If there’s a divisive, unruly wild card in men’s fashion, surely the Hawaiian shirt is the main contender.
Riotously noisy and as vivid as house party of flamingos, the Hawaiian shirt and its ilk are soaked in polar stereotypes thanks to Hollywood. There’s the original retro loverboy Elvis in Blue Hawaii. Or the equally lovable, yet woefully uncool, all-American buffoon: think the late great John Candy in numerous movies. Leo and Brad both nailed the look with smouldering chutzpah in Romeo + Juliet and Once Upon a Time… in Hollywood. It’s even the unhinged lunatic’s outfit of choice: check De Niro in Cape Fear and Pacino in Scarface.
Aficionados (yes, they exist) are still debating the precise origins of the Hawaiian shirt, but two duelling stories take centre stage. The first claim is made for Ellery J Chun, the son of Chinese immigrants, who began selling shirts cut from Japanese kimono fabric at his Honolulu store in 1931 after noticing the brightly coloured clothing worn by local Filipino and Japanese boys. Chun registered the “Aloha” trade name 1n 1936, which Hawaiian shirts are still known as today. This was rather inconvenient for historians as a year previously another local tailor, Koichiro Miyamoto, had taken out an ad in the Honolulu Advertiser for “aloha” shirts.
Arguments aside, it was less than a decade before American GIs and wealthy tourists began returning to the US draped in Hawaiian shirts, thus imbuing them with kudos and aspiration. The aloha shirt has gleefully never looked back since.
Beauty is in the eye of the beholder and this phrase is never more tested than with a Hawaiian shirt. One man’s edgy aloha look for cocktails and sushi at Nobu Malibu is undoubtedly going to be another man’s day-glo dog’s dinner.
So we’ve put together an edit that covers all the bases, from “I’ve just come back from the best ever holiday in Maui” shirts to some subtler, less typical takes on the trend.
Scotch & Soda Printed Hawaiian shirt
Best for: attention to all the delicious details
Whatever wardrobe item you’re hankering after for the new season, keep Amsterdam’s Scotch & Soda on speed dial. They always deliver the goods with something a bit special.
Right now, we want to look like the hippest cat in the Pacific and this cotton shirt does just that, but with extra touches of class. It’s got a punchy flowers-and-guitars motif, but instead of being an all-over print, this one elegantly wraps around the sleeves and across the bottom of the back. There are lovely buttons too, each one a different colour. The collar is spread lazily wide, while the sleeves are crisply turned over.
See, it’s all about the little details and we love them all. And don’t worry if you haven’t a smokin’ beach party to go to, this will bring joy to any place you wear it.
Buy now £115.00, Scotch & Soda
Desmond & Dempsey Cuban Pyjama shirt
Best for: the bed and BBQ multitasker
Yes, you read that correctly, it does say “pyjama”. Because if Desmond & Dempsey is known for one thing, it’ll be its super stylish sleepwear.
Here however, the brand is taking PJs outdoor with an eye-popping tiger print. Cut in a loose, boxy shape in lightweight cotton, this is intended for both the bedroom and the bar room. We love the retro vibe of sun-streaked Sixties Havana streets, and that big cat is much more charmingly cute than scarily menacing.
If you want to go the full monty, there’s matching shorts or trousers too. This isn’t just the tiger that came to tea - it took you out to the pub and tucked you up in bed, too.
Buy now £80.00, Mr Porter
AllSaints Florax Floral shirt
Best for: laid-back, lazy days
Cut from a lightweight and sustainable viscose mix in a relaxed fit, this blurred floral print in vibrant minty green, pink and yellow from All Saints is a standout addition to any summer casual kit.
Pearly buttons and camp collar add to an overall feel that’s breezy, bright and brilliant for the hazy sun-kissed days ahead of us (they will come).
Pair with All Saints beach shorts or linen chinos for the ultimate laid-back look. The left chest pocket is the essential finishing touch - just clip your sunglasses over the top button and you may as well be on holiday.
Buy now £95.00, AllSaints
Paul Smith Yellow ‘Stem Floral’ short-sleeve shirt
Best for: a proper (British) Italian job
As ever, the quintessential Paul Smith offers nothing but quality and attention to detail with this yellow ‘stem floral’ pattern shirt. It oozes Italian style combined with PS’s classic British touch of class with its camp collar with loop-button fastening that sits relaxed on your skin and shell button placket. Made with viscose, and in a more tailored fit than other Hawaiian shirts, you’ll feel like the don at any summer barbecue or beach party. Pair with linen trousers or chino tapered shorts for the perfect look.
Buy now £275.00, Paul Smith
Reiss Yung Cuban shirt
Best for: big leaf energy
You can always rely on Reiss for a contemporary twist on a classic style and their take on the Hawaiian shirt is no exception.
This is a summer wardrobe must-have with its relaxed Cuban collar that insists on being worn without the top button done up to give you that summer vibes look and to maximise airflow - keeping you not only looking cool, but your body temperature regulated. This isn’t a shirt to barbecue in; it’s a shirt to stand around in chilling with an ice-cold bottle of beer watching your pal labour away on the grill while you stand back and soak in the sun.
The regular-fit cut effortlessly drapes over your torso and with its bold leaf pattern printed around the shirt in a layered duotone design, you’ll be bringing your casual A-game into the summer months.
What’s more, it’s made with recycled polyester yarn, another Reiss initiative to make their garments more sustainable. Available in green or pink duotones.
Buy now £88.00, Reiss
River Island Red Floral shirt
Best for: affordable high street chic
Sometimes you don’t need to break the bank to bag the best – just having a brilliant eye can get you the prize. And we’re sure we’ve spotted a cut-price gem here. The proof? Wearing this out, we got more positive comments (actual IRL likes!) than any of the shirts on this list.
Some people who should know better even speculated that it was from brands at ten times the cost. The abstract black and navy foral print on deep poppy red says you are a man who walks his own way - this isn’t a shirt for sheep. And being viscose, it hangs softly and nonchalantly too.
Where to wear it? Anywhere. When to wear it? It’s an everyday winner.
Buy now £30.00, River Island
Aloha Republic Hawaiian Sunset shirt
Best for: the genuine island spirit
Let’s be brave and dive right in with the full “aloha”. This is most certainly the genuine article, made by Aloha Republic in Honolulu and featuring a quintessentially Hawaiian print. Loud and proud shirts are a joy when done well like this one –that print reminds us of those sublime tropical sunsets from holidays past.
This is a light cotton poplin fabric that’s made for scorching hot days (and nights), and for even more bona fide cred, the buttons are coconut shell, a detail on which some purists insist. But can you wear this when you’re not on Waikiki Beach, you ask? All we can say is that it seemed to blend in rather well on a Saturday-night bar crawl around east London.
Buy now £44.99, Hawaiian Shirt Shop
Magic Castles Waves Print Gold shirt
Best for: a musical trip
Drop the needle on your favourite record and bliss out in this slouchiest of future retro numbers.
The wave print is a gently psychedelic nod to Hawaiian beachscapes by artist Kate Gibb, better known for her work with the Chemical Brothers, notably their iconic Surrender album cover.
Cut from floppy rayon, this hangs lazily off the shoulders – check yourself in the mirror and the words “I’m The Man” might spring to mind. Corozo nut buttons add a twist to the traditional aloha coconut ones.
Want the perfect tunes to accompany this beauty? Magic Castles do that sublimely too: dial into their Soundcloud or one of their Soho Radio shows while mixing your Mojitos.
Buy now £160.00, Magic Castles
Far Afield Stachio shirt
Best for: florals with finesse
Just like attempting to slide into your beach hammock after your fourth piña colada, nailing the florals game can be a tricky business. Too many brash colours and you’ll risk looking like Laura Ashley on acid; play it too safe and you’re walking around in granny’s tea towel.
Far Afield’s gorgeous Amazonian lily print is your best friend here: it’s unusual, delicate and totally sidesteps the Hawaiian clichés. Crafted from planet-friendly Tencel (a greener form of viscose), this relaxed shirt is another that drapes off the body wonderfully.
And don’t pack it away once you’ve worn it to death on holiday – we discovered it goes rather brilliantly under a dark suit jacket with black jeans.
Buy now £90.00, Far Afield
Ning Traditional Silk shirt
Best for: modern Chinese hyper-luxury
A Chinese man in Honolulu was responsible for the first Hawaiian shirts, and now almost a century later there’s a Chinese woman in London making incredible printed clothing.
Self-confessed hypebeast Ning Yuan boldly launched Ning in 2021 at the height of Covid and the label – which has already shown at London Fashion Week – oozes desirability. Taking its design cues from international streetwear, ancient Chinese heritage (plus a heady dose of the country’s modern hedonism), the prints are eye-poppingly exquisite.
Beyond the moreish imagery, it’s Ning’s chosen fabric that takes this up a level: luxurious mulberry silk, made by the only producer bearing the Forbidden Palace seal, no less. And if you’re believing the hype, there are some even more wildly delicious pre-order shirt designs dropping as we type…
Buy now £430.00, Ning Dynasty
RJC Hawai’i Tiki Room shirt
Best for: the full-on holiday vibe
Go all-in with something that shamelessly screams, “I’ve been to Hawaii”. And if you don’t like a touch of kitsch, shame on you.
We’re obsessed with this print that plays on the interior style of a typical tiki bar room and the tourist clichés of the islands. It’s not shy, and neither are you when you’re wearing it.
This shirt is another that’s made in Hawaii, this time from a brand founded in 1953 by a former US serviceman, so it’s crafted from lightweight cotton poplin and has those oh-so-crucial coconut buttons. If you find yourself leaning towards the genuine thing (and at very reasonable prices, too), the Hawaiian Shirt Shop should always be your first port of call.
Buy now £49.99, Hawaiian Shirt Shop
Aries Glycon Hawaiian shirt
Best for: cult fashion lovers
Like a select band of streetwear labels, Aries is almost a religion for its devoted fans, so what better to be slithering over this shirt than a second-century snake god. Glycon had quite the following 2,000 years ago and suits this psychedelic print perfectly.
Of course, because it’s Aries you won’t look like a mushroom-addled Sixties casualty in this – think more 21st century edgelord. It takes some talent to blend tie-dye neon orange and a mythic reptile to such brilliant effect. Like many of our faves here, this is cut from a soft and loose fabric (this time rayon) for that louche, laid-back feel.
And don’t think this one’s just for summer days – pop it under a dark, plain suit and it looks even better.
Buy now £210.00, Aries Arise