Depending on what one does for work, most of us live day-in, day-out in the same clothes, and frankly, it can get a little boring.  Even if one adds items for social occasions, sport, and loungewear, unless one is looking to draw attention to oneself, you’re generally limited to what is practical and acceptable for whatever society you live in.  But traveling, especially to another country and culture, opens up opportunities to do as the Romans do in an environment and setting free from dress codes or OSHA requirements.  Why not take advantage of it?

If old Esquire articles are any indication, resort wear was practically born on vacation, simultaneously in the Riviera, the Far East, Africa, the Caribbean, and Brazil – everywhere that Americans and Brits would go on holiday.  Once away from home, travelers were free to incorporate local dress in a manner that would otherwise be considered outlandish and were encouraged to do so liberally; bold prints and vivid colors might be garish in the boardroom, but they fit in perfectly well amongst the tropical flora and fauna.  Rough-textured and wrinkled fabrics might not inspire confidence when meeting clients downtown, but in 100 degree weather and 100% humidity you’d be mad to consider anything else.   Sandals, espadrilles, and loafers were the preferred footwear, because who wants to be troubled with laces on vacation?

In such an environment, a suit almost seemed silly, but for occasions that did require it, suiting options were white, tan, peach, yellow; anything but dark worsted.  Since most of one’s vacation time would be spent in less formal settings, the majority of the suggested outfits offered were much more casual, and some were fairly avant garde, especially given the time: a Mexican poncho in terry cloth, a diaphanous shirt in silk mesh, a pith helmet, and matching beach-jacket-and-shorts combo in madras.  Loose fits, open weaves, and indigenous motifs were choice favorites.

How well-heeled socialites of the time would become willing – if only on holiday – to trade bow ties for bush shirts is a mystery.  Or did they secretly love sarongs all along?  Who knows, but many items that were introduced as “resort wear” eventually made their way from the elite to the masses.  The jippi-jappa hat, for example, was a straw hat typically worn by plantation laborers in Jamaica and adopted by vacationers in Nassau.  The happi coat was a westernized version of the Japanese hanten shirt, described as a “short sleeved, sawed off kimono”; originally worn by summertime workers in the field, its loose, belted fit and open sleeves offered breezy comfort with just the right amount of international panache when lazing about under the umbrella.

Some of these looks were reinterpreted in the 90s, but in contrast with the heavy and dry cloths of the past, new weaves lightened up the fabrics and gave them a drapey, luxe feel.  roomy trousers, easy-fitting band collar shirts, and softly constructed and unlined jackets in various shades of white or muted hues of earthy colors are perfect for leisure pursuits among the sandstone and faded whitewash of the Mediterranean.  Say what you will about “fit”, but there’s nothing that’ll kill your chill quicker than constricting clothes.

In fact, many designers have been resurrecting this louche look for the last few years in their collections.  My favorites for summer resort-hopping are the ones that capture a hint of that vacation vibe without going overboard. 

If you’re just dipping your toes into vacation wear, stick with the basics – shirts, trousers, and shoes – and choose casual fabrics in light or summery colors.  Look for telltale signs of do-nothingness: rayon camp shirts with collars meant to be worn open, drawstring linen easy pants that accommodate overindulgence, and slip-on espadrilles. 

You don’t have to go all-out baggy everything; an easy way to incorporate loose fits is by playing with proportions: roomy trousers with a more fitted top, or a slightly oversized shirt with classic-fitting shorts. 

Much inspiration can be taken from Antonio Ciongoli’s tenure when he was the creative lead of Eidos.  During my last few vacations near the sand and sea of Sicily, I found myself constantly reaching for his gauzy, wide-legged trousers and loosely belted jackets in breezy, textured fabrics.

I love Charlie’s wardrobe choices (@sebastianmcfox on StyleForum and Instagram) from when he was in Italy this summer.  For dressier occasions under the Tuscan sun he wore a nubby linen green jacket, white polo shirt, tan Panama hat, khaki cotton trousers and brown loafers.  For a wedding he wore a tobacco linen suit, tasteful light blue shirt, black grenadine tie, and white pocket square.  His more casual outfits consisted of just one print, usually a camp collar shirt or striped tee, and safari jackets in linen and cotton, easy pants, and white sneakers.  Everything looks comfortable, relaxed, and stylish.  In other words: perfect vacation wear.

For someone who enjoys clothes, you can’t do much better than a vacation as an excuse to expand your wardrobe.  Or at the very least, attempt to.  Not only will you look cool, you’ll wear cool as well, and besides, it’s great fun.  Embrace the batik.

Pics from Esquire, Urban Composition, and Sebastian McFox.

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Peter Zottolo

Peter works in construction, but has an extensive collection of custom suits which he gets so that he can wear suits on the weekend. Even though he lives in San Francisco, he has never used the word "impact" as a verb. He writes about classic menswear and is one fedora away from being a complete dork.

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