Style Debate: Can A Man Wear A Hat Without Looking Like A Tool?

Our fashion editors square up for a millinery-based head-to-head

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Can you wear a hat without looking like a twat? Yes. But that doesn't mean it's easy.

We’ve been wearing hats ever since Homo erectus put moss on his head to save a sun-blistered bonce. The collective penchant for millinery grew over the proceeding few million years until it reached a peak in the mid 20th Century. But since then our hats have slipped, and their popularity today is lower than ever.

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Therefore, over the past few years the only men wearing hats have been those with a penchant for serious menswear – those that sport suits on a regular basis, and cherish sartorial traditions. Men such as David Gandy. "There is something very old-school-gentleman-like about wearing a hat, especially a fedora or trilby," says the model and LC:M ambassador. "I personally adore hats, and wear one virtually every day. I wear baseball caps for motorsport and fedoras and trilbies around the city when it’s raining. The newsboy is what I wear most regularly; it’s the most versatile."

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It’s widely agreed that Mr. Gandy is one of the best-dressed men in Britain, so clearly, it’s possible to wear a hat and not look like an idiot.

However, I have a theory. It’s the 'one of the best-dressed men in Britain' thing that allows him to pull off wearing a hat. That is to say, you can only wear a fedora if your cool has already been established. Indiana Jones’ fedora looked good because he was a whip-toting treasure hunter; Don Draper’s trilby looks good because he’s a womanising alpha-male ad man and Colin Farrell’s beanie only looks good because his list of conquests is allegedly longer than the Irish coastline. 

To test this theory all you need to do is put a hat on, something with a nice wide brim, and let the condemnation begin. Then, quickly embark on an acting career, nab a couple of Oscars, try the hat again and gauge the response. There’ll be a marked difference, you’ll see.

Alternatively, you could transcend it all, go super retro and stick some moss on your head. Your bonce, at least, will be safe from the sun.

The examples of men looking good wearing hats in recent history can be counted on one hand.

Cary Grant in a fedora in North by Northwest is one. David Bowie, also in a fedora during his Thin White Duke period, another. Robert Redford in a Panama while filming The Great Gatsby is also a highlight.

That’s about it, though. Unless of course you count Paul Newman out shopping in a flat cap in 1959 – but that’s not really fair, the man would’ve looked good wearing a feathered fascinator: a claim no one else in history, all women included, can make.

The thing to remember is that the success of the majority of menswear trends can be attributed to an overarching function – unless a garment has a direct and clear purpose, it will pass like a kidney stone through the annals of style history.

Which means that unless you’re wearing your deerstalker on a trip to the Arctic to prevent your ears from falling off; a baseball cap to keep the sun off your face while playing… baseball; or a panama while on a yacht to avoid exposure, hats should be avoided altogether.

The reason? There is nothing more objectionable than a ‘personality accessory’. A few years back, for instance, there was a thing for personality pocket squares - little bits of jazzy fabric stuffed into jacket pockets to make the wearer of said jacket seem more interesting (the effect was, invariably, the opposite). The personality tiepin quickly followed.

The personality hat is perhaps the most insidious of these pandemics. Just look at Harry Styles’ catheter bag beanie, or Olly Murs’ pork pie silliness. Worn purely for the sake of it and providing no function other than preventing their wearers’ brains from evaporating, these hats are the antithesis of style and consequently must be avoided at all costs.

Unless you happen to be Jon Hamm, however, in which case please carry on. 


SEE ALSO: Is It Ever OK To Wear A Gilet?