How To Wear A Hawaiian Shirt Without Looking Like Your Dad On Holiday

Not even a whiff of naffness

How To Wear A Hawaiian Shirt Without Looking Like An Embarrassing Dad

by Natalie Hammond |
Published on

Let’s be frank – Hawaiian shirts have long been seen as the uniform of dads abroad. Much worse than socks with sandals (at least men with Velcro-fastened footwear don’t class themselves as ‘hip’), more offensive than combat trousers (even the type where you can zip the legs off to air the calves), and heinous in comparison to an ‘invisible’ money pouch that you stuff down said combat trousers. Or are they?

Take Leonardo DiCaprio in Romeo & Juliet. A story of woe it might be, but even the Capulets couldn’t deny that the dashing young Montague in that Hawaiian number was something of a sartorial pioneer. Then there’s Winston Bishop, my favourite character on New Girl, who loves a Hawaiian shirt almost as much as his cat Ferguson. Moving swiftly on to French model Constance Jablonski, who recently Instagrammed herself in none other than a Hawaiian shirt knotted at the waist. Naturally, it looked Magnifique.

Lest you think this is a look exclusively for supermodels and star-crossed lovers, you should know that the high street has plenty of tempting options. Mango has three short-sleeved shirts that come embroidered with banana leaves, printed with striped parasols and generally look like St Barts on a blouse, while H&M has a style that will give pause to the most truculent Tiki-shirt-haters. It’s silky for starters, and looks more like a pyjama top printed with a scene from Moana than anything you’d find on board a cruise ship.

Still not sold? These five ways to style out Hawaiian shirts might just convince you.

1. With equally loud trousers


Perhaps not one for the office – you might find yourself grimacing after the 10th person quips, ‘still in pyjamas, are we?’ – but you’d be surprised how a pair of loudly printed trousers can take the edge off a Hawaiian shirt. This shell-pink one from Mango is an upgrade from your traditional palm tree prints, and doesn’t have a hint of Jim Carrey in Ace Ventura: Pet Detective about it.

2. As a jacket substitute

It’s a truth universally acknowledged that us Brits will spend summer looking like a sheepish pack of lobsters. One idea is to cover whatever skimpy piece of cotton you’re calling a “dress” with your Hawaiian shirt. If you can bear it, I’d suggest something that reaches the mid-calf like this textured dress from Nanushka that, now you mention it, looks rather like a grass skirt.

3. With dungarees

People are wary of dungarees, and they are excessively annoying if you have a small bladder, but somehow they make a Hawaiian shirt look cool in an un-ironic way. Avoid wearing with flip-flips unless you want people to ask you where you’ve stashed your surf board. Something smart like gold loafers or Converse trainers will soon shut them up.

4. With a matchy-matchy skirt

I bought this shirt for a tenner at a vintage market stall and have been waiting about a year to find something it goes with. Enter this sunny-side-up skirt from Sea that brings out the primrose-yellow on my shirt a treat and, hopefully, makes it look like less of a printed sack. Whatever yours is patterned with – hibiscus, conch shells, a friendly turtle or two – pick a similar colour and it’ll make it pop.

5. As a beach cover-up

This is sailing dangerously close to Tom Selleck in Magnum P.I., but at least it’s something different to the type of wafty kaftans that make people ask if you’re expecting. Tying it to reveal a hint of tummy – note how high my skirt is pulled up to conceal as much pale skin as possible – is a tip from straight from Constance Jablonski so blame her if it backfires.

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Follow Natalie on Instagram @nataliehammond

This article originally appeared on The Debrief.

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