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 inThe Big
Sleepand Delon inLe
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 inNow 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 inThe Two Faces of Januarypairs 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 showPeaky
Blindersreturning 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 inThe
Avengerscombine 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).