Once reserved for the financially blessed and sold during a few select months out of the year, resort wear is now a leading subsection of the fashion industry. Blame it on the psychological release still prevailing from societies post-lockdown period, an “always on vacation” mindset for those afforded the ability to work remotely, or the fact that our planet is heating up. Realistically, all three of these factors, and more, have resulted in a year-long fascination with resort wear. With the summer months officially upon us in the northern hemisphere, this fascination has peaked across the menswear landscape.

Resort is a State of Mind

To understand the rise of resort wear, we have to look at the origins of this lightweight and comfortable apparel genre, along with the state of mind it represents. Fashion historians generally agree clothing brands began building mini-lines tailored specifically for vacation purposes in the 1920s. Wealthy families in America and Europe would often travel to warmer destinations after the winter holiday season. Just as we often do now, they used their trips as an excuse to shop for new clothes. Clothing companies responded by selling specially curated lines in January through March, made up of items that were formerly reserved for summer months. 

Leisure travel had become a flex of the wealthy in Gilded Age America and Victorian England. As boat and eventually flight technology advanced in the 1920s through the 1940s, the ability to go on vacation gradually opened up to more people – though still reserved for what we would consider “upper middle class” today.

The emergence of this new market corresponds with a rebellion against the uptight fashion rules of the nineteenth century. Lightweight vacation fabrics like linen, seersucker, and madras were cut into looser-fitting designs with more exposure. Shirts became open-collared with short sleeves, interesting patterns were introduced, and stand alone shorts became prevalent. 

Relaxed travel attire became a symbol for the global mobility afforded by wealth — and the peace of mind that came with it. Those who could afford resort wear while frequenting the beaches of South Florida and the islands of the Mediterranean saw themselves as worthy of such carefree releases from their hard-working lives. The appeal of a carefree release is the psychological underpinning that has always driven resort wear. Clothing has an almost magical ability to affect how we feel so if we dress like we are on vacation then we feel relaxed like we are on vacation. While aspirational travel uniforms remained out of reach for most people before WWII, resort wear exploded into the off-hours standard of Americans and Europeans in the post-war years.  

The Golden Age of Leisurewear

Men’s resort wear as we know it today formed during the boom years following WWII. The Great Depression and global warfare hampered travel for even the most affluent for a decade and a half. As the world rebuilt and the American economy thrived, leisure time and the money to enjoy it were at an all-time high. Fashion designers sought inspiration from the globetrotting elite of the interwar years for a new age of leisurewear. Loose fits, soft and breathable fabrics, open collars, bold patterns, and – above all – relaxed vibes defined the generation that survived an apocalypse.

Cheap new lab-grown fabrics like polyester combined with advancements in mechanized garment production to make comfortable and vibrant clothing affordable to the masses. While linen, seersucker, and madras remained the standard for the wealthy; rayon, polyester, and cotton terry cloth became the resort fabrics of the people. The general idea was clothing made to be worn while sipping fruity cocktails on a beach or by a pool. Comfort was paramount but making an irreverent exclamation through dress was certainly a goal. It was an entire generation letting out a sartorial exhale. 

Warm weather and sunny skies were a prerequisite but marketing campaigns suggested this attire was just as appropriate for backyard dinner parties as tropical island vacations. Clothing became cheaper and household budgets grew to meet a new middle-ground of affordable luxury. Clothing formerly reserved for rich people on vacation became the warm weather uniform for middle-class folks in the 1950s and 1960s. Resort lines popped up across the fashion industry that has stood as the prototype for the genre ever since.

All of the designs that popped up in the postwar resort explosion are reflected in the recent resurgence. Geometric art deco patterns of the interwar period were replaced with bold solids, floral patterns, and wide vertical stripe motifs. Ringed sleeves, contrast collars, and piping became common accents. Cabana shirts with big patch pockets on the front became popular. Waist tabs and pleats were borrowed from formal trousers for shorts with no more than 6-inch inseams. US Navy sailors returning from Hawaii introduced ornate and breezy Aloha shirts to the American public.

Another aspect that took off in the 1950s and 1960s is uniform dressing. Matching sets of shorts and shirts, sometimes even combined into a single romper design, creating a monotone look. The carefree ideal was taken a step further by removing any need to assemble matching combinations. Just as men wore a navy blue wool suit to the office, they could wear a baby blue terry cloth suit on the weekends. Plush. 

The Age of Comfort

Resort wear evolved into many different forms from the 1970s through the 2000s, many of which are fortunately lost to the consignment bin of history. Some details from the golden age of leisurewear began to return in the 2010s when practically all of menswear was informed by the 1960s. Camp collared short-sleeved shirts showed up early in the decade as men’s shorts got shorter and shorter. Aloha shirts and other vibrant patterns became popular mid-decade. By the late 2010s, terry cloth and knit polos were making a comeback, and now brands like Percival are centered on such garb. It seemed as if comfy leisurewear was creeping back into a menswear landscape that had gotten very rigid and literally constricting. Then, the pandemic changed everything.

Cruise season, as the fashion industry came to call the release of their resort lines, happens at the beginning of each calendar year. The idea still being that those who can afford to, like to stock up on new clothes for their post-winter holiday travels. All of the high fashion brands put on fancy shows and put out elaborate press releases as 2019 came to a close. The 2020 Cruise season appeared to be a full return to the post-WWII aesthetic.

Around the same time, a number of new fashion brands sprouted that were dedicated to the resort wear lifestyle. All helmed by designers that foresaw a wave of comfort coming to change menswear, but never could have predicted the pandemic that would hasten its arrival. These included the terry cloth dedicated at Dandy del Mar, the cabana shirt extraordinaires at Tombolo, and the robe revivalists at OAS. While this new vibe would have gradually slipped into the fold in the normal course of events, tragedy would see it take over menswear over the course of just a few months.

The entire planet locked down in April 2020 and fashion was irreversibly changed in the process. How and when various parts of the world came out of lockdown are far too nuanced to get into here, but to simplify the point, we’ll say that two years passed before complex social interaction began again. Over the course of those two years, pretty much everyone became accustomed to a level of everyday comfort withinin their clothing that they had never enjoyed before. Fashion and societal norms had previously discouraged the amount of sweatpants and bathrobes we all settled into. So when it came time to step out into the world again, no one was willing to sacrifice much of that physical comfort. We didn’t want to look like slobs — but a compromise had to be made.

Thus, accustomed comfort became the driving force behind the massive rise of resort wear over the past couple of years. We all looked back to a time when men dressed very comfortably yet stylishly and found the 1950s and 1960s to be the ideal balance of both factors. Picture Jude Law in The Talented Mr. Ripley, Sean Connory in Thunderball, and John Hamm in Mad Men and you’ve got the idea. Lots of soft fabrics, cut loosely with open collars and short inseams. Modern resort wear provides the comfort of pajamas combined with the style of high fashion.

Now that the resort look has fully taken hold of menswear, practically every brand is offering their own take, making the look achievable at any budget. If you can’t afford Gucci’s Cruise line, you can find an approximation from J.Crew. There is no shortage of resort wear options out there in 2023. Every man of every style preference can incorporate the free and easy comfort into their wardrobe. 

A Fortune Time to Get Dressed

Browsing through the history of menswear doesn’t show many times where comfort stood on equal footing to style. In that way, we are certainly living in a fortunate time to get dressed right now. The most stylish brands and the best-dressed guys are all refusing to sacrifice comfort to dress well. Very few positive things came out of the pandemic and lockdown but the hard reset of fashion was one of them. We all agreed to hold on to the things that we like but not the things that made us physically uncomfortable. If we learned anything it is that life is too short and too precious to not dress like we’re on vacation. 

Who is Making Top-Quality Resort Wear Today?

The Real McCoy’s Skipper shirt, available at Clutch Cafe for $240.

Universal Works Vacation Polo, available at Vestis for $148.

OAS Solid Terry Shirt, available for $120 from STAG.

3sixteen Vacation Shirt in Nutmeg, available for $239CAD (~$175USD) from Brooklyn Clothing.

Ripa Ripa Casual Linen Pant Verde, available for $155 from Brooklyn Tailors.

American Trench Cotton Linen Shorts, available for $98 from American Trench.

Sunspel Camp-Collar Printed Cotton Voile Shirt, available for $275 from Mr. Porter.

Alex Cran Cham Pants, available for $155 from Alex Crane.