The Hat: A “How To” Guide

Johnny Depp

It’s that time of year when, we not only do we start turning on the heating, renew our penchant for overcoats and take a liking to stodgy grub, but also when every male of good standing finds himself in search of a new cap or hat.

Having carelessly left my faithful tweed herringbone Stetson Baker Boy on the tube one recent afternoon, I’m on the hunt for a new hat myself.

Of course, this particular hat suited my head, was not ostentatious and was, what I call a mild mannered style statement, which is what all headgear should be because, as soon one looks like one is off to a fancy dress party, the game is lost.

A hat must look as if it’s always been worn there (on one’s head) and is no momentary affectation. It should fit your head as well as your hair and look completely natural.

As my old pal, former Clash bassist and legendary hat wearer Paul Simonon said on Saturday, “You should wear a hat. It should not wear you.”

Indeed, I’ve always been partial to a hat but am aware that certain styles are not partial to me. Consequently, as far as headwear goes what suits one chap might certainly not suit another.

We all have different shaped heads and faces so I would advise never to buy headgear online as you have to literally try on a hat or cap. It is also best not to buy on impulse or ever wear a novelty item. But to be fair, some men look awful in most hats while some look great in any.

As such, a hat that suits is a true gift that every man should cherish; so, if you find a style that suits you, best stick with it and avoid those that don’t. Hats, like glasses, are the first thing people see and take note of, so you must get it right!

But the question still remains:  what hat should one buy?

The Pork Pie Hat

The chosen head gear of the common or garden hep cat- whether it be Buster Keaton, Malcolm X, Popeye Doyle (Gene Hackman) in The French Connection or Tom Waits – this truly iconic hat is so named because the crown is shaped exactly like ye olde English Pork Pie.

Actor Gene Hackman wears a Pork Pie hat as Jimmy "Popeye" Doyle in the French Connection.
Actor Gene Hackman wears a Pork Pie hat as Jimmy “Popeye” Doyle in the French Connection.

It first appeared in the UK in the 1820’s, was popular in New York in the 1900’s and subsequently became the only hat for US jazz artists from the `40s through the`70s, its most famous devotee being the great saxophonist, Lester Young.

In the following decade it was the chosen headgear for Jamaican Rude Boys, UK skinheads and US soul, rhythm n’ blues and jazz artists, all of whom favoured the stingy (1 or 2 inch) brim.

Consequently, via the Two Tone revival, it appeared again in the late `70s and was huge amongst urban jazz groovers who read The Face Magazine in the`80s and, of late, was sported by Mr. Heiselberg in Breaking Bad.

The porkpie, whether in felt or essential summer straw is a class act. Two very fine versions are available in London at Lairds at a mere £85.00 and Locke & Co. at £225.00.

The Baker Boy Cap

The seven panelled Baker Boy or newsboy cap with the button at centre crown is a hardy perennial. It was first embraced in the US by (news) paper boys, working class labourers and street toughs until, by the`20s, was all the rage as a casual alternative to the Fedora or Derby and slipped nicely into the Jazz age.

David Beckham shows off his baker boy hat
David Beckham sports a Baker Boy hat on a night out.

Meanwhile, in the UK it became standard mufti for Geordie coal miners who accessorised it with a collarless shirt and the odd blue scar and gangsters such as The Peaky Blinders who stuck razor blades in the cap’s peak.

Consequently, the item remained firmly in the hands of the working classes but, as men took to Brylcreem and rock n’ roll in the fifties, it graced only the heads of old men and schoolboys.

The cap returned in the seventies via the Gatsby revival where fashionable-types aped `20s styles until it grew out of all proportion, and was adopted by glam rock fans and faded into obscurity.

Of late , the Baker Boy is back on the street in force. Stetson produces fine examples named Hatteras in tweed or linen that are available from American Classics will set you back £69.50,  Lock & Co’s perfectly balanced cap in Muirfield tweed is £99.00 while Mark Powell’s elegant Gatsby in black and grey is £99.00.

The Homburg Hat

The Homburg has made a huge comeback and it looks great with all kinds of kit. Simply, it’s a heavy felt hat characterised by its ‘kettle curl’ stiff brim, its edge bound in grosgrain silk and a deep  “gutter vent,’ running down the crown.

Wearing a Homburg hat Benedict Cumberbatch is a great actor
Benedict Cumberbatch wears a Homburg hat.

It’s the hat that Orson Welles sported in The Third Man, Albert Steptoe in the 70’s TV show, Steptoe and Son, Winston Churchill, Dwight D. Eisenhower and Al Pacino in Godfather 2 and originated from Bad Homburg in Germany where it was first discovered and then popularised by Edward VII in 1907.

Of course, today the hat is uber cool, a cracking version from Lock & Co is £285.00, Bates’ soft rendering comes in at £270.00, while Laird’s truly desirable hat is £245.00, Christy’s is just £125.00 while Mark Powell’s Homburg – probably the most stylish and the best value- is £95.00

The Short Snap Brim Trilby Hat

Not to be confused with the pork pie this hat, as worn by Johnny Boy (Robert De Niro) in Mean Streets and RAP legends Run DMC, has a small, “stingy” brim and a high concave crown.

Frank Sinatra & Dean Martin wear their trilbys.
Dean Martin and Frank Sinatra both wearing Trilby hats.

Favoured by `60s American soul artists, it was also big amongst the likes of Sinatra Bogart, Dean Martin and,  particularly, English movie stars such as Trevor Howard, Dirk Bogarde and Noel Coward.

Its name comes from the stage adaptation of George Du Maurier’s 1894 stage play Trilby – the style worn by its lead character – after which the hat was adopted by well to do horse racing-types, who passed it onto racecourse spivs and movie stars such as until, by the `50s, it was de rigueur for Brit ne’er do wells.

The hat disappeared from trendy heads in the`60s and didn’t appear again until the`80s as part of retro vogue. Recently, the hat, which was adopted by Kate Moss and a bevy of US rappers, was consequently badly reproduced in straw and paper and became rather naff.

Still a fine example by the likes of Laird (who do a Sinatra Trilby for £165) will always look great especially when teamed with the right outfit.

The Flat Cap

Perhaps the most precarious of all caps, this item has to be approached with due caution. I favour the style constructed from one piece of material stretched over the crown and never three pieces sewn together which is the hallmark of the recent cheap imitations and have a brim that looks like a duck’s bill.

Prince Charles looks good in a flat caop
His Royal Highness, Prince Charles wears a flat cap.

The hat was born in 1571 after an Act of Parliament in the UK -used to stimulate domestic wool consumption – ordered that on Sundays and holidays all males over 6 years of age, except for the nobility and “persons of degree,” had to wear said woolen caps and were fined for not doing so.

And the tradition carried on amongst the hoi polloi the cap becoming a de facto uniform for Welsh miners (who called it a Dai cap) and Manchester street gangs whilst English toffs donned them with tweeds in the country or with champers at the racetrack.

The hat all but vanished by the seventies, elderly Welsh man, London cabbies and wide boys excepted, and only reappeared in the eighties when US rap acts took to the Kangol stretch version. Since then it has been a hip- hop stalwart but still looks best worn a la Cuban émigré style with Guayabero and chinos. For winter I’d go for a Christy’s translation at £39.00 or, if flush, Bates’ cashmere tweed at £135.00.

The Beret

A much maligned item that has reared its head again as sported by the likes of yours truly, Christos Tolera and Kevin Rowland, this is the simplest of hats that can look great or absolutely awful.

Alain Delon is a French actor who wore a beret
Classic French Style: Alain Delon wears a traditional beret in the 1960s.

Made from one piece of felt, a beret looks best when shrunk to fit ones head.  A purely French item, it was Warsaw born Jacques Spreiregen, founder of Kangol (name was derived from K for knitting, ANG for Angora and OL for wool) who, on his return to civilian life in London after WW1 in 1918 turned to importing Basque berets and then producing them (which they still do today).

Subsequently, the beret was popularised by the Prince of Wales, Clark Gable, Picasso and Douglas Fairbanks. In the `30s the UK armed forces prescribed the beret after tank regiments found them perfect for wearing headphones.  Cheap, foldable and convenient, they soon spread throughout the armed forces worldwide its most famous patron being General Montgomery.

In WW2 the beret was adopted by the French Resistance as a symbol of French nationalism. Their surplus after the war provided style for the common or garden beatnik. With anti-establishment undertones, Che Guevara famously gave the item a whole new lease on life.

Others whom have commandeered the beret-look include The Black Panthers, Johnny Rotten, Madonna and Samuel Jackson so maybe there is still life in the old felt yet.

Forget about these hats as they are unlikely to flatter you:

The Panama Hat

No matter how arty and esoteric you think you might look in a big brimmed Panama (actually invented and usually manufactured in Ecuador) it will simply make you look like a fellow who doesn’t own a mirror.

The Fedora Hat

Another expansively brimmed hat that looks ridiculous on most men. It is usually worn by  ‘lovey’ elderly actors and fans of opera who also love a neck scarf.

The Baseball Cap 

No man over 21 who isn’t at a baseball game should ever entertain such nonsense. The domain of misled teenagers and hip hop fans who really want you to know that they own a Kanye West recording, baseball caps are neither clever nor grown up.

The Bucket Hat

Not even Liam Gallagher can crack this nut. A supremely Ned hat, it should only be worn when you are either badly sun burnt or are fishing – preferably both at the same time.

The Rasta Hat

Absolutely fine if you are a devotee of the Rastafarian faith, black and sport dreadlocks. White men however should never even think about wearing such a hat or, for that matter, growing locks. Get a life.

The Bowler Hat

Still fine for special occasions requiring formal dress, the bowler hat was once the preserve of City executives and the genteel, but now seems to be worn most regularly by doormen at members clubs and restaurants.  ML

Lock & Co.

http: //

Laird London

American Classics

Kangol Store