour that made a statement. Toting it home I felt both pleased with myself and prepared for the worst winter could do.

At home I texted a picture of myself in my new coat to my parents who had been concerned that I wouldn't be warm enough this season. "Lovely!" my mom texted back, followed by, "It's very bright, isn't it?" My mother doesn't understand fashion, so I hadn't expected her to grasp the coat's appeal. It was very bright, though, and puffy, and while its shade was more akin to golden yellow than hazard-sign, her comment prompted me to have a fleeting doubt about my purchase.

In practical terms the coat was terrific. No matter what I wore underneath, its copious down kept me warm on the coldest days, whether trudging to work over icy sidewalks or waiting for a late-night streetcar. Sure, it was eye-catching, but I liked the statement it made: "Bring it on, winter! I'm ready for ya."

Then, walking up my street one bright winter morning I passed a boy and his mother out shovelling snow. "Mom, that man looks like a banana!" the child said. I was a couple of houses down by this point, but his voice carried as cleanly as February wind chill through a pair of cheap cotton slacks. His words cut deep because the little boy spoke the truth. I looked ridiculous.

Who among us has not made a fashion mistake or two? I have likely made more than that, but the tale of the banana coat is the worst because I should have known better. I do know better now: There are ways, I have since discovered, to avoid buyer's remorse altogether.

"It happens to me all the time," says Ethan Song, co-founder and creative director of Montreal-based men's-wear brand Frank & Oak. "I get excited about things, and then I realize it's something that doesn't fit with my personality, or was just a trend I wanted to buy into." Song describes the pair of pricey Nike Jordans he bought on a whim that have been gathering dust in his closet ever since. "I'm a big fan of Jordans. I wanted to buy into it, but it's just not part of my aesthetic."

Song advises buying things like denim, sweaters and outerwear in navy, grey or black as part of a foundation of simple basics – a heather grey merino sweater, a couple pairs of dark jeans, white oxford shirts, a topcoat – and then adding more fashion-forward pieces to the mix. "I think the recipe for most guys is maybe 70 per cent timeless and 30 per cent what's in season."

That was all sensible advice, but the problem now was that I didn't trust my instincts. I had paid good money for a coat that made me look like a piece of tropical fruit. "Just look at men who are known for timeless style and get inspired by that to put together your look," says Song, citing Bob Dylan and Steve McQueen as good examples. McQueen would never have worn the yellow parka. For more dire cases Song advises retaining the services of stylist.

"I once bought this hideous Adidas David Beckham track-suit jacket," says Leo Petaccia, owner of Two Dudes Shopping Co., a men's personal styling agency. Petaccia adds that this incident took place a decade before he shopped for clients professionally. "I was such an idiot, not to mention a sucker for marketing."

Petaccia describes an awful-sounding warm-up jacket with dragon embroidery and metallic appliques. It was a valuable learning experience, he says, teaching him to see past marketing gimmicks and to consider new purchases through the lens of his overall look. "Picturing if it suits the rest of my wardrobe has paid dividends," he says.

I was able to get through this past season by layering various sweaters, down vests and technical shells, but I know the time will come when I'll have to head out again in search of new outerwear. The value of mistakes is what we learn from them and I've learned several things from this one: Think of McQueen, consider the rest of my wardrobe and, most importantly, don't buy a parka that's not grey, black or navy.

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