Stylish or try-hard?

Stylish or try-hard? Photo: iStock

I've never really understood hats as an accessory. Maybe it comes from when I was a kid and my mother used to always say you can't trust drivers who wear them. Or it could just be the fact that I have such a huge head that every time I tried to wear one it looked as though I had raided a five-year-old's dress-up box and was trying to play grown-ups.

Either way, whether it's a baseball cap, fedora, “poor boy” or even a Panama at the beach, my aversion to wearing them has become akin to a phobia. And while I do respect the man who can pull off a hat as a fashion accessory, I often question whether the guy wearing it actually looks as good as he thinks he does.

The funny thing about hats is that they can either make or break the way you look. Ergo, the way people perceive you. For example, in a recent Executive Style article that touched on the topic of creating a personal brand or style to get noticed, one article subject's signature look included a trucker cap. It was part of his look, or aesthetic, yet it was also a lightning rod on the accompanying comment forum for sniggering, dismissive one-liners. 'Bogan', 'redneck', and even 'dated' were among some of the more charitable decscriptions - just because of the hat this guy likes to wear.

It's not just trucker caps coming under scrutiny and social criticism.

The fedora – once a staple of any man's wardrobe and one worn with pride – is an 'avoid at all costs' signal for some women. Blogs like this one and articles like this are dedicated to the naming and shaming of men from online dating sites who wear, and in some cases collect, fedoras. The owners clearly see their hat as an extension of their personality, one that is outgoing and stylish. Unfortunately it's sometimes perceived by others to highlight someone who is a bit of a dick, and even harbouring unhealthy attitudes towards women into the bargain.

The latter is the hypothesis of Benjamin Abraham, a writer and academic at the University of Western Sydney who has recently written a paper on the presence of the fedora in pop culture and the male stereotype.

“The backlash, I think, is explained by the fedora's association with PUA, or pick-up artist culture,” says Abraham, “which is one of the most misogynistic and horrid cultures around. It sees women as 'fair game' because, duh, how else is a guy going to get laid in this day and age?”

Abraham says a key element of PUA ethos is about appearance, and a hat is a key visual differentiator. An online PUA 'style guide' from 2009 stated that: "If you wear a hat, make it memorable, easy to spot, and something to work with your style. This is usually easier than it sounds. Try the fedora ... it portrays you're a stylish man that knows what he's doing, and it's a great lock-in prop."

And while there are some definite benefits to locking in a hat every now and then - such as when you're as hung over as sailor on shore leave and haven't showered for three days, or for protecting you from skin cancer - it is undeniable that hats are an attention-grabbing accessory. Just ask Bob Katter.

What kind of hats do you think are acceptable for men to wear?