I Asked 3 Red Carpet Stylists What It’s Really Like to Dress Celebs

Tilda Swinton

After years of styling people for Man Repeller photo shoots, I’ve become somewhat familiar with the unique varietal of intimacy that is dressing another adult human. More often than not, it involves wearing the hat of “amateur therapist” in addition to that of “stylist,” and navigating the complex cocktail of emotions, vulnerability, and identity-parsing that can arise from the simple but powerful act of putting on clothes. It is for this reason that I am deathly curious about what it’s like to be a celebrity stylist. Because imagine how much higher the stakes are when you’re engaging in this delicate dance with Reese Witherspoon. Or Viola Davis. Or Meryl Streep. I’m stressed just thinking about it!!! But I’m also fascinated and dying to know everything.

My sense of curiosity is particularly heightened during awards season, when the inundation of red carpet attire exacerbates my desire to glean all the juicy details behind how each look was chosen. Was there drama? Intrigue? Competition? A last-minute change? I HUNGER FOR THIS INFO. With the Academy Awards on this weekend’s imminent horizon, I decided to enlighten myself–and you, if you happen to share my zeal. Below, three celebrity stylists* myth-bust some of the most fun rumors I’ve heard about the business of dressing famous people.

*Names have been changed.

TRUE or FALSE: Everyone wears Spanx.

Gwyneth Paltrow  at the 77th Annual Golden Globe Award; January 05, 2020

Lillian: False. If they don’t need them, there’s no reason for them to wear them. I have a personal hatred for what I call “sports bra ass”–you know, like a tube of ass–which is the effect Spanx often conjures. It’s compacted, and it’s not sexy. Also, if you’re hoping to hook up at an after party, you don’t really want someone to touch your body when you’re wearing Spanx. It has that sausage feeling.

Billy: As far as women are concerned, I would say that’s true. You need every possible advantage when you step out on the red carpet. When you’re shooting a celebrity for a magazine, all you need is one good picture. When you’re on a red carpet, all a photographer needs is one bad picture of that person for it to go viral. Anything you can do to mitigate anything that makes the client insecure is an absolute must. I actually remember one particular Oscars night when I was getting an Academy Award winner dressed for the Vanity Fair party–she wanted to stay in her Spanx but had to wear a dress with a split that went up to her upper thigh, basically her hip bone. While she was standing there surrounded by friends and family and everyone who had been there with her through her long and very storied career, I was down on my hands and knees with a pair of scissors pressed against her thigh cutting a V-shape into her Spanx so they wouldn’t be visible on the red carpet. It was the most nerve-wracking moment of my life.

Natalie: False. They’re so uncomfortable and sometimes actually hurt the look by adding bulk more than help. As an alternative, I’ve had corsets made for my clients that are built into the dress. I also use a lot of adhesives, thongs, pasties, etc.

TRUE or FALSE: There’s A LOT of drama involved in working so closely with famous people.

Lillian: That depends on the person. With some people, there’s a lot of drama. Certain people who are actually cursed. Their zipper will break, their heel will break, their bra will somehow magically turn into the wrong size. And then with other people, you can pack them a bag full of shit and they’ll look great no matter what. 

Billy: It depends. By and large, most celebrities are very pleasant to work with, it’s the people they surround themselves with who are a source of a lot of heartache and drama. As a celebrity, you get to be nice by employing an agent and manager and publicist who are evil and terrifying to be around. That affords the actor or singer or whomever a great deal of latitude to be more carefree and down-to-earth. Behind the scenes, dealing with talent publicists is easily the worst part of the job. You have to bite your tongue and take whatever comes your way. I don’t really do much celebrity styling anymore, and part of the reason is because the prevailing emotion that permeates every day of your life is desperation. It doesn’t matter how important your clients are, you are just one disaster away from losing it all. Often, those disasters are foisted upon you by circumstances that are completely out of your control. You may work with an Academy Award-winning actress that every brand will dress, but your relationship with that actress is only as good as your relationship with her publicist. That publicist decides who hires you and if you come back for the next awards season, and that publicist might have 20 or 30 other clients who pay [your] bills. So you’re not just dressing Academy Award winners, you’re dressing the publicist’s B- and C-level clients that designers have no interest in. You have to find them looks in order to stay in the publicist’s good graces, and that’s the dance of celebrity styling. At any given time, there are probably only 200 or 300 celebrities that designers really care about dressing, and the rest of them are incidental. You have to find a way to satisfy those “less important” clients, or you’re not going to get the more important ones.

Natalie: True and false. Depends on the celeb! Everyone has a different personality and a different way of working. Some are way more difficult than others. I keep my cool by trying to be as easy and accommodating as possible. That’s part of the job–being ready and down for everything. And I mean anything. Some people want you to wait for them.. and wait… sometimes all day long. Others are quick and thoughtful about your time. I’ve been on set for 24 hours straight waiting for a client to do a fitting.

TRUE or FALSE: You have to compete with other stylists for the most coveted pieces.

Jodie Turner-Smith at the Academy Of Motion Picture Arts And Sciences’ 11th Annual Governors Awards; October 27, 2019

Lillian: It depends. I’ll usually send requests to hold certain pieces right after a runway show, like, “I want these looks for the season. Please don’t give them away to anybody else,” or, “Listen, so-and-so wants to wear this and the event isn’t for three months, don’t give it away to someone else before.” With award season, though, a lot of stylists ask for exclusives. They’ll say, “Okay, my client is going to wear Givenchy to the Golden Globes, nobody else can be wearing Givenchy,” and the designer will grant that and then nobody else can call the brand in. But I don’t do that. I don’t get it. I don’t understand what it signifies other than a power trip. I think PR people like it because it means they’ll have less work trafficking all the samples. 

Billy: It’s certainly true that competition for the season’s best samples is stiff; that said, I think it’s pretty rare that stylists are feuding amongst each other for the best pieces, especially during award season. Stylists often commission custom gowns for major events, and top-tier designers typically supplement these offerings with capsules of evening-wear specifically made for the red carpet. I can recall a handful of incidents in which a stylist-to-stylist feud broke out over these samples, but it’s rare. The truth is, stylists are not really at war with each other—they’re collectively locked in a nonstop war of attrition with fashion publicists. These publicists are the ones who control the flow of product, and 48 weeks out of the year they are sadistically withholding. (Major red carpet events like award shows and film festivals are the rare exception to this otherwise ironclad rule.) The reason is simple: Despite their waning influence, magazines are voracious hoarders of product, and they exert an inordinate influence over fashion publicity firms. Ask any red carpet stylist where the good samples are hiding and they will complain to you bitterly about the 50 or so racks of clothing gathering dust in the hallways of Vogue.

Natalie: True. But the celebrity is normally the selling point. The more interested the brand is in dressing a certain girl, the more keen they are to send the dress to her. I send out requests as soon as I know my client has an event coming up.

TRUE or FALSE: You have to travel with your clients to award shows to hold their trains/steam the outfit again before getting out of the car.

Lillian: False. I don’t do that. I mean, you’re talking about 10 minutes in a car, what the hell is going to happen? Also, I couldn’t get credentials to go to the Oscars. They’re highly secure. Even the most famous celebrities have to take their ID with them. You can be nominated for an Oscar and still have to have your driver’s license or your passport in your bag.

Billy: I’d say that’s by and large false. I’ve only been to a premiere or show that my client was attending like five times in my whole career. There are outliers, though. For instance, some dresses are so large they don’t fit in the car, or so delicate they will immediately wrinkle—for example, that Dries van Noten dress Maggie Gyllenhaal wore to the Academy Awards in 2010 was beautiful, but all you saw was the wrinkles. In cases like these, you have to bring in a sprinter van and the actress will stand the entire way to the show. Once the dress is on, there’s not much you can do to re-steam it. You want to keep a steamer as far away from human flesh as possible. It’s like an iron, you can really hurt someone (I’ve heard horror stories). One awards season, I was working with a super high-profile male client who brought his mother to the Academy Awards as his date. Everything was perfect, her dress fit her well, we had a little trouble getting her zipped in, but she looked like a million bucks. We got her in the car and my colleague and I were high-fiving because we weren’t going to see them again for the rest of the night. Five minutes later, I hear a blood-curdling scream. The zipper on this $10,000 Prada gown had split when she sat down in the car. Luckily we had a backup dress. You always have to have a backup. Not only for the dress, but for everything. At the first event that I ever got someone ready for, I sent the girl off to the event at the Beverly Hilton, went home, opened a beer with my friends, and right then, I got a call. She was like, “The heel snapped on her shoe, how fast can you get back here?” I jumped in my car and I was there in 30 minutes with three other pairs.

Natalie: False. Only when it’s a big red carpet event. In general I just tell my clients to lay down if they’re riding in a car or get ready as close as possible to the time of the event! On big awards show nights, I allocate my time based on who books me first and who has the budget to pay to have me on set. Sometimes I’ll send an assistant, and sometimes people are okay to get themselves ready alone.

TRUE or FALSE: You don’t sleep during awards season.

Saoirse Ronan attends the EE British Academy Film Awards;  February 02, 2020

Lillian: Somewhat true. I feel anxious, so I don’t sleep. I worry about things. I’m not a great sleeper to begin with, so I spend a lot of time in bed thinking about things. I want the dress to be perfect. What’s going to make it look perfect? What’s going to fuck it up? I turn things over in my head over and over and over again. There are so many things that could fuck up the look–bad jewelry, weird hair, the wrong shoe, the wrong length. That’s what I obsess about.


Billy: That’s false. If you’ve done your job correctly, awards season should actually be one of the easiest times of the year for you. That’s when the designers are clamoring to get their clothes on your client. You’ve had everything plotted out from the moment your client was nominated. You’ve secured the best looks from the season, and anything you couldn’t secure you had custom made. You’ve made arrangements with the jewelers and shoemakers and bag companies. This is when all of the pieces fall together pretty easily if you know what you’re doing. I will say, you can plan as much as you want but life inevitably gets in the way. One awards season, we had commissioned a custom gown from a designer in Paris who is unparalleled in terms of his reputation. He didn’t dress celebrities for decades, and when he decided to dress someone again, it was our client. He told us that he was making something custom for the Academy Awards. For weeks, we were kept in the dark as to what he was making and it wasn’t until ten days before the show that his team sent a sketch at our insistence. Think about everything that you’d want out of a major awards show dress: color, volume, drama, a little bit of classic Hollywood. This was diametrically opposed to all of those things. It was a thick black velvet turtleneck gown. It was very interesting, but not right for our client and certainly not the Academy Awards. One of the hardest calls I’ve ever had to make was to call the designer’s assistant and tell her that she wasn’t going to wear it. It was too late to do a custom dress or pull something through the usual channels, so we had to go to extraordinary lengths to find a replacement.

Natalie: False. I sleep. I just go to bed the second I get off work and wake up and get right to work. I don’t have time or feel the need to go out and celebrate. It’s too exhausting trying to do both.

TRUE or FALSE: You bring your client hundreds of dresses and sometimes they choose none of them.

Lillian: No, I don’t do that. For an award show I provide between 5 and 15 choices and I almost always know before I go into a fitting what’s going to work, but I want to show them other things in case.

Billy: Absolutely true. I don’t know that “hundreds” is accurate, but I’ve definitely had fittings where we have six racks of gowns from top-tier designers and after trying on 50-60 options, the client says, “Where are the rest of them?” I remember one year for the Emmy’s, we worked with a high-profile actress who went on to win that year. She could only do fittings on Saturday mornings, so five weeks before the show we brought 100 dresses to her home and she didn’t like any of them. We went back the Saturday after that and the Saturday after that. We ended up doing four fittings with dresses and she didn’t like any of them. She ended up wearing a dress that she found on the third weekend, but right up to the day of the show, she kept asking me if there was anything else. Finally, her publicist had to intervene and finalize the choice. She was locked in at that point. If you’ve done your job well, you don’t need hundreds of dresses every time. It betrays a sense of fear to your client. If you really know your client, three racks of clothes will get the job done. It’s like walking into the supermarket–you have the world at your feet, and suddenly you have no idea what you want, because there are too many choices. At their absolute best, a stylist is an arbiter of taste. It’s rare that you get to work with a client who fully trusts you on that level, where they don’t expect to see heaven and earth. You have to keep in mind that at the end of the day, it’s really their publicist that you work for. You can love something, your client can love something, but if the publicist doesn’t like it, they have veto power. They have an image of what they want to create. The best-case scenario is that you have a hands-off publicist or a publicist who trusts you. What I’ve found is that most publicists are stifled/wannabe stylists and they vent that frustration by throwing sand in the gears of your tightest operation.

Natalie: Depends on the client. Some want racks of options and some want to be told what to wear. In the beginning of my career I used to bring a ton of options, but now I’m so comfortable with my clients and know their style well enough that I can do a tight edit with the confidence that something will work.

TRUE or FALSE: Styling celebrities is a vehicle for becoming genuine friends with them.

Awkwafina at the 77th Annual Golden Globe Awards; January 05, 2020

That’s a tricky question. I’ve had some clients for over 15 years and to say that we’re not friends would be an insult, but I’ve made the mistake of thinking I was friends with certain designers or celebrities, and then gone on to realize it’s just business to them. In general, I try not to hang out with my clients outside of working together because I think it complicates things. Sometimes a friendship happens naturally, but I prioritize professionalism above all else. I want our dynamic to be really warm, and for them to feel cared for and loved, but I don’t want to hang out with them.

Billy: Absolutely false. Celebrity stylists and definitely stylists of a certain generation are terrified of their clients. “Celebrity” as a profession is one that can take over your entire life and can fill you with such insecurity and emptiness, and the space for friends and family needs to be filled by people without a profit motive. Historically, giving your client the luxury of not feeling obligated to entertain you socially has been the hallmark of a true professional. However, I think that’s starting to change with younger celebrities, especially with celebrities of the Instagram age, like the Kendalls and Kylies and Gigis. They have ushered in a whole class of stylists that don’t necessarily take the same route to the top that old-school fashion stylists have. Nowadays, a lot of people become stylists because they’re already friends with a celebrity.

Natalie: True and false. It’s all based on personality. If you vibe, you vibe, and if you don’t, you don’t!

Photos via Getty Images

Harling Ross

Harling is a writer and was most recently the Brand Director at Man Repeller.

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