The Lucrative Vacation Menswear Opportunity

In July, Heated Rivalry actor Hudson Williams was spotted in Seoul wearing a pair of calf-length white shorts from Descalco, a new swimwear brand that launches this week. Founded by Lucas di Matteo, Descalco’s name means ‘barefoot’ in Portuguese and is entering the resortwear market with a trio of tailored swim shorts.

It comes at the right time. No longer restricted to Hawaiian shirts and flip-flops, the male vacation wardrobe has matured and expanded, and men are ready to spend on it. According to data from Clearpay, men in the UK now spend 7% more than women on their vacation wardrobes — on average £420 each per year.

That spending is not necessarily going toward traditional holiday staples, but on versatile items that indicate a much broader potential for the category. As men travel more frequently, spend more time on fitness, and are more comfortable experimenting with clothing, vacation dressing has emerged as a major category, and presents a lucrative opportunity for menswear brands that can adapt.

“Men have largely moved on from an old pair of board shorts, and a suncream-stained T-shirt for the beach,” says Daniel Todd, Mr Porter’s buying director, who adds that resortwear is becoming an increased focus for the menswear retailer. “They want to look a bit more put together even when they are in holiday mode.”

Justin Felizzari, who runs Cueva, a multi-brand boutique with locations in Manhattan and Brooklyn, has noticed a big shift both in how guys vacation and how they shop for it. “They are going to nicer hotels, more luxurious properties and destinations, and they’re thinking more about how they want to look while they’re there,” he says.

Instead of buying swim shorts and a camp-collar shirt, guys are more granular with their purchasing decisions. “They are almost shopping by each moment now,” says Felizzari. “They come in thinking, ‘OK, what am I wearing on the flight, what am I wearing walking around during the day, what am I wearing to dinner?’ They’re thinking about the whole trip now rather than just saying ‘I need some vacation clothes’.”

Will Stevens, an engineer in NYC, is one of them. “I noticed over the last year or so that I was putting off regular purchases so that I was able to commit to a bigger splurge on more expensive items than I usually would,” he says, adding that he hit up Nordstrom to invest in summer-appropriate pieces from Rick Owens and JKeefer that he wore on a “trip extravaganza” around Paris, Cape Town and Stockholm.

Frescobol Carioca, which began by selling beach bats and then swimwear, has expanded into wider wardrobe categories, now spanning pajama trousers and Panama hats to suede slippers and linen tailoring. “Building the wardrobe beyond swimwear has consequently become our single biggest driver of growth,” says co-founder Harry Brantly. “Men will invest in relaxed trousers, linen shirts, knitted polos and beautifully made footwear because these pieces can move from the [holiday] back into their everyday wardrobe. The trip may trigger the purchase, but versatility justifies the investment.”

“The main thing I think about before buying [clothes] for a holiday is making sure I’m going to wear the item after the holiday, even if it is a little more adventurous,” says William Panday, a former professional rugby player who lives in London. The 25-year-old recently bought a pair of Our Legacy’s Camion mules for an upcoming trip to Greece that he hopes to wear on holiday and beyond.

Time away from the drudgery of work and routine presents a unique opportunity for men to experiment, says Shakaila Forbes-Bell, Clearpay’s consumer insights psychologist. “People actually want their clothes to reflect their identity and to help them bring out different parts of themselves,” she says. “A lot of these ideas are mostly marketed to women, so it’s about bringing men into that space too.”

For Turner Allen, a personal stylist in NYC whose clients mostly work in the tech sector, the run-up to vacation season is his busiest time of year. “A lot of my clients dress in an understated, low-key way in their day-to-day, so a vacation is really their time to kind of lean into a little bit of frivolity,” he says. “It gives men permission to have fun and almost to play a different character in a way.” His clients don’t balk at higher price points ($350+ for swim trunks from Vilebrequin), either, because the vacation experience feels special enough to justify the investment.

As fitness culture becomes more visible than ever, compounded by the pressure of social media, a vacation presents a bigger opportunity to show off hard work in the gym; no surprise that purchases for men’s sheer tops rose 107% year on year in the US according to Clearpay. “The body has become an extension of the outfit in a sense, and people are looking to really highlight the parts of themselves that they’re most proud of,” says Forbes-Bell.

As the vacation market grows, athleisure brands like Lululemon, Vuori and Alo are also upping their resortwear offerings to fill demand, but experts still see plenty of gaps to fill.

“Vacation dressing, and the high-summer delivery drops in April and May, are hugely under-potentialized within the menswear market,” says Sophie Jordan, menswear buying director at Mytheresa. To help harness its potential, the luxury e-tailer has a dedicated strategy to create vacation-ready exclusives with brands during the high summer season, and recently partnered with Brioni on a ‘Riviera’ capsule collection. “It’s been one of our most successful capsules to date,” says Jordan.

Brioni x Mytheresa Men The Exclusive Riviera Collection.

The opportunity isn’t restricted to online. Brands are also waking up to the growing opportunity to market to men IRL while they’re actually on a trip. Orlebar Brown, a menswear brand known for its beachwear, has recently expanded its outposts directly at luxury resorts like Hotel La Palma in Capri and The Ocean Club in the Bahamas, while Frescobol Carioca is available at Eden Rock in St. Barths and Le Club 55 in St. Tropez. “It’s an important acquisition channel for us,” says Brantly. “It allows us to meet customers on vacation and in the moment of need.”

After finishing up her buying appointments for the men’s Spring/Summer 2027 season, Jordan is anticipating a further uptick in the vacation offering from menswear brands come next year. “It was clear during the buying season that more brands are exploring this opportunity,” she says. “It’s smart and it’s needed. The demand is clearly there and it represents an incremental opportunity for brands to grow.”

Descalco is hoping to get in on the action. Beginning with swimwear this summer, the new label intends to expand into ready-to-wear, accessories and even cosmetics. Heated Rivalry sunscreen? A smash hit, surely.