Let’s hear it for the Ostentatious Winter Hat

Photo: Getty Images 

From baker boy hats to embellished berets and her Terry Pratchett fedora, Lauren Bravo makes the case for attention grabbing headwear that is, actually, more practical than you might think

Added on

By Lauren Bravo on

I hope you won’t immediately hate me when I tell you that I’m a hat person. I am, I can’t deny it. To be fair, I believe fate has blessed me in this area to make up for not being a jeans person or a jumper person, or a shirt person, or a maxi person or a shift dress person or a T-shirt person, but still – it’s a precious gift.

I can measure out my life in ostentatious hats (or “OHs”, which is the noise people tend to make when you appear in one). There was the velvet bucket hat with the turned-up brim. A cord baker boy hat, which looked like something Fagin’s gang might stash silk hankies in. The tweed flat cap I bought jointly with a friend and wore in shifts, in misguided homage to Madonna's landed gentry phase. The black felt fedora that got dubbed my “Terry Pratchett hat” within five minutes of purchase. The peaked black riding cap that I wore confidently all of winter 2012 because Vogue said equestrian style was going to be huge (it wasn't), and the hand-knitted beanie with a bobble so big it gave me neck ache. I even secretly loved my school hat, which was bright red with a Latin motto on it, which was visible if tipped at a rakish enough angle.  

Wear a hat and you’ll usually be remembered. Not always for good reasons, especially if you’re That Person blocking their view, but still I believe everyone generally appreciates the visual drama. Isabella Blow, the late fashion director and Philip Treacy muse, famously wore her hats “to keep everyone away from me.” And that’s the double draw of extravagant headgear; it removes you from the world a little, while also making the world immediately more interested in whatever’s hiding beneath the brim. Like the child who thinks nobody can see them if they put their hands over their eyes, a good hat makes you feel incognito while looking anything but.  

Once the temperature drops below 10 degrees a hat isn’t just a fashion accessory, it’s a sensible health preserver. If anyone makes a wisecrack, you can sneeze on them

Look, I understand your reservations. Hats are, by their very nature, a bit extra. Unless you’re a Norwegian fisherman or a professional jockey, they’re usually surplus to requirements. They’re the thing you put on last, dither about, fuss over and often take off again because you’re worried everyone on the street will point and yell “HAT!” After all, just this weekend the internet celebrated Lenny Kravitz Scarf Day, a commemoration of the day in 2012 that Lenny Kravitz went out wearing a knitted scarf so enormous you could almost see it from space – and a cautionary tale for the bold accessoriser: not everyone will get it. As Jerry Seinfeld once noted on the ear-flap trapper hat, “This hat says to the world: ‘I would rather have the heat in my skull than anything society could possibly offer.’”

But as your friendly designated Hat Advocate (“Hatvocate”), I’m here to argue in favour of the ostentatious hat. Or at least, the Ostentatious Winter Hat. Because while summer hats have their problems, now is the perfect time to indulge. For one thing, winter offers by far the best selection of options. Hat-wearing 101 is the beanie, naturally – even the most nervous accessoriser can wear a woolly hat without much hassle. But there’s a whole parade of other options you can graduate to next. This season’s beret, for one. Winter baseball caps (they’re a thing now). Cloche hats, for all your latent Bugsy Malone fantasies. Floppy brims or felt boaters, eccentric knotted turbans and the final frontier: giant furry Doctor Zhivago affairs. Whack any of them on and instantly look like you’ve made 300 per cent more effort.

And for another thing, it’s cold. Once the temperature drops below 10 degrees a hat isn’t just a fashion accessory, it’s a sensible health preserver. If anyone makes a wisecrack, you can sneeze on them.

But the most important decision you’ll face with the OWH is where you want to sit on the Venn diagram of winter fashion choices. You know the one I mean – there is a circle marked “Warmth” and another marked “Style kudos” and every time we put on an outfit between November and March, we’re unconsciously choosing a place on that overlap. One day we might prioritise the warmth, the next we might veer towards the style. Sometimes we fall out of one circle entirely, as with last Wednesday when I went out in bare legs and suede trainers and suffered the consequences. So choose an OWH that covers at least half your cranium and stays on in a breeze; you’ll be much less likely to end up hurling it into a hedgerow.

And if it all still feels a bit much, a bit too Kravitz, try taking your scarf off to pare things back. But I beg you, don’t bow to peer pressure. Leave your hat on.

Click here for the best winter hats on the high street


Sign up

Love this? Sign up to receive our Today in 3 email, delivering the latest stories straight to your inbox every morning, plus all The Pool has to offer. You can manage your email subscription preferences at My Profile at any time

Photo: Getty Images 
Tagged in:
fashion honestly
fashion advice
Wardrobe Stories

Tap below to add
the-pool.com to your homescreen

Love The Pool? Support us and sign up to get your favourite stories straight to your inbox