How To Wear A Hat And Look Good

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“A lot of people say JFK killed the hat, because he was the first US president not to wear one at his inauguration,” says Nicolas Payne-Baader, an expert from Lock & Co Hatters.

“The reason for that was he looked awful in one. For a good-looking guy, he could not wear a hat...”

We’re talking about an accessory which, in the space of 80 years, has gone from an every day staple of men’s clothing to a statement piece associated only with eccentrics and annoying pop stars.

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Where many of the principles of men’s fashion haven’t changed since Edward VIII and the birth of tailoring, the role of the hat has done a complete u-turn, from a sure fire signifier of status and style to a novelty most men avoid at all costs.

“But even before JFK,” Nicolas continues, “the post-war years saw men’s clothing get a lot more casual. Hats were a scapegoat of that old Victorian conservatism, when you had whole generations press-ganged into uniforms.”

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He points out, quite rightly, that all our associations with hats are historical: from miners to cowboys to Frank Sinatra. But perhaps, like JFK, our real resistance to hats is the fact so many of us find them difficult to look good in.

“A hat changes your face so much more than any other garment,” agrees Nicolas. “It changes your whole immediate appearance massively, which is why a lot of men struggle.”

But for the sartorially adventurous, what the hat’s decline in popularity really represents is a further opportunity to develop their personal style. For Nicolas, the key is striking a contrast with the rest of your outfit.

“If I’m wearing something quite smart or smart casual, and I put on a traditional hat – a nice trilby or fedora – it will immediately make my overall look quite formal. If you pair a hat with something that it never would have gone with traditionally, you can get some great looks.”

In recent years, small, narrow-brimmed trilbys were fashionable (think Bruno Mars). The current hat trend, he says, is for high-crowned fedoras that are rounded out at the top.

If you’ve got a hunch you could go one better than Kennedy and want to take the plunge, we’ve asked Nicolas to talk use through 5 common types of hat and give us some styling and buying tips for each.


THE FEAR:
Looking like Pete Doherty. 

HOW TO DO IT RIGHT:
"The trilby is generally a medium to narrow-brimmed hat, that suits narrower faces. It is a good, casual, everyday hat that doesn’t make too much of a statement.

"When buying one, remember good felt hats are made of fur felt not wool. They hold the shape better and are more rain resistant and have better temperature control.

"Trilbys are probably not as high in the crown as you think they are. Men who have never worn a hat always try one on and think it’s really tall. It’s because they alter the shape of your head, and that takes some getting used to. You can always make it look shorter by putting a wider band on it.

"The most versatile colour for a trilby is brown. We sell brown far more than any other colour. Navy blue or grey will look immediately more formal. And avoid black hats –they tend to look quite funereal and imposing."



THE FEAR:
Being mistaken for a Mumford & Sons tribute act.

HOW TO DO IT RIGHT:
"Around Autumn time, I’ll wear a 8-piece tweed cap most days. When buying one, look out for good quality tweed, but it’s more important to get a colour that you like.

"I’d normally go for one that’s fairly plain rather than bright. Donegal tweed, salt and pepper tweed a simple herringbone work well – because there’s not too much going on with the pattern, they go with a lot of outfits. Mixing an 8-piece with a formal coat can look great.

"With a wool cap, fabric is important but even more so is the sizing. Remember: hats tend to shrink, not stretch to your head. If it feels a little tight in the shop, it’s probably too small."


THE FEAR:
The man from Del Monte, he say no.

HOW TO DO IT RIGHT:
“What you’re looking for in a panama straw hat is the quality and tightness of the weave. 

“Panamas come in a lot of different shapes and sizes. Wide brimmed ones generally suit a bigger face, while narrower panamas suit thinner faces.

“Style-wise, a traditional white panama with a black band is fairly formal, so if you pair it with, say, a battered linen suit, you’re going to look great. But it can look a little fussy if you’re wearing one with a brand new boating jacket.”



THE FEAR:
Looking like a Texan tourist. Or a tourist in Texas.

HOW TO DO IT RIGHT:
“This is a bold one! It tends to be big guys who are very confident in their image who want a cowboy hat. It can completely over-ride your outfit so you need to be prepared for that.

“With proper stetsons, you’re looking for the fur mix. A good one will usually be made from both rabbit and beaver. You can also get them in buffalo, which can be very expensive.

“America produced a mad array of shapes for this hat between the 20s and 50s, while English stetsosn tend to be more conservative.”


THE FEAR:
"Weren't you that guy from the New Radicals?"

HOW TO DO IT RIGHT:
“The official name for this is a bucket hat, but I labeled this the ‘Tong’ (after Pete Tong) after seeing so many kids wearing them at Glastonbury.

“They’re a really informal hat, but I quite like them – and they’re very popular.

“When buying one, you generally want a light cotton or a waterproof fabric. The beauty of them is that you can roll it up and stick it in your pocket.

“I think an older guy can pull one off too, but it’s tricky. I saw someone a while ago who wore one at an angle with a really nice beige mac, and somehow it worked. Sometimes, you just have to experiment.”


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MORE STYLE:
Tom Ford: What I've Learned 
What Esquire Wants For Christmas 
The Rant: Why You Should Give All Dresscodes A Miss 
***

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