I read this on the subway this morning and was going to post it here myself. I'm not a fan, I like it with jeans, but not dress pants unless the shirt is perfectly tapered and squared off at the bottom (is that the correct term?). I also think this looks awful on men under 6 feet. Here is the article for those who don't want to register: July 20, 2004 Flying Shirttails, the New Pennants of Rebellion By GUY TREBAY Daniel Peres is a slob, and that is meant in the nicest possible way. The editor in chief of the men's magazine Details, Mr. Peres is living proof that casual Friday never really disappeared. He is the sort who wears Converse All Stars with his rumpled Helmut Lang suits and keeps his hair combed in a postnap tousle that is no cinch to achieve. Mr. Peres makes no claims to style paragon status, but in one way, at least, he is at the vanguard of what looks like a trend. He almost never tucks in his shirt. "Day, night, all situations, it's out," he said. "O.K., maybe for a funeral I would tuck." This may be remembered as the summer when new sartorial frontiers in the workplace were definitively breached - and in a manner destined to agitate bosses and parents everywhere. Men are letting their shirttails wave, a fact true not just of polo shirts or square-cut tropical styles designed to be worn outside of trousers but of broadcloth dress shirts with tapered tails never meant to see light of day. Draped over khakis or jeans or expensive dress pants, the tails-out look appears to be the default for a generation still searching for a middle ground between the traditional coat-and-tie uniform for the workplace and the Internet-era alternative of outfits best suited for mowing the lawn. And, although retailers insist that the style is pitched mainly toward the young, the trend has obvious benefits for male Baby Boomers forced to confront, conceal and, if possible, flatter what an advertisement for women's undergarments used to term "midriff bulge." Employers may have pushed back the casual Friday look of a decade ago, concerned that sloppy dress correlated with shoddy output, but the march of casualization is not so easily stopped. Influenced, perhaps, by the crisp Latin American guayabera or by the adolescent ease of urban hip-hop clothes, the untucked dress shirt may not yet have made inroads at law offices or financial institutions. But the style is well-entrenched in Hollywood executive cadres - at the lineup on stage at a screening of the Harry Potter movie in New York last month nearly all sported the look - and among influential fashion types. Seated in the front rows at Dolce & Gabbana, Gucci, Burberry and dozens of other presentations during the recent Milan men's wear shows was a posse of men whose occupation is instructing American men how to think and what to eat, buy and wear. Besides Mr. Peres, there was Jim Nelson, the editor in chief of GQ; Nick Sullivan, the fashion director of Esquire; Bruce Pask, the style director of Cargo; and Joe Zee, the editor in chief of Vitals, a shopping magazine from Fairchild Publications that will have its debut this fall. To a man, they wore their shirttails untucked. "It's a kind of nonfashion fashion look," Mr. Zee said. "All the young Hollywood types, the young heroes who are cool, like Jake Gyllenhaal, Orlando Bloom and Spike Jonze, wear their shirts untucked. It's one of those looks that's meant to seem like there's no effort, although we know that it's really thought out." It is so considered, in fact, that designers build the look into their collections. "It's just much cooler to have it out," Tomas Maier, the creative designer of Bottega Veneta, said one morning. Atop his own $730 cotton chino biker pants and fringed suede moccasins, Mr. Maier wore a pricey cotton Bottega Veneta shirt with the tails left out. "It's like men wearing shoes with no socks," he said. "There is the same shift in how men wear their clothes to be casual rather than all tucked in and tidy. It is a style that wouldn't work in the boardroom, but pretty much anywhere else it would look really cool." Men wearing khakis or suits or jeans and with their broadcloth shirts tucked in look boring or worse, said Michael Macko, the men's fashion director at Saks Fifth Avenue. They look like the late Tony Randall, natty but distinctly of another time. "It's going to sound contradictory, since everyone is talking about dressing up again, and young kids are wearing blazers," said Mr. Macko, whose current Fifth Avenue windows display the first of the fall suits and jackets, all shown over untucked shirts. "There is something about being untucked and more casual that guys find rakish and appealing," he said. "It's bucking the system with a bit of rebellion but in a very Polo, very John Varvatos way." For those who lack the confidence to leave their shirttails flapping entirely, designers like Mr. Varvatos have provided a compromise, in the form of the half-tuck, a styling gimmick ubiquitous in men's fashion magazines and at any of the relentlessly hip nightspots in Manhattan's meatpacking district. "The half-tuck is very safe, and it does look like you put some thought into it," said Mr. Macko, whose current uniform runs to pinstriped suit pants worn with a half-tucked shirt and red leather Birkenstocks. Gustavo Rangel, a salesman at Saks, who was wearing his own shirt neatly tucked in front and hanging loose behind, explained the style. "It's a little bit more of a statement," said Mr. Rangel, referring to the custom of scrunching a bit of shirt behind a belt buckle and leaving the rest of the tails to drape. "You have to learn how to show it in a clean way. You don't want to wear an oversized shirt, or it's a little too much." It is too much and also too old, said Mr. Peres of Details, although not as dowdy, apparently, as a shirt that is fully tucked. "Particularly now that the campaign is heating up, guys in suits with their shirts all neatly tucked in just look so obvious and clichÃ©d," he said. They look as if their parents had laid out their clothes. And in a sense, they have. On the road to adulthood, there are many concessions to the loss of boyhood's joyous dishevelment. Tucking in shirttails is an early and crucial one. For decades, the sartorial establishment took the part of Mom and Dad. Tucked shirttails looked neater, experts said. They were more efficient, suaver and also, it should be noted, kept one from being taken for the pizza guy. That, of course, was before the dot.com boom and before Jimmy Buffett made it stylish in certain quarters to wear shirts that billowed and luffed like spinnakers. The reasons behind the tucked shirt's long sway over dress codes are not complicated. Tucked shirts were an essential component of the soft coat of armor that is the suit. "The suit is a streamlined and durable uniform that has survived for centuries," said the art historian Anne Hollander. Central to the idea of streamlining was the elimination of unnecessary loose ends, lengths of cloth to get hung up on doorknobs or, for that matter, pikestaffs. Freudians might see sexual connotations in the decision to leave shirttails hanging, but almost anyone would agree that an untucked shirt is, at some level, the uncomplicated expression of every man's inner slob. And that is why parents insisted that one tidy up, a viewpoint that some retailers, at least, are hoping to see stage a return. "I particularly dislike it when you see the tail of a dress shirt hanging low," said Michael Bastian, 38, the men's fashion director at Bergdorf Goodman. Mr. Bastian views the tucked shirt as an important point on the continuum of gentlemanliness, an evolution that begins with learning to knot one's shoelaces, shake hands confidently and look other people in the eye. "We're not down with the untucked thing," he said. "I personally don't understand it, but guys under 30 certainly seem to think it's cool."