Yes, you can look stylish in a woolly hat

Every time there’s a cold snap I find myself wrestling with the same problem: how to keep my head warm without looking like a wally.  

Because woolly hats of all kinds look terrible on me. I’ve never mastered the art of being cool in a beanie. Fine-knit styles cling to my head like a swimming cap. Chunky hats swamp my short hair and make me look bald. And anything with a pom-pom makes me feel about five years old.

Every winter I tell myself this year I’ll find that perfect cashmere investment piece. Then I give it no further thought until the mercury hits zero degrees, and I panic-buy something, anything, just to save my frozen ears.

A fleecy Poundstretcher hat is fine for walking the dog — but I’m in dire need of something more chic. And Zoë Hennessey, an LA-based stylist who’s worked on campaigns for Goop and Loewe, says there is no escaping the beanie this season.

“Céline, Etro and Jil Sander, to name a few, all showed their take on beanies in their 2024 shows. What was once styled with Dickies and Vans can now be seen in any type of look, even atop an evening gown . . . I particularly love how Jil Sander used beanies for spring/summer 2024 complementing bare arms and garments crafted from lightweight cotton and silk fabrics. The beanie is definitely about more than keeping one’s head warm!”

The beanie’s resurgence, she says, has its roots in “the pandemic’s athleisure trend, [that’s] now merging into ‘gorpcore’, or more hiking style clothes worn as streetwear”. Even if you’re not headed up a mountain, in other words, you might want to accessorise like you are.

Some of the masters of this new-wave “technical knitwear” are — no surprise — the Scandi brands: Arket (Sweden), Ganni (Denmark), Cos (Sweden) and Acne Studios (Sweden) are names uttered a lot by those who know their way around woolly hats.

But there are currently lots of styles to play with, says Sarah Cartwright, accessories buying manager at Selfridges: “Protective at Rick Owens, crafty at Loewe, chic at Toteme and bold at Burberry — the beanie has become something of a style signifier in its own right. It’s an easy way to add colour, texture or detailing.”

But how to style it successfully? “If you have shorter hair,” advises Hennessey, “try pulling some of your locks forward so they stick out of the beanie and frame your face. Wearing larger earrings that poke out can also help.” I try both and see a big improvement straight away. Several stylists recommend playing around with the width of the “cuff” or brim; a centimetre or two can be all that stands between frumpy and flattering.

Texture is also something to consider, says “headgear obsessive” and freelance stylist Flora Macdonald Johnston (formerly of the FT style desk). “Texture is what I’m drawn to, before style or shape — is it a beautiful ribbed heavy wool; is it a cool cashmere? It’s a tactile thing. But there are so many styles there’s really no substitute for just trying lots on — it’s like buying a pair of jeans.”

Head of womenswear at Matchesfashion, Liane Wiggins, advises investing in “key tonal colours: camel, black, ivory, navy or olive green . . . I personally feel solid colour versions are the best investment but a navy and cream stripe can look super chic.” She picks out the natty striped wool beanies by Stockholm label Toteme.

Heavily textured beanies with a slight slouch and a generous cuff do the best job of framing my face

My resolve to get something sensible in navy, grey or black falters when I discover the range by Le Bonnet, which comes in a rainbow of hues, spun in sustainable Scottish lamb's wool and a trio of different shapes (£60, lebonnet.com). Alas, like many beanies, I find them unforgivingly tight — despite having, according to Google, a pretty average-sized head.

My square jaw doesn’t suit the masculine, navy Mechanic’s Hat by utilitarian label Labour & Wait (£60, labourandwait.co.uk); but equally I’m not fashion-forward enough to pull off the kind of high-crowned beanies that dome like a soufflé.

After much trial and error, I deduce that heavily textured beanies with a slight slouch and a generous cuff do the best job of framing my face, especially when tipped back just above the hairline, creating a sort of halo effect.

This is hard to achieve, I discover, with the beanies from Acne Studios — considered by many to be the ne plus ultra of knitted headwear. The thick, heavy rib is very springy — so the hat does a good job of keeping its shape (£140, acnestudios.com). But it also makes it feel like it’s permanently about to pop off my head. (And I don’t like the smiley face logo on the brim, even if it is a secret handshake.)

At Arket I find similar “technical” styles for less than half the price — but it’s the deliciously fuzzy £47 mohair-blend beanies, available in black, grey and brown, that really catch my eye.

The retro ski-hat is now on-trend — and Macdonald Johnston is a fan: “I love it when a bobble is worn in a slightly more ironic way — there’s something quite fun about wearing it with your smartest trenchcoat in central London. You’ve got to play up to it.”

Buoyed by her enthusiasm, I try the graphic wool beanie by hipster favourite, Ganni — a bobble hat that looks like it could have been worn by someone from the royal family on the ski slopes circa 1983 (£125, ganni.com). Its loud Fair Isle knit in cobalt blue and pink is very jolly, but the hat feels tight and a little bit itchy — so it goes back on the shelf (but not before I’ve taken a selfie).

The understated, biscuit-coloured felted wool bobble hat by British designer Margaret Howell is more my cup of tea — if I had a daintier head, and spent my days ice skating and drinking hot chocolate, I’d probably buy one of these (£35 on sale, margarethowell.com).

My beanie breakthrough comes when I try Guest in Residence — the cashmere label by American model and serial beanie-wearer Gigi Hadid. As soon as I touch the richly coloured, wonderfully soft designs I can’t wait to get them on my head. It’s the slate-grey Rib Hat, with its relaxed fit, busy texture and wide cuff, that’s the one for me. It’s roomier than average on the crown but still has sufficient grip around the ears. It feels stylish but also — as you’d hope for £160 — it feels like it won’t date. Within hours of trying the grey one, I’ve bought a tomato-red one in the sale.

What knitwear can I conquer next? I note the balaclava is also back in vogue at Guest in Residence and The Row. But it will have to get really, really cold before you catch me in one of those.

Find out about our latest stories first — follow @financialtimesfashion on Instagram — and subscribe to our podcast Life and Art wherever you listen