The age old question that has plagued men for years – can, or really should men wear hats?

I’m not talking about beanies (toques), ball caps or even flat caps, but proper brimmed hats that the dapper gentlemen wore back in the days where everyone wore suits for even the most causal of outings.

Any chance I could look this cool? Prob not.

Times have changed, as have the fashions. Now there are five types of men who wear hats:

• Hipsters
• Super cool people who have a ton of confidence
• Cool old gents
• Farmers
• People who shouldn’t wear hats

Which one am I?

I went to my local hat store in Yaletown to find out.

The Goorin Bros. Hat Shop in Yaletown, BC was quiet and smelled like wool and leather. The couple at the counter were just paying for their hats in preparation for a much-anticipated vacation, I overheard.

Once they’d left, I was greeted by Maddie. She had green hair and a fedora. She looked like she’d know what was stylish and what I definitely shouldn’t wear on my comparatively boring head.

I explained how I’ve never really been able to wear a proper hat due to lack of style, confidence and having a deceivingly large skull. Seriously, it’s huge and in the recent snow, it got very cold.

My head got so cold on the snowy walk from work.

We went through all sorts of hats, from treated, wide brimmed ones that were perfect for camping or being outdoors in a typical rainy Vancouver Spring or Fall, to wool fedoras that would suit a well-deserved musician more than me.

Swing and a miss. Next!

Nobody mentioned the short-brimmed Trilby hats and rightly so.

I love the idea of wearing a hat more than my confidence allows, but Maddie told me she used to think the same way. After some wearing around of her new hats, of which she has many, they became part of her wardrobe. Her confidence grew and now she loves them.

I’d be more comfortable wearing a hat if it were for more practical reasons. That’s why I really like the coated Grenadier. In my pea-coat I look a little like an archaeologist-professor (but far less cool), but it might suit in something less formal.

The flat cap is something much less obvious and trying hard to be stylish, while combining practicality and completing an outfit. This black one was also treated for the rain and had little ear flaps that can fold out in the worst of weather.

What’s it to be then? Something purely practical or a little more trendy?

The best piece of advice was that “If there’s something really calling to you, then get it. Then if you’re still unsure, wear it around a bit and see how you feel.” I know that sounds obvious, but I’ve never been able to wear a hat without it being part of a costume. Maybe I should just take the plunge.

Which one should I get? I’m going to head back in next week and pick one out.

Are you a hat-lover or aren’t you convinced? Go and try some on before you make your mind up.

Note: This post is entirely my own opinion and I’d love to thank Maddie for putting up with my insecurities and ridiculous questions.

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