What man, as the weather warms, does not dream of jettisoning his tie and jacket? Even for many devotees of the power suit, the switch-over to short sleeves and lighter fabrics can't come soon enough.

Unfortunately, this sort of seasonal informality doesn't work for everyone. It's forbidden in a lot of offices. Worse yet, it's unoriginal. These days, men who want to shed clothing and make a statement are looking downward. They're losing their socks.

They are not the first. Throughout history, plenty of their stylish predecessors have cut a fine figure without the benefit of socks—Ernest Hemingway and Sir Roger Moore are but two high-profile examples. Beyond a disregard for blisters, this purposeful act of neglect conveys a certain comfort—bordering, perhaps, on satisfaction—with oneself, whether it's being adopted by a continental swell

or a no-frills man of action.

Traditionally, this much was true of the leisurely sockless look: It was something you did on your own time. Several years ago, though, it took its first strides into the workplace. Thanks in large part to the designer Thom Browne, more than a few stylish professionals now take client meetings in cropped suits, expensive brogues and unabashedly naked ankles.

SUMMER PARTY | Traditional seersucker, a little ankle and white bucks is a dashing dressed-up look. (Thom Browne New York Cotton Seersucker Suit, $2,220, barneys.com; Neil M Cambridge Oxford, $170, endless.com) F. Martin Ramin for The Wall Street Journal, Styling by Anne Cardenas

But even as those same trendsetters now rediscover hosiery, the sockless game they launched is well afoot. As the style settles in, the old jokes ("Hey, laundry day?" "Ford a river on the way over?") start to sound passé. And this time of year, they can come across as downright clueless.

This May, when the actor Josh Hartnett strode into a New York museum benefit in a trim suit and a narrow pair of Prada cap-toe oxfords, sans socks, he seemed a bit surprised to be asked to explain his reasoning. "Why do I do it? Because it's summer and we're allowed to, and it's a little bit more casual," he told a reporter.

After all, certain in-crowds have been foregoing socks for decades. "The exposed ankle has to be the ultimate visual metaphor for those Ivy League notions of moneyed leisure and relaxed elegance," Graham Marsh and J.P. Gaul wrote in "The Ivy Look." For a northeasterner who knows his way around a boat, slipping sun-tanned feet straight into Sperry Top-Siders, canvas sneakers or even penny loafers comes as naturally as hoisting a jib.

Nearer to the equator, the style is even more ingrained. Growing up in Havana and Palm Beach, "I don't remember anybody ever wearing socks," said Percy Steinhart, founder and designer of the upscale resort footwear company Stubbs & Wootton. "It's sort of tacky to wear them in the tropics, I guess," he added. And in parts of Italy, men's shoes and bare ankles go together like Campari and soda.

OUT ON THE TOWN | Traditional slippers, a bare foot and trim Nantucket reds: pure Spanish fly. (SF Tapered, $98, dockers.com; W Black Linen, $425, stubbsandwootton.com) F. Martin Ramin for The Wall Street Journal, Styling by Anne Cardenas

But away from the pool, marina or Amalfi Coast, the sockless look conveys a hint of non-conformity. "It's a little act of rebellion," said stylist, consultant and former Saks Fifth Avenue menswear director Michael Macko. Certainly that's what Andy Warhol, no great fan of socks, had in mind. And while the bare-ankled account manager turns more heads than his colleague in the open collar, he is also less likely to be in violation of corporate dress code.

"It transmits and advertises a little bit of accessibility," suggested Sid Mashburn, who goes sockless every day in his eponymous Atlanta menswear shop. Mr. Mashburn explained that he and his multigenerational staff (all of whom regularly go bare-ankled at work) don't recommend the look for everyone. "Some guys are not ready to go sockless," he said. "And if you came in and said you were going to a job interview, I would strongly advise you to wear socks."

The odor issue is not one to be sniffed at either, although advocates of the sockless look insist that foot powder and a sensible shoe rotation (not to mention vinegar, deep-freezing and other preventive measures) keep bacteria at bay. And even if one is dutiful about using wooden shoe trees, Mr. Macko said, "you have to be prepared to ruin your shoes."

BUSINESS CASUAL | Let all the guys at the office know you're cool on the weekends with a dress-sockless oxford. (Black Fleece by Brooks Brothers Grey Trousers, $450, blackfleece.com; Darby II, $1,265, johnlobb.com) F. Martin Ramin for The Wall Street Journal, Styling by Anne Cardenas

Admittedly, the disincentives can be daunting. Lately, however, sock makers have stepped forward with a solution of sorts. Long popular in Italy, where they are known as fantasmini, low-cut "invisible socks" are now being offered by the likes of Nike and Banana Republic. About a year ago, Goldtoe introduced a sock that ends well below the ankle and clings to the heel by means of an adhesive heat gel. "Instead of fighting the trend, we decided to go with it," explained Matthew Mull, the company's director of design.

Mr. Mashburn, the Atlanta store owner, said he sells only wool socks, citing their superior breathability over cotton, and has no intention of carrying invisible socks anytime soon. "It's not about the affectation of the look, it's about being sockless," he explained. "If that's a real stretch for a guy, he probably shouldn't do it."