The overriding concern when wearing a hat is that you can appear
too try-hard, effete or pretentious. To avoid this, and prevent
your accessories fighting for attention, go for a tonal palette and
if it feels like you’re going over the top, keep things minimal.
Treat your hat like your tailoring, and respect all the usual rules
when it comes to fit, proportion and personal taste. The secret is
in simplicity, so here we look to some of the most stylish
hat-headed gentlemen whose distinguished style is classic and
timeless.
1. The Fedora
A particularly nostalgic style
reminiscent of a glamorous era gone by, the more formal fedora’s
sweeping brim and tall crown evoke Bogart in The Big Sleep and Delon in Le Samouraï. Both wear theirs with a trench coat for
clandestine cool, and the extra length in their outerwear helps
balance the proportions of a wider-brimmed hat, but Morgan Freeman
ups the ante in dramatic, deep purple eveningwear and a black
fedora in Now You See
Me. The lesson here is
to keep the colour of your fedora neutral so you can get as much
wear out of it as possible, as they only get better with
use.
2. The Panama
Historically, the Panama has a
somewhat regal feel to it, favoured as it was by colonial viceroys
and royals in tropical climates. Ultimately, though, Panamas are a
worthy feat of patience, artisanal skill and craftsmanship, and can
take months to be made. Keep one in your holiday home, and return
to it year after year – these are built to last, and you can even
roll them up and pack them on your travels. Viggo Mortensen’s
character in The Two
Faces of January pairs
his with light linen tailoring and a Tag Heuer Chronograph,
although chambray shirts and beachwear work equally
well.
3. The Peaked Cap
A combination of hit show
Peaky Blinders
returning and the ever-increasing
desire for more informal dress has seen baker boys and flat caps
re-adopted in a big way. The structure and design of the peaked hat
allows for a wider variety of fabrics to be used, so the only hard
part when buying one is the endless amount of choice. Jean Paul
Belmondo, above, pairs two contrasting checks (a gingham hat and
houndstooth tie) with a softly tailored jacket and striped shirt,
but a baker boy (whose volume and size is by nature more relaxed)
wears well with off-duty knitwear or a chunky overcoat.
4. The Bowler
The Duke of Edinburgh – like the
bowler hat – is a bastion of British elegance, and he is one of the
few gentlemen in the public eye still wearing one. The romantic
notion of tipping one’s hat should not be underrated, and the
bowler presents the perfect opportunity to bring back this
long-forgotten nod of respect. Winston Churchill, Charlie Chaplin
and Patrick Macnee in The
Avengers combine theirs,
respectively, with Cuban cigars, strong facial hair and a cane for
maximum effect.
5. The Beanie
The knitted beanie is the most
casual headwear option, and since it began life as standard issue
uniform in the Navy, it is the also the cosiest. Explorer and diver
Jacques Cousteau’s iconic red beanie is one of the first to spring
to mind – the colour was initially a safety measure to stand out at
sea, but became his signature. Make the beanie your own in your
favourite colour, and take inspiration from Cousteau’s wardrobe
with denim shirts and weatherproof outerwear. Opt for super-soft
cashmere or merino, which are far less itchy than wool (and will do
less damage to your carefully coiffed ’do).
