Let’s Dress It Down, Ari

Half a century ago in Hollywood, men conveyed power simply: typically with a black suit, ideally tailored by Jack Taylor, whose shop—snuggled up to Spago on Cañon Drive in Beverly Hills—remains a white-carpeted testament to a time when the loaded word “metrosexual” wasn’t necessary to describe a gentleman who knew a thing or two about grooming.

In the 1940’s, fledgling mogul Lew Wasserman instituted the combination of black sack suit, white Sulka shirt and skinny black tie at M.C.A., the talent agency which he was then running. M.C.A. agents subsequently became known around town as the “M.C.A. mafia.” (Mr. Wasserman didn’t abandon this penguin shell when he ascended to the role of studio head at M.C.A./Universal in 1962.) In the 1970’s, C.A.A. founding father Michael Ovitz, who idolized Mr. Wasserman, continued the tradition at his agency, where the black Armani suit became the unofficial uniform in which to slay enemies over gross points.

But as American fashion has relaxed into the cozy comfort zone of rumpled khakis and distressed T-shirts, so, too, has the Hollywood dress code. Today, Universal president Ron Meyer can often be spotted in jeans, as can Columbia Pictures head Amy Pascal. Toby Emmerich, president of production at New Line, is another denim devotee, and fond of padding around his office in white athletic socks—his Labrador, Bear, a few luggish paces behind. Even entertainment lawyers, traditionally Tinseltown’s most buttoned-up caste, have no qualms dining at West Hollywood’s Pane e Vino in T-shirts.

Make no mistake: The symbolism of power has not been lost in this industry-wide dress-down. But it’s been radically altered. In the same way that producers and studio execs regularly prop their feet up on tables and sofas in order to simultaneously convey the messages of a) I’m not a suit—I’m a creative!, and b) If you had as much influence as me, you could do this, too!, casual dress separates those who can wear whatever they damn well please from those who can’t.

Amazingly, there’s still one remaining citadel of old-fashioned civility—or, depending on how you look at it, one last group of suckers. Agents remain the only group left in Hollywood that still adheres to a professional, if unofficial, dress code, making them an anachronistic curiosity as they march down Wilshire Boulevard en masse at noontime—an orderly squadron of charcoals, navies and blacks—headed in the direction of Barney Greengrass (here, a chichi place at the top of Barneys Beverly Hills) or Mr. Chow. They’re like displaced refugees from Wall Street, dabbing at their dampened brows with Brioni handkerchiefs—a feeble attempt to combat the unforgiving glare of the Los Angeles sun.

But in recent years, the Egyptian cotton has begun to fray around the edges a bit. Though suits are still the standard at the Big Five agencies (C.A.A., William Morris, I.C.M., U.T.A. and Endeavor), fewer ties are showing up at the office, especially as the weekend draws near. William Morris even observes Casual Friday. According to a spy at Endeavor (the model for Ari Gold’s former place of employment on HBO’s hit show Entourage), partner Adam Venit regularly wears khakis and polo shirts— throughout the week. Ari Emmanuel, the model for the Ari Gold character, is a Friday jeans kind of guy. (Neither man wished to comment.) Things are getting more and more lax at U.T.A. as well, according to several employees. C.A.A., which has a reputation as corporate and sleek as its I.M. Pei–designed headquarters, remains the only agency whose employees are respectful enough, or paranoid enough, to adhere to five full days of jacket and tie.

White Jeans at William Morris

At William Morris, the good ol’ boy 10-percentery whose image is still colored by memberships at the Hillcrest Country Club on Pico Boulevard, cigar-smoking sessions and day-long games of pinochle, things first started to slouch toward dishevelment in the mid-1990’s, when former president Arnold Rifkin—despite his personal fondness for Armani—introduced Casual Fridays.

This was a dramatic shift from the way Rifkin’s predecessor, Jerry Katzman, ran the ship. “I always felt that you looked a lot more professional if you dressed professionally,” Mr. Katzman said in a telephone interview. “That the creative side of the business could dress however they wanted, but that agents were really representing talent, and they were the business side of the agenda.”

One veteran W.M.A. agent who wished to remain anonymous (the agency biz can be a bit like the Gestapo when it comes to the press) recalls attending a staff meeting during the Katzman era on the day before Thanksgiving. Because the agent was getting on a flight in the afternoon, he wore jeans and a black turtleneck.

Upon taking his seat at the conference table, Mr. Katzman, seated at the head, stared icily at the agent before asking: “How far do you live from here?”

“The question just dropped in the air. Everyone knew what it meant—that I should go home and change,” the agent said. “I was terrified.”

Mr. Katzman relaxed a bit when he was told about the flight.

In 1999, the bar at W.M.A. was lowered further with the arrival of David Wirtschafter, now president, who schleps around the agency’s hallowed halls in a positively Kurt Cobain–esque ensemble of faded jeans, work boots and flannel shirts, according to one colleague; another cited “flip-flops, jeans, athletic stuff—T-shirts and sweatpants.”

“He always did it, and nobody ever stopped him,” Mr. Katzman said. “I think that’s his personality.”

To the bewilderment of Mr. Wirtschafter’s colleagues, W.M.A. chairman Jim Wiatt, a sartorial stickler who’s known for his aversion to facial hair—“What are we selling, refrigerators?” the agent scolded one employee sporting a 5 o’clock shadow—looks the other way. (Mr. Wirtschafter, perhaps understandably wary after his unusual candor in a New Yorker profile blew up in his face, declined to discuss his style choices with The Observer.)

These days, W.M.A. agents are more likely to confuse Hillcrest for a hot new bar on Melrose. When it comes to clothes, they favor pale blue button-downs (staff meetings are often a sea of powder blue) and simple ties, affecting the look of overgrown prep-school boys whose weekend plans lean toward Palm Springs—as opposed to Vegas, the destination of flashier types from C.A.A. and Endeavor.

On Fridays, however, staid decorum gives way to misguided creativity. “The Casual Friday thing is a disaster, because a lot of people who try to do it—it’s pathetic,” said one high-level W.M.A. agent. “One of my associates comes in with white jeans and a big, oversized shirt—a long-sleeved button-down that looks like it’s his dad’s shirt. He looks like a farmer. He’s trying to look cool and hip, and it’s down to his knees …. The trick is how you pull off the casual part and look decent.”

Mr. Katzman marveled at the current relaxed environment. “Even Arnold was not a casual kind of person,” he said. “Casual Friday meant that you didn’t have to have a tie! It didn’t mean that you could come in in jeans and a T-shirt.”

(Luckily, we have Anna Wintour to whip these slackers into shape: high-rollers at William Morris received free copies of Men’s Vogue when the magazine launched earlier this month.)

Members of the establishment aren’t the only ones who’ve been rolling up their sleeves lately. In July, Paradigm—an up-and-coming agency that earlier this year swallowed Writers & Artists and has been rumored to now be eyeing I.C.M.—had its first-ever dress-down day. “People were mostly wearing a lot of jeans, polo shirts—everyone kind of looked the same,” said a spy. “You could tell right away who had some style and who just didn’t have a clue. A couple of people had flannel shirts tucked into their jeans—kind of dorky. It was revealing. A couple of the male agents looked incredibly thin, like a little boy. Very skinny.”

According to Leslie Kaufman, a personal shopper in the men’s department at Barneys Beverly Hills on Wilshire Boulevard, suits haven’t exactly been flying off the racks for her agent clientele in recent years. “The agency business used to be much more prominent,” Ms. Kaufman said. “With the advent of going to casual office days, there’s been a big change in the suit business.”

Whether the fall will bring an uptick in sales remains to be seen. “Our season has not quite started,” Ms. Kaufman said. “September just deals with Labor Day and the High Holy Days and the Emmys.”

Ian Daniels, who owns a discount men’s-clothing warehouse in Santa Monica from which he supplies agents and other Hollywood “clotheshorses” (such as the permatanned actor George Hamilton) with marked-down Kiton, Borrelli and Cesare Attolini garments, said that his clients are increasingly looking for “crossover” attire, or things that can be worn both at work and at play. Mr. Daniels is a strong believer in “casual elegance,” he said on a recent afternoon, looking like a 21st-century Don Johnson in an untucked pink Barba shirt, white Borrelli pants and Prada Sport loafers without socks. “I think there’s way too many guys running around in jeans and T-shirts,” he said. “Instead of dressing like grown men, they’re dressing like kids.”

Spit ’n’ Shine at I.C.M.

A few members of the old guard are still carrying the torch of formality. I.C.M. president Ed Limato, a flamboyant iconoclast who brings to mind both the late George Plimpton (whom he somewhat resembles) and Elton John (a client), keeps the ranks in line at I.C.M.—even though at his famed pre-Oscar party, Mr. Limato goes shoeless.

“I’m the holdout,” Mr. Limato said over the telephone in a baritone voice that allows no letters to escape unenunciated. “I wear a shirt and suit every day, and I expect everybody else to. As long as I’m here, that’s the way it’s going to be. It’s a business and you represent talent, and I don’t think talent wants to see their agents dress like their best buddies. I think they think of the agents as people who represent them. I think they want to see spit and shine.

“I don’t believe in—what did you call it?— Casual Friday,” he said disdainfully.

According to an observer, when Mr. Limato spotted a female employee wearing culottes once, he gasped in horror: “Clam diggers!” On another occasion, when an agent entered his office without any stays in his collar, Mr. Limato cried: “You’ve forgotten your bones today!”

When Mr. Limato spies an agent who doesn’t live up to his standards of tailoring, a company-wide e-mail is fired off, reminding agents that no day is Casual Day. According to several sources, Mr. Limato is also known for sending out e-mails directing that if agents’ window blinds aren’t fully deployed, they should be three-quarters of the way down, in order to preserve a look of unity from the sidewalks of Wilshire.

(Mr. Limato denied any fenestral preoccupations. “When you’ve been here a long time, you hear things that add to the color of the person,” he said with a chuckle. “There’s nothing to that.”)

Of course, boys will be boys.

“If Limato’s in town and you come in on a Friday, you’ve gotta be smart about it,” one mid-level male I.C.M. agent said. “Often I don’t wear a tie on Friday, and I usually don’t shave on Friday.”

He added, sotto voce: “I’ve had two days of growth and been able to get away with it!”

Said one former I.C.M. agent about the agent-suit relationship: “Jeff [Berg, chairman of I.C.M.] once said to me that one of the reasons he liked the company to dress up was that if a client makes $20 million a picture, then in the office that means we make $2 million off them. ‘So I think you can get dressed up for them,’ he said.

“All things agency-driven are anxiety-, fear-driven,” the agent continued. “One of those [fears] is that you might lose a client if the client thinks for a second that the person taking care of them isn’t dressed to the nines and a complete business man.”

But this fear may be unfounded. Luke Greenfield, who wrote and directed The Girl Next Door, and who is represented by Philip Raskind, an Endeavor agent and partner, said, “I’ve never seen Phil not in a suit, but if he did show up in flip-flops and a Hawaiian shirt, I’d love it. Especially in a creative environment, everyone needs to relax.”

He paused. “If he was dealing with my back-end [gross] and quote, maybe it would be a little disconcerting.”

Then again, not all agents are complaining about an enforced dress code. “I actually feel more comfortable in a suit,” said one U.T.A.’er. “I like a division between what I wear on the weekend and what I wear to work.” The Casual Friday hater from W.M.A. concurred. “I personally wouldn’t want to be repped by someone who wears a T-shirt,” he said.

Female agents have it both better and worse. On the one hand, they have greater latitude in interpreting the definition of professional dress. “As a woman, we have a teeny bit more leeway, because it’s not about always wearing a power suit,” said one Endeavor agent in her 30’s. “A woman can get away with wearing a great T-shirt and a skirt, whereas no man can wear a great T-shirt.”

Yet when the workday ends and it’s time for premieres or work drinks, women are stuck in their limbo attire—not quite banker, but not quite urban chic, either. “I never go out in my same clothes,” said one female I.C.M. agent. “I just feel uncomfortable. I always bring a pair of jeans and change in the bathroom. I’ll wear whatever—a blouse and blazer with jeans and my pumps.”

Joe Rosenberg, formerly of C.A.A. and now an executive at Radar Pictures, is one of those frowning on agents in T-shirts. “From a client’s point of view, they’re handling your business and they’re out there speaking for you, and I think you want someone to be, as a human being, professional in who they are and how they say what they say, but also to look the part,” he said.

On a recent weekday morning, Mr. Rosenberg paid a visit to Jack Taylor, the 89-year-old Russian-born Beverly Hills clothier, whose handmade suits start at $3,200. Black-and-white photos of former clients Cary Grant and Jack Lemmon were hanging on one of the shop’s walls. Legendary former William Morris president Abe Lastfogel was also a customer.

Dressed for work—orange cashmere sweater, faded jeans, gray New Balance sneakers—Mr. Rosenberg picked out fabric for a new suit and bantered with Mr. Taylor, small and natty in velvet slippers. Then the younger man left the store.

Seated at his paper-strewn desk, Mr. Taylor shook his head and closed his eyes behind his enormous Wassermanesque, black-framed glasses.

“Did you see him?” he said, his voice softly hoarse. “That’s the way they all dress. It’s terrible.” Let’s Dress It Down, Ari