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Swim-trunk maker Vilebrequin’s eye-watering prices come from the European provenance of the polyamide fabrics, sourced in Italy, woven in France and resilient against sun, salt and chlorine.Marc Schwartz

At some point in the process of shopping for swim trunks, many of us will be forced to choose between the desired pair and the vacation itself. You'll be flicking through suits of indistinguishable quality when the prices suddenly jump from $40 to $75 to … $300.

A woman who has been lulled into a false sense of prosperity by mid-range brands such as J. Crew, Quiksilver and Lululemon can only clutch her freshwater pearls in alarm. Women's swimwear has a delicately complicated job that makes the top end of a wildly diverging price range almost understandable. But what are men's trunks if not synthetic boxers lined with tank-top mesh?

Blasphemy, says Roland Herlory, CEO of Vilebrequin, the French brand that sells a thousand-dollar hand-embroidered swim trunk with no-stitch hypoallergenic lining and zinc aglets. The man who defends the quality of his aglet – drawstring tip, to the layperson – is a man who doesn't suffer fast-fashion fools.

Herlory is nothing if not passionate. A veteran of Hermès, who convinced both companies to let him work remotely from his home in St. Barths, he rhapsodizes like a Caribbean Karl Lagerfeld about the "life-changing" qualities of electrostatic-free brushed yarn and the "elegant allure" of well-draping fabric.

"When you're half-naked on the beach, the drape must be perfect," he says in a velouté-thick accent. "If the fabric is thin, it sticks to your leg and when you get out of the water you look like nothing."

Vilebrequin's eye-watering prices come from the European provenance of the polyamide fabrics, sourced in Italy, woven in France and resilient against sun, salt and chlorine. They're just the right thickness to drape consistently whether wet or dry and the waist elastic is of the highest grade. The colourfast printing is performed in France and Italy by specialists in brushed polyamide, of which there exist only three. Seamstresses hand-stitch the pockets so the patterns match precisely, like wallpaper.

Launched in the 1970s as an homage to decadent Riviera living, Vilebrequin dominated the market for prestige swim shorts for decades. But men's attitudes toward fashion – and spending on fashion – caught up, while luxury travel became a year-round sport played on every continent. By 2012, when apparel group G-III acquired Vilebrequin for $150-million (U.S.), it had been joined by upstarts like Le Slip Français and Orlebar Brown.

"Holiday was always seen as an off-duty moment. We now find ourselves in a place where men are considering what they wear for every occasion," Orlebar Brown founder Adam Brown says. Today, with Instagram documenting every spare moment, he adds, looking pulled-together during leisure time is key.

When OB launched a decade ago, the men's swimwear offering was flooded with baggy bottoms that wouldn't stay up, so Brown designed "a short I could swim in," inspired by images from the original Talented Mr. Ripley, and the mid-century photographs of Slim Aarons (the top-end styles, at $370, are printed with Aarons's photographs, specially formatted in 360 degrees). He says he found it ludicrous that he'd have to change clothes just to go to the hotel bar.

Harry Brantly, co-founder of Frescobol Carioca, marvels that this attitude was so slow on the uptake. "It was ridiculous that there was only one luxury brand in the market when we are all going away more," the part-Brazilian former financier says. "We winter in St. Barths, we have three to five summer holidays a year. Even when we're skiing we go to the spa after."

Offering a glimpse into the rarefied circles he moves in, Brantly adds, "I'd show up on holiday with 10 pairs of Vilebrequin swim trunks and every guy there was the same."

Frescobol Carioca launched in 2009 with a line of Brazilian frescobol beach paddles, then expanded into swimsuits after an infusion of cash from fashion photographer Mario Testino. Brantly consulted with a Savile Row tailor to get the shape right, and sources his polyamides in Lake Como – he insists they're thinner and faster-drying than Vilebrequin's. He's considering adding stretch into the weave, "so it has some give when you're going for a low backhand in tennis."

Assembled at the same Portuguese manufacturer as Victoria Beckham's fashion line, the button-fly trunks, starting at $240, sell out of the most exclusive shops in Ibiza, Santorini, Palm Beach, Dubai, Mustique … everywhere except Brazil, where Brantly concedes there is little market for such extravagances.

Orlebar Brown's chlorine- and saltwater-tested French polyamide shorts have a four-part shaped waistband (a Savile Row standard) and heat-resistant Zamak metal hardware. They're also guaranteed for five years, which goes some way to explaining the price tag.

Though Vilebrequin has no such guarantee, longevity is implied. Herlory sees the shorts as talismans – souvenirs, in both languages, of happier times.

"When you open your closet and glance just a fraction of a second, you're reminded of your holiday in Portofino when your kids were 10 years old and you were wearing that same pattern," he says. "These are the best moments of the year."

If, for that kind of money, you expect your swimsuit to go from pool to bar and several steps further, let Herlory suggest Vilebrequin's new Tuxedo model ($360), with gold-metal fastener and satin side stripe, "so you can get married in it."

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