Who dresses Zendaya, Sebastian Stan, Jill Biden? Stylists on the pressure ahead of Oscars

Once, stylist Bailey Moon was dressing a female client for a major event. Moments before she left her hotel, a piece of tile, used as embellishment, fell off. Having handled hundreds of situations like this in his career, Bailey leapt into action with some hot glue. The problem was that, while he succeeded in reattaching it to the dress, he had also accidentally glued himself to the garment, too. And thus he found himself in the sleek town car with the actress, on the way to her engagement, desperately trying to get himself unstuck. Suffice it to say, he managed to disengage from his client’s garment before she hit the step and repeat, but he did not relish the moments of mild panic. “My thing is to not have this chaotic atmosphere,” says Moon, who dresses actors like Cristin Milioti, Diane Lane, and the married couple Rebecca Hall and Morgan Spector. He also works outside the entertainment industry, most notably with Dr Jill Biden – the former first lady of the United States – and other members of the Biden family. “I know some stylists who love that adrenaline rush of, ‘We have five minutes, and we have to sew the dress together.’ I refuse to do that.” “But,” he added, “it doesn’t always work out that way.” Welcome to the high-stakes and sometimes hectic world of celebrity styling. Although the result is undoubtedly glamorous, getting there can be anything but. View this post on Instagram A post shared by Bailey Moon (@bailey.moon) Behind each necklace, dress and tuxedo there lies a lot of hard work: countless emails and phone calls to coordinate logistics, hours logged driving across Los Angeles or New York, negotiations for money and coveted one-of-a-kind gowns, cross-country or international flights and more carrying of overstuffed garment bags than seems humanly possible. And as Hollywood’s biggest night approaches, the ante gets nudged ever upwards. “If you have a nominee, it does get crazy,” says Michael Fisher, whose clients include Jake Gyllenhaal, Oscar Isaac, Bowen Yang and Sebastian Stan, who is nominated this year for an Oscar for best actor. “If you have multiple, it’s even crazier.” Today, he says, it is not just the Oscars or Emmys themselves, but the slog of events that lead towards them. “All the lunches, the breakfast, the teas, the festivals, the Q&As. You go through a really intense boot camp as they’re campaigning, and then once the nominations start locking in, it’s almost like resetting, going back to ground zero and starting all over again.” View this post on Instagram A post shared by Bailey Moon (@bailey.moon) “Have I cried? Yes,” says one stylist who prefers not to be named. “Have I been yelled at? Yes. It’s very rare that there’s really crazy drama, but I’ve definitely had moments where there’s a pile of couture on the floor of my studio, and I look around and think, ‘What is my life?’” Dressing celebrities has become something of a cottage industry. Stylists at the top of their game can be well compensated, but much like the actors they work with, their incomes can vary dramatically depending on client or project. For example, it is customary that stylists are paid “by look” when outfitting an actor for the press cycle of a movie or television show, including premieres, interviews and talk show appearances, a fee that generally ranges from US$1,000 to US$5,000. These fees are often paid, at least in part, by the studio overseeing the project, although sometimes the actors subsidise them. In some cases, deals are struck for entire press cycles, or clients keep stylists on a monthly retainer. For high-profile events – the Oscars, Emmys, Grammys and Golden Globes – top-tier stylists dressing top-tier talent can make in the mid-five-figure range, with stories of US$100,000-plus fees floating around. View this post on Instagram A post shared by Bailey Moon (@bailey.moon) Brands have also been known to pay the talent to wear their clothes to these types of occasions – something that can bring in fees in excess of US$100,000 – an arrangement that extends to jewellery and, for men, the lucrative business of luxury timepieces. “The fashion-entertainment relationship is more important than ever,” Moon says. “That’s why UTA [United Talent Agency] and WME [William Morris Endeavor] have fashion divisions now.” This recent push by major talent agencies to create fashion-specific departments is intended primarily to represent stylists, photographers and designers such as Loewe’s Jonathan Anderson, who created costumes for last year’s Challengers and Queer, both directed by Luca Guadagnino, and then outfitted these films’ male stars for their buzzy press tours. But these agencies can also help broker deals between brands and talent. Moreover, the agencies can help the stylists and clients convert these red-carpet relationships into something more long-lasting and financially lucrative, such as spokesman deals or brand ambassador roles – think of Zendaya’s association with Louis Vuitton and Harris Dickinson starring in this season’s Prada advertisements. These deals are, in many ways, the most desirable of all and can, under the best circumstances, yield seven-figure payouts. Although awards season is their busiest time of year, stylists do not work only for the super famous. Up-and-coming actors can seriously boost the profile of their on-camera work with successful red-carpet appearances, as Ayo Edebiri, of comedy-drama The Bear, has done with her stylist, Danielle Goldberg. Social media influencers may employ the services of a stylist. And there was a time when men were merely suited and sent on their way, but a new generation of rakish male celebrities, including Timothée Chalamet and Colman Domingo, require as much preparation as their female counterparts. Stylists themselves have become famous as well; for instance, Law Roach, who works with Zendaya, can now make brand deals for himself. View this post on Instagram A post shared by MICHAEL FISHER (@mjonf) Despite all this pressure, several stylists stress that their work often lacks dramatic fireworks. Instead, it requires meticulous planning and an almost militarised approach to organisation. Take Fisher, who estimates he has dressed Stan in almost 100 outfits over the past year as the actor has done press for both The Apprentice and A Different Man. The stylist put outfits together in “chunks”, he says, meaning he will try to call in clothing and create looks in batches that can then be used for a few weeks of appearances. “Depending on the team surrounding the talent, you can get this well-oiled machine and plot it all out,” Fisher says. All of which is no small feat. He has a studio in New York with two full-time assistants, plus a space in LA with freelance help, and says he likes to overcompensate in his “pulls” – meaning he will request more clothing from brands than is necessary, so he can provide plentiful options to his clients. View this post on Instagram A post shared by MICHAEL FISHER (@mjonf) Those outfits must all then be sent back to the labels. Still, no amount of organisation can save a stylist from the moments of absurdity or stress that the job sometimes requires. “I’ve had people literally lay down on the floor of an SUV to not wrinkle a dress,” Moon says. “Or people use those standing buses now. But those are just tricks of the trade.” “Awards day is always a stressful time,” Fisher says. “You have to pray that everyone is in the same radius. Sometimes you’re lucky, and they all get ready at the same hotel, and you’re just going between floors, but there’s always that one rogue person who wants to get ready at home in Malibu.” Fisher, like other stylists, often employs an additional platoon of assistants, full-time and freelance, on both coasts, who can help during the busier periods. “So then you’re just trying to prioritise everything, running on adrenaline and driving against traffic. “I used to drive myself, but then I was just getting ulcers trying to get cars out of valets.” View this post on Instagram A post shared by MICHAEL FISHER (@mjonf) On paper, stylists are there to dress the client, but at least one notes that they are often tending to emotional baggage as well. “I’ve worked with younger nominees who are newer to the game, and there can just be really high emotions on the day of a big show,” says a stylist who preferred not to be named. “It’s like a wedding. One detail can be thrown off, and they can spin out. “All I can do is try to be a calm presence and overly prepared for any unforeseen disasters.” And when all the awards have been bestowed and the champagne has been sipped, remember the stylists – even those at the top of their game – who are doing the very unglamorous work of returning those designer gowns and preparing for the next event. “The other day I was at the 42nd Street [subway] stop with two suitcases waiting for a train to Brooklyn [in New York],” Moon says with a laugh. “That part never really stops – the picking up, the dropping off. And I have a great team, but it is not glamorous in that sense – in Ubers with garment bags and heavy gowns and at the FedEx [delivery] store every fricking day. It’s an endless cycle.”

Who dresses Zendaya, Sebastian Stan, Jill Biden? Stylists on the pressure ahead of Oscars

.css-1c6uqr6{color:inherit;font-weight:inherit;font-size:inherit;font-family:inherit;line-height:inherit;overflow-wrap:break-word;}A celebrity stylist’s life is high-pressure, especially in awards season, and prone to mishaps – like gluing yourself to a client’s garment

A celebrity stylist’s life is high-pressure, especially in awards season, and prone to mishaps – like gluing yourself to a client’s garment