Robinson Les Bains Swim Short, $295, F. Martin Ramin/The Wall Street Journal

WHEN RONEN JEHEZKEL, co-founder of men's clothing line Parke & Ronen, debuted his first collection of swimwear in 2002, he called it "a culture shock."

"The mass market was wearing all of the surf-inspired stuff—Hurley, Billabong, Quiksilver," said Mr. Jehezkel. "I liked to call them 'cheerleader skirts,' those big, white, baggy swimsuits." The few alternatives included Speedos and the trunks occasionally shown by high-end fashion designers, which Mr. Jehezkel described as "more runway, less for everyday."

Formerly a sea of baggy shorts and skimpy Speedos, men's swimwear is reaching new levels of refinement. John Ortved explains on Lunch Break. Photo: Getty Images.

Mr. Jehezkel and his partner, Parke Lutter, decided to take a more tailored and flattering approach. "The great shape of a man's body is the legs," said Mr. Jehezkel. "If you put on the big, long swimsuit, you're turning yourself into a barrel. But if you wear a shorter swimsuit, it emphasizes your legs and you look trimmer."

Fast-forward a decade, and men's swimwear has undergone a full renaissance. Now, there's an ocean of labels—sporty Faherty Brand, heritage-focused M.Nii and natty Orlebar Brown, to name just a few—that have relegated those oversize board shorts to the dark depths of a guy's closet, along with baggy jeans, square-toed shoes and wide ties. Men, it seems, are willing to pay a premium to look as smart and trim in their bathing gear as they do in the rest of their wardrobe.

"It's a bit like what happened with denim," said Alex Faherty, a former investment banker who earlier this year founded Faherty Brand with his twin brother Mike, an ex-Ralph Lauren designer. "Fifteen years ago, it was all Levis, whereas when you walk down the street today you see most guys wearing designer jeans. All of a sudden someone started making better products."

Fit is the main area of improvement and it's not an issue taken lightly. For the design of his trunks, Adam Brown, who launched Orlebar Brown in 2007, looked to the traditional pattern used to make tailored trousers, which involves 17 different pieces for a single pair. That detail makes the concept of bespoke swim trunks seem not so ridiculous. And such a thing does exist at newly founded New York-based company Quit Mad Stop. (To be fair, their made-to-measure shorts are relatively reasonable at $325 a pop—less than a pair of Gucci trunks off the rack.)

To further assist in the search for proper-fitting trunks, Robinson Les Bains, a French company started by Christophe Vérot in 2007, is developing a specialized size questionnaire for its website. "It's going to be quick questions—if you are short, tall, have a big belly, big butt," explained Mr. Vérot. "We're going to make it simple and fun."

While many of these designers seem to see eye-to-eye on the general idea of better-made swimwear, one dividing issue is the elastic waistband. Mr. Brown has avoided it like a crowd of jellyfish. "As a man in his forties with his clothes off in public, I want to feel confident and I want as much help as I can get," he explained. "An elastic waist pushing into my stomach is not flattering."

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One designer in the opposing camp is Isaac Ross, the founder of the new line Solid & Striped, who sees some advantage in the elastic. "The problem with a fixed waistband is that they're either a little too big or a little too small," he said. "There are a lot of different 'mediums.' You have to figure out a way that it can be fitted." One solution that many brands use is a drawstring unobtrusively tucked inside a buttoned flat waistband. Orlebar Brown puts two adjustable tabs with silver buckles on its trunks.

Though these trunks have price tags that are typically triple those of the saggy board shorts, it doesn't seem to hinder their marketability. Bloomingdale's men's fashion director Josh Peskowitz explained that paying more for nicely fitting trunks is just a part of the larger trend of men spending more time and money on their wardrobes. "If they're investing in the right jeans, the right tie, the right suit and the right sneakers," said Mr. Peskowitz, "of course that's going to extend to swimwear."

Seekers of swimwear will be spoiled for choice. Each brand has its own special twist. For M.Nii, revived last year by John Moore, it's a storied heritage. In the 1950s, the company made some of the first surf shorts, called Makaha Drowners, for the big-wave surfers. The shorts were also worn by the likes of Elvis Presley, Gary Cooper and John Wayne. "We have an original invoice for JFK, who got his pair in 1959," said Mr. Moore. "It actually says: 'To be sent to the U.S. Senate.' "

Of course, because men are lazy, practical creatures, one major appeal of the new genre of swimsuit may be versatility: You can wear these trunks as regular old shorts, even when you're nowhere near a body of water. That was one of the main reasons Orlebar Brown's Mr. Brown launched his label. "It's a short you can swim in," he said. "Not just a swim short."

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