Esquire (UK) - - Style - with Teo van den Broeke

Dear Sir,

Get ahead, they say, get a hat. Or at least, that’s what they used to say. But times have changed, and bowlers and tit­fers and the rest have gone the way of all things.

And what I want to know is which hat to get? OK, I un­der­stand that in in­tense sun­shine it can be an idea to cover one’s head. And that there are straw things for that. And in sub-zero con­di­tions a hat makes sense, too. And you can buy woolly things for that. But the rest of the time, when it’s merely mild, or just a bit nippy, I’m bam­boo­zled. Is there a hat that is ac­cept­able for the stylish modern man to wear that doesn’t look like a des­per­ate at­tempt to cover a bald patch? Should I bow to the in­evitable and buy one of those Amer­i­can base­ball caps? Some­times I wish I was a cow­boy or a chef or a bishop. Their hats come with the job. But I’m not one of those. I’m a loss ad­juster. With a comb-over. Ber­trand, Hack­ney, Lon­don The thing about hats, Ber­trand, is like most things in menswear, un­less they’re serv­ing a very spe­cific func­tion (sig­ni­fy­ing your bish­opric, for in­stance, or keep­ing the Ari­zona sun off your heifer­herd­ing face), they’re su­per­flu­ous to re­quire­ments. Hats worn purely for “style”, in my opin­ion, are noth­ing more than af­fec­ta­tion, and, as John Locke put it: “af­fec­ta­tion is an awk­ward and forced im­i­ta­tion of what should be gen­uine and easy, want­ing the beauty that ac­com­pa­nies what is nat­u­ral.”

There are, as with all things, ex­cep­tions. Bowie was the pic­ture of give-a-fuck in­sou­ciance wear­ing a fe­dora dur­ing his Thin White Duke pe­riod, and Frank Si­na­tra looked great wear­ing a trilby through­out the Fifties. Even Liam Gal­lagher looked stylish, in a scary, scruffy way, wear­ing his col­lec­tion of bucket hats dur­ing the Nineties. But all these ex­am­ples are a) pro­tected by the gos­samer veil of nos­tal­gia and b) demon­strated by men so over­spilling with per­son­al­ity and charisma that each would have looked good wear­ing a tur­ban made from his grandma’s cur­tains.

Per­son­al­ity ac­ces­sories — af­fec­ta­tions de­signed to im­bue their wear­ers with char­ac­ter they don’t ac­tu­ally pos­sess — are, in short, best avoided. Jazzy pocket squares, fancy ties, jaunty hats. Un­less you are a man so con­fi­dent in his own abil­i­ties and so re­spected within his field of in­flu­ence (which I have no doubt you are, Ber­trand) that you can wear what­ever you like, when­ever you like, any­thing other than a Panama in the sum­mer or a deer­stalker in the win­ter is bet­ter off left on the hat stand.

If you are de­ter­mined to wear a hat out of sea­son, there are a few op­tions that will in­flict min­i­mal dam­age and maybe, just maybe, make you look more stylish. An ul­tra-min­i­mal wool or cash­mere base­ball cap in a neu­tral shade of navy, black or char­coal can be a taste­ful way to cover up an early on­set bald patch. This style of hat can look sur­pris­ingly good worn with tai­lor­ing in a com­ple­men­tary shade. Whis­tles does a nice line in these, as does Cos. Lock & Co also has a great range of en­gi­neer’s hats. There are light linen ver­sions for warmer days and there’s a great cash­mere op­tion for when the tem­per­a­ture drops. If you’re bald, a good mild weather choice can be a merino wool bur­glar beanie, de­signed to sit high on the head

(never slouched down to the nape of the neck). Ami does a fine se­lec­tion of these. Just be sure to wear one with more ca­sual out­fits: bean­ies and suits do not mix.

And as for your comb-over, Ber­trand. Cut it off. For the love of God, cut it off.

Black wool-cash­mere train driver cap, £200, by Lock & Co Hat­ters; lock­hat­

Grey wool cap, £50, by Whis­tles; whis­

Red wool beanie hat, £70 by Ami; ami­

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