Unpacking the perfect holiday shirt

Unpacking the perfect holiday shirt

For some reason, and only partly to do with a change in climate, when we go away on holiday to sunnier climes, we suddenly find ourselves compelled to buy resort clothing that we wouldn’t ordinarily wear at home. Yes, we’re looking at you garish Hawaiian shirt, and you, oddly sheer polo shirt. Maybe it’s because we think we’ll look good in literally anything when our melanin levels are topped up, or perhaps it’s more an expression of freedom, reinforced by the knowledge that nobody we know is going to see us, so why not?!

What is irrefutable is that the ‘holiday shirt’ is the garment around which all your other clothes should pivot. It needs to be at all times casual and comfortable yet smart and presentable; structured and classy yet soft and louche. Sound like an enigma? It needn’t be. A great holiday shirt can be all things to all men, and slots right into virtually every conceivable look, from easy beach throw-over with shorts to a tailored approach for sundown negronis at the swanky spot.


There is certainly a time and a place for the floral print, Hawaiian style ‘look-at-me’ shirt, but it’s not now and it’s not this article. No, we’re seeking out that more refined and versatile shirt that’s at home in Santorini, St Tropez, or Lake Como - the style that doesn’t need to shout to get noticed. I suppose what we’re trying to express here is the very essence of the Italian word ‘sprezzatura’ that first appears in Baldassare Castiglione's 1528 The Book of the Courtier, where it is defined as "a certain nonchalance, so as to conceal all art and make whatever one does or says appear to be without effort and almost without any thought about it.”

Anyone who has visited Italy in August will know that the Italians have sprezzatura down pat, whereas us northern hemisphere wildlings sometimes struggle to acclimatise our holiday wardrobes. In short, we try too hard. We are sometimes prone to distilling all of our fantasies about the Mediterranean summer into our clothes, whereas in actual fact, all we need is a simple button-down Oxford shirt, or a nicely cut seersucker short-sleeved shirt to look like the polished local, rather than the over-eager tourist. So where do we start? Below we breakdown the essential holiday shirt styles and offer some cinematic references for inspiration…


The Oxford Shirt

Oxford shirt for holidays


The classic Oxford shirt is non-negotiable. A button-down collar is a nod to the original polo style and gives it a sportier edge but you can go for a soft-rolled spread collar or the rounded Eton collar for equal effect. A lightweight cotton with a nice handle is a great versatile fabric, while linen is brilliant for those hot days at the beach or around the pool. The shirt structure and collar are all the formality you need, while the lightweight, breezy fabric brings the casual vibe in spades. Styling-wise, keeping your colour palette neutral is a fail-safe option that will allow you to pair the shirt with all manner of shorts and summer trousers. Add a roll-up in the sleeve for a little Mediterranean insouciance or be a bit more regimented with a carefully folded sleeve that finishes above the elbow.

Wear it with: Classic cotton shorts in a neutral tone with a pair of Quoddy's Bluchers for a chic fit during the day, then swap out the shorts with a pair of pleated trousers for the evening, or dress it down slightly with some judo trousers. Accessorise with Bleue Burnham's jewellery.

Big screen inspiration: American Gigolo, Plein Soleil, A Bigger Splash, The Thomas Crown Affair.


The Camp-Collar Shirt


The Long-sleeved vs short-sleeved is not even a debate. Take both. The latter can come in a variety of cuts, from boxy bowling shirt to a slightly more fitted camp-collar Cuban style, but we’d avoid going for overly loud prints. Let the silhouette and fabric do all the talking. The camp collar is a great style for during the day and can easily be worn with shorts for a beach look, but it also comes into its own in the evening. Its standout feature is a sort of mini lapel, reminiscent of the style worn by 18th-century South American farmworkers. It became especially popular from the 50s onwards, when Cuban immigrants introduced it to American shores. The style lends itself well to pleated trousers and loafers for a smarter fit.

Wear it with: Think laidback and carefree when it comes to the camp collar shirt. Neutral tones will keep the focus on the collar details so stick to a tight colour palette. Cotton shorts are a great option for during the day. For the evening, layer with a linen jacket for a casually tailored look with a sprezzatura vibe.

Big screen inspiration: La La Land, Thunderball, Goodfellas, Do The Right Thing


The Short-Sleeved Shirt


Camp collars and bowling shirts aside, having a stellar short-sleeved shirt in your holiday kit is a great idea since it’s very easy to throw on with some shorts for that smarter lunch or early evening negroni. Your moodboard comes courtesy of Sean Connery as James Bond in the 1975 flick Thunderball, where he wears not one but five different styles with a combination of swim shorts and tailored chinos. You want to avoid overly fitted short-sleeved shirts as they’re not particularly flattering - that’s why we cut our styles with a more relaxed silhouette that can be dressed up or down as necessary. Seersucker is a great fabric option since the dimples in the fabric create air pockets to help keep you cool. The natural crumple also minimises the need to put that dodgy hotel iron to use.

Wear it with: While the short-sleeved shirt is perfectly slick with shorts, we think it's ripe for some smarter 50s styling, so opt for a pair of pleat trousers cut slightly higher on the waist. Sneakers will add a sporty finish to the look but for a little more polish, we'd recommend stepping into some of Paraboot's latest loafers.

Big screen inspiration: Thunderball, Call Me By Your Name, The Talented Mr. Ripley





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