Written by Katrina Garofalo

Have you ever embarked on your day wearing something — a bold pair of pants, perhaps — that you know are a “risk” but you love anyway? If you haven’t, I’ll describe the feeling for you. It’s like finding your favourite nail polish on sale. It’s akin to waking up to see the pimple you went to sleep with has completely disappeared. Like you’re the dorky main character in a movie montage that’s been transformed into an elegant leading lady at the hands of either very best friends or professional stylish people. You all look at each other and nod knowingly at a job well done. Then you leave the comfort of your house only to immediately regret wearing the pants.

Taking risks is simultaneously the best and worst thing ever. There is no other way to put it. No matter the articles you read or the editorials you peruse, confidence can slip away with one sideways glance from a stranger in public. Chalk it up to anxiety, insecurity, people-pleasing, or my favourite — all of the above.

There are some obvious ways of working up to taking risks or at least working around them, the main one being to follow trends. Trends are supposed to be a safe house. Sure, they can be a little boring and predictable at times, but if everyone is wearing the same weird pants it makes them slightly more acceptable, no? Unfortunately, not. Trends are all fine and dandy until one particularly interesting one grows legs and makes a run for it. There are few things more painful than watching people mistakenly chase after “trends” that were never meant to be trends in the first place. The “wet look”, super-daring cut outs, every makeup idea birthed from Instagram, lingerie as daywear, clear plastic footwear…you get the idea. So many non-trend trends were a moment of inspired creativity, meant to be appreciated in the moment. With every fashion week cycle, I dread the tabloid-esque coverage of “runway trends to try” because more often then not, what happens on the runway is meant to stay on the runway.

It makes me wonder whether this erroneous understanding of fashion “trends” is to blame for the slow and steady disappearance of haute couture runway shows. Of giant feathered headdresses, gowns with layers of nothing but tulle from the neck down, and shoes that are meant to look like lobster claws. But, I digress. Some aspects of fashion or style or creative expression are not meant for the masses to follow. When they are followed, it can lead you astray.

I’ve gone so far as to consider the possibility that this style anxiety is a Canadian issue. Canada is known for kindness, cold weather, and maple treats but nowhere in the world is there less of a concentration on style than the Great White North. In the June 2016 issue of the Globe Style Advisor, Danielle Meder describes Canadian men’s style as “adorably oblivious” for good reason. If we aren’t surrounded by fantastic style, it’s not hard to believe that we aren’t dressing to the nines on the daily. We are creatures of habit, after all. Even Garance Doré noticed the strange Canadian way of life, and she was in the country for less than a week.

Thinking through these risk taking, personal style, anxiety ridden questions is no easy feat. So, here’s the working conclusion I’ve come to: personal style is challenging for everyone. There is not one person who wakes up feeling totally and completely secure in all their decisions, sartorial or otherwise. There is great value in the uneasiness and doubt that are part of the process of discovering your personal style. And risks are where it’s made.