Original headline: “Untucked Shirttails, the New Pennants of Rebellion,” from July 2004.
A new normal: Strange how some fashion fads that seem destined to last for months somehow endure for decades. The backward baseball cap, for example, blew up as a rebellious teenage fashion flourish in the 1980s, but instead of going the way of acid-washed jeans and Members Only jackets, the look evolved into a bedrock element of the bruh uniform for 30 years running. Every bit as rule-flouting, but even more ubiquitous, is the untucked dress shirt. This seemingly fleeting fashion trend attracted arched-eyebrow skepticism in this Styles article by Guy Trebay, which appeared on the front page of this newspaper at the peak of mid-aughts metrosexuality. “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,” Mr. Trebay wrote. “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.”
Winds of change: When it comes to launching a style trend into the mainstream, it takes an army of influencers, and the untucked shirt managed full mobilization. By 2004, fashion-forward editors like Jim Nelson of GQ and Nick Sullivan of Esquire, along with seemingly every male celebrity under 50, were doing their best to make respectable this once-slovenly look, which also happened to dominate the front rows of the Milan men’s wear shows that year. “It’s a kind of nonfashion fashion look,” Joe Zee, the well-traveled style editor, told Mr. Trebay in 2004. “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.”
The deeper context: Men under 30 might find it strange that anyone other than cops, accountants and Capitol Hill types ever tucked in a button-down shirt. But for decades, the untucked look was relatively rare on the fashion landscape, outside of slumming college students and madras short-clad preppies summering in Nantucket. O.K., the look had some precedent in American culture: the more rebellious of the bobby soxers, those rebellious teenage girls of the early Sinatra years, shocked grown-ups nationwide by rocking untucked shirts along with rolled dungarees, saddle shoes and, obviously, bobby socks. Among men, however, flapping shirttails were relatively rare. Even rock ‘n’ roll iconoclasts like the Rolling Stones of the 1960s and CBGB-era Blondie of the 1970s tended to politely tuck in their button-downs. That all began to change, however, in the casual-everything, dot-com era of the late ’90s. Suddenly, sneakers and hoodies transformed into office wear among proto-Mark Zuckerbergs. Even Wall Street banks and law firms dallied, fairly risibly, with “casual Fridays.” By the middle of the next decade, the untucked shirt became 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,” Mr. Trebay wrote.
A new generation gap: This is not to say there was no pushback. “For decades, the sartorial establishment took the part of Mom and Dad,” Mr. Trebay wrote. “Tucked shirttails looked neater. They were more efficient, suaver and also, it should be noted, kept one from being taken for the pizza guy.” The squares, however, were destined to lose this battle. As much as employers initially pushed back against casual clothing in the workplace, “concerned that sloppy dress correlated with shoddy output,” the “march of casualization is not so easily stopped,” Mr. Trebay concluded. “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.”