In search of the perfectly packable holiday hat

A mental image of the woman I will become on holiday resurfaces every summer. This woman is never flustered or stressed in the face of flight delays. She packs an assortment of linen dresses — miraculously never creased — and a single pair of sandals into a carry-on suitcase that never threatens to burst. Her swimwear is unmarred by sun-cream stains from holidays past. And she is always, always equipped with a fabulous hat.

I don’t mean a bucket hat. I mean the kind of hat with a sweeping brim that can transform any poolside situation into a Slim Aarons scene. The right summer hat offers shade and sun protection, sure; it also invokes Sophia Loren in Venice, Jeanne Moreau in St Tropez and Ingrid Morath in Acapulco, all rolled together.

That is, if it reaches its destination unmarred. Just as there’s more than one impediment to realising the me-on-holiday ideal (hello children, hello easyJet), there are several to being a Summer Hat Person. The main obstacle is practical: the hat I have in mind seems impossible to pack without incurring damage. When I’ve packed a big hat, it has reached the beach in less-than-pristine condition — not necessarily cracked, but bent out of shape or otherwise wonky, in an unpinpointable but irremediable way.

How do people do it? In Antigua last December, I peered up from under my visor (crumpled, obviously) to spot a woman dipping her feet in the sea wearing the dream hat: wide-brimmed straw with a striped ribbon. The next day, she wore a different design in black raffia. I complimented her and asked if she could share her methods. She smiled. “I take a hat box as hand luggage,” she said. Three cheers for commitment, but . . . hat boxes? Really?

“The trick is to fill the crown of the hat with your undies, and then make a little well in your other clothes and put it in your suitcase,” says Jess Collett, the London-based milliner who created the headdresses worn by Catherine, Princess of Wales and Princess Charlotte at the coronation of King Charles III in May. Her bestselling design is her World Traveller, a panama hat made in a malleable polyester-cotton ‘straw’ (£225, jesscollettmilliner.com).

“I don’t recommend folding it for long periods, but if you’re out and about, you can pop it in your bag, and then it springs back into shape,” Collet says of her packable trilby. “You can even iron the brim.”

Suitcase volume is precious, so hats designed with packability in mind can be sanity- as well as space-saving. The best of these include Rae Feather’s Jane (£70, raefeather.com), which arrives pre-rolled, and Janessa Leoné’s Rhett hat ($267, janessaleone.com), which has a wire in the brim to facilitate reshaping after inevitable suitcase-related injuries — hat-tip to stylist Becky Malinsky for this discovery.

If you aren’t as bucket hat-averse as I am, consider Miu Miu’s crocheted bucket hat, the Instagram-bait piece of the season (£860, mytheresa.com). Tory Burch’s floral crocheted design (£290, toryburch.com) and Lucy Williams’s striped raffia bucket hat for Ancient Greek Sandals are less-recognisable alternatives (£155, ancient-greek-sandals.com), and Toteme’s faux-raffia bucket hat offers a sleeker take on the trend (£220, matchesfashion.com). Simon Porte Jacquemus, the French designer who ushered in the 2018 obsession with two-foot brims, now offers some surprisingly practical styles. Like a beige wide-brim hat with no branding and rear tie fastening (£68 on sale, brownsfashion.com).

For men as well as women, a classic panama — but rollable — from Lock & Co will never look out of place. The rise of the fashion baseball cap is also a boon — logo styles abound, or plain hats from Octobre Editions, Stiksen or Arket are lower-key and highly packable. Visors are another oft-overlooked option. Along with Collett’s favourite rollable styles, you might try Pucci’s printed silk-twill visor, with its scarf-style ties (£159 on sale, matchesfashion.com), or Erdem’s floral-print linen-trim raffia visor (£315, net-a-porter.com).

“The right hat can finish an outfit off like a beautiful pair of shoes,” says Sydney-based designer Lorna Murray. “Yes, it’s practical because it gives sun protection, but it’s also just a beautiful statement-maker. It gives you that refined, polished look.”

Murray’s pleated lampshade hats (from £88, lornamurray.com.au) are instantly recognisable from the Amalfi Coast to Singapore (she’s sold 40,000 since introducing them a decade ago). The beauty is that the hats pack down to the size of a packable rain jacket, as Murray demonstrates with a flip of the brim and a deft fold. “I squish them down among my swimmers and shirts and dresses, just like that,” she says. “They hold beautifully and are really elegant and structured.”

Sometimes, though, drama is required. Then you’re going to have to choose the kind of hat that takes up space without conceding to convenience. Styles worth the hassle include the beribboned Michelle and floppy Delphine hats from Maison N.H Paris (€195 and €120, maisonnhparis.com), Eliurpi’s vintage-look Pamela (£476, harrods.com) and Sensi Studio’s open-weave Aguacate (£205, matchesfashion.com).

Of course, you may choose to forgo packing it at all. “I just wear it on my head. I literally walk through airports and sit on planes wearing my straw hat,” says Susan Corsini, founder of travel-centric lifestyle brand Mondo Corsini. Always “a big hat woman”, she invested in “the perfect wide-brim straw hat” from Australian designer Helen Kaminski about 10 years ago, and has worn it on flights to Tuscany and Corfu ever since.

“I know it sounds ridiculous. My children might find it a little bit humiliating. But if it means keeping the hat looking good, then I don’t mind. I’m not going to roll it up in my luggage and hope for the best.”

Wearing a hat on the plane is practical and space-saving. It can also make you feel like you’re cosplaying Daisy Jones in Terminal 5 at 6:30am. Between packing and wearing, there may be a third way. Last November, before a flight to Miami, I slip-knotted a hair elastic through the tag in the brim of my Eric Javits Hampton hat, and wore it around my wrist until I could tuck it into an overhead bin. Voila: the perfectly packable if unpacked hat.

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