Whether it’s the allure of Jon Ham, partially hidden under a front-tipped topper in Mad Men or Harrison Ford’s signature sable fedora (ft. some serious whip wielding bad-assery) in Indiana Jones—hats have a thing for the smart and stark…or vice versa.

You may be wondering why I’m choosing to write about such a seemingly inappropriate trend *weather* wise but I’m afraid you’re wrongly mislead. You see, we’ve been marketed to buy our chunky knits and “break out the woolies” come fall but in fact, wool hats are probably more seasonally comfortable than your monogrammed snapback (if people even wear those anymore?).

Wool actually clematises to hot or cold temps and absorbs moisture more than other textiles…in other words, you won’t need to be wiping your forehead over and over and over. I suppose my case is also justified on account of the wide-brimmed chapeau housing your head from the sun.

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All that said and done, a hat reveals more than you think. It’s a standout style, meaning you’ll do anything but hide beneath it and therefore, takes a certain kind of confidence and charm to really flaunt the full Pharrell-effect.

Here’s how to wear it right.

1. Take social cues from your Grandfather’s fedora: Chivalry isn’t dead after all, it just suffered from temporary amnesia the last time you forgot to take your hat off at your gf’s parents house. I’m all for sporting it indoors as a part of “the look” but it’s all in the subtle gestures—i.e. removing it when opening the door for someone, when meeting someone new, etc etc.

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Image Courtesy: Steven Onoja

2. The more bones, the better: Please, I know it’s Jays season but enough with the ball caps outside the stadium. Normcore is no longer; “athleisure” will never be a thing as hard as it tries. The more hand-crafted vibe it beholds, as if custom designed by a milliner, the more you embody some Sinatra swing.

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3. Justin Timberlake > Justin Bieber: Our beloved JT is known for sporting a signature trilby, suiting his face shape and head size accurately. Where as JB opts for toppers of larger widths that sit half-placed on his head. Clearly wind (or outside elements of any kind) is not a factor when you’ve got a private jet awaiting. In the end, we want the charisma of someone who takes their Grandma to lunch prior to spending a romantic evening overlooking river Thames. You can forgo the poor hattitude of an image-driven child star with too much money to handle at the door.

Influencer Jenn McNaughton identifies and interprets fashion trends and inspirations of the moment, with a nod to where they’re coming from and how to make them your own.