From left: Jeanne Yang, Ilaria Urbinati, Law Roach, Tara Swennen and Jason Bolden. On Yang: Pallas coat, Chloe shirt, Saint Laurent pants, Hoorsenbuhs earrings. On Urbinati: COS sweater, Derek Lam 10 Crosby skirt, Casadei boots. On Roach: Saint Laurent jacket, Dolce & Gabbana shirt and pants, Calvin Klein vest, Gucci glasses, John Hardy bracelet. On Swennen: Adrianna Papell jumpsuit. On Bolden: Hermes shirt and pants, Balenciaga hat. 
From left: Jeanne Yang, Ilaria Urbinati, Law Roach, Tara Swennen and Jason Bolden. On Yang: Pallas coat, Chloe shirt, Saint Laurent pants, Hoorsenbuhs earrings. On Urbinati: COS sweater, Derek Lam 10 Crosby skirt, Casadei boots. On Roach: Saint Laurent jacket, Dolce & Gabbana shirt and pants, Calvin Klein vest, Gucci glasses, John Hardy bracelet. On Swennen: Adrianna Papell jumpsuit. On Bolden: Hermes shirt and pants, Balenciaga hat.
Photographed by Ruven Afanador

Stylist Roundtable: 5 Top Image Gurus on the "Battle of the Black Dress" and Losing Money During Awards Season

The Hollywood Reporter's first Stylist Roundtable features candid confessions from the tastemakers who make the stars such as Zendaya, Kristen Stewart and Armie Hammer stand out on the red carpet: "You don't get on the best-dressed list overnight."

If ever there was an awards season that tested the mettle of Hollywood stylists, it was this one. When Time's Up orchestrated a red carpet "blackout" before the Golden Globes, stylists had just days to find all-black options, as everyone from show producers to nominated talent struggled with what was fashion-appropriate for the politicized mood. One of the upsides of Hollywood's gender-equality reckoning has been the beginnings of a serious discussion about inclusion.

In that spirit, THR hosted its first Stylist Roundtable to discuss how the red carpet itself is becoming more inclusive, among other topics. The guests March 6 were Jason Bolden, 35, who helped director Ava DuVernay become her own style icon; Law Roach, 39, who transformed Mudbound's Mary J. Blige from music diva to leading lady; Tara Swennen, 38, who guided I, Tonya best supporting actress Allison Janney to become a style star; and Ilaria Urbinati, 38, and Jeanne Yang, 50, who pushed the envelope with Armie Hammer (Call Me by Your Name) and Kumail Nanjiani (The Big Sick). Their conversation touched on everything from how the carpet became a #MeToo platform to what stylists get paid (it's not as much as you think).

Who was the first client you got paid to style?

JASON BOLDEN Gabrielle Union.

TARA SWENNEN Lindsay Lohan a million years ago — she had a Proactiv commercial.

ILARIA URBINATI Brendan Fraser. It all went wrong, but I learned a lot.

JEANNE YANG Keanu Reeves. I did the entire cast of The Matrix, actually. It was kind of the beginning of real celebrity styling, which didn't exist. It was a two-month press tour.

LAW ROACH The R&B singer K. Michelle.

What's the biggest misconception about what you do?

SWENNEN [That we] just shop.

URBINATI Thinking we just show up and put clothes on people, that we snap our fingers and there are our favorite looks. They don't understand the item you see go down the runway is the only one in the world.

BOLDEN And it's circulating …

URBINATI … at trunk shows, to editorial shoots at Vogue or Elle. It really has almost nothing to do with what dress you think is best. The dress has to be available at the time you need it, the fashion house has to want to lend it to that particular client, then it has to come, it has to fit, and they have to like it.

And it's always a sample size?

BOLDEN You're lucky if it's a 2.

URBINATI Men's is so much easier. A lot of the time, I'm pulling from store merchandise, and they have all the sizes.

Did Time's Up make this a difficult season, especially the all-black looks on the Golden Globes red carpet?

URBINATI It was more pressure, and there were more things to consider than just what's the prettiest dress.

BOLDEN More like: Could you get another black dress?!

SWENNEN We were all in panic mode.

YANG We were all on text chains.

BOLDEN It was the first time everyone banded together.

URBINATI I had a custom tux made for one of my clients for the BAFTA Awards that we couldn't end up using because we had to do black at the last minute. For the BAFTAs, they made an announcement. But with the Globes, I had publicists calling me, "Are the men wearing black? Do you have to wear a black tux shirt?"

SWENNEN It was a decision that was made very late in the game. Allison Janney's Mario Dice dress had a little white beading, and she was very fearful. In the end, I said that I didn't want that to impede our creativity. So we did it, and it was one thing that set her apart at the Globes.

BOLDEN My client Ava DuVernay said she heard no makeup, no jewelry. Then I looked at her and said, "We're wearing makeup and jewelry." It boiled down to the battle of the best black dress.

ROACH It became fun to see the carpet and how we all interpreted black.

YANG If you think about it, though, there's no other industry where we can push an agenda like this. The fact is that artists, whether in music or film, have always been the progressive front because we have been the most accepting of being different. It's wonderful that the red carpet [is] more important than just what you're wearing.

How do you develop an awards-season style strategy for a client?

ROACH I try to figure out who my client is and not change them but just elevate if I can, so it's a lot of them and a little bit of me.

Let's talk about Mary J. Blige.

ROACH My mind-set was to introduce the world to Mary the actress because we're so familiar with Mary the singer. But when I met her, I was schooled. She said, "I like what I like." I had to figure out clever ways to introduce things that were still her — but she didn't know were her yet. What people don't understand about this job is that it's not about the dress. It's about the psychology of what leads up to the dress. Every time we'd [try on a dress] and pull the shoulders down, her posture would change. So I figured out, this is her comfort zone. After that, everything became off-the-shoulder.

Did you have to talk her into things?

ROACH I had to talk her into wearing the mint green Elie Saab for the Palm Springs Film Festival awards gala because that was a color and silhouette she had never done. That was my breakthrough point. I finally just said, "Trust me." She did, and the reviews and compliments she got. … She said, "You're right. From now on I will listen."

Tara, how did you work with Allison?

SWENNEN It was about developing a trusting relationship and pushing her a little bit at every single event. For the I, Tonya press run, we did something like 55 outfits by the end. We didn't want to repeat too many colors or patterns or shapes. She also is over 6 feet tall, and we could play with her because she is a fashion stylist's muse. If you look, she was getting progressively a little bolder.

Do you think a style strategy can make a difference when it comes to an Oscar campaign?

SWENNEN I'm sure it affects it. It's attention. It was beautiful to watch her bloom.

How do you feel about criticism?

BOLDEN Everyone has their point of view. But I tell people, "Do you really understand what just happened?" She could have had the most amazing dress five seconds ago … then she was late, she drank last night and can't fit in it.

People don't realize all the things that can go wrong.

BOLDEN Or that you get last-minute phone calls that a client is just deciding to attend.

You were saying that your client Taraji P. Henson was a last-minute RSVP to the Oscars!

BOLDEN [I had] two days. She is the nicest human on the planet. She shows up to fittings, puts it on, and if she starts talking to herself in the mirror, it's done: "Oh, this is a queen moment, honey! The bitches are going to lay at my feet, honey!" Then she starts doing her posing.

YANG It's interesting there's never been a styling competition reality show because 90 percent of what we deal with are external factors — the manager, agent, boyfriend or designer. You are juggling 20 balls, and then someone will throw in another one.

SWENNEN People forget a lot of designers don't want to dress your clients. I remember with Kristen Stewart, I called Lanvin for seven years. They said, "Listen, our demo to sell these clothes is closer to the 30s, so she's not what we want quite yet." Every two months, I called and said, "Are we ready yet?" Finally, it was like the clouds opened up, and we got it, and she was like, "Nah."

By then, she was under contract at Chanel.

BOLDEN If you say no to me at the beginning, no is forever. I am notorious for using the exact same email that says, "Unfortunately, we would like to pass." So I go back and write, "Unfortunately, WE'D like to pass!"

ROACH I do the same thing!

BOLDEN I don't really know if it's the design houses more than the PR people. Because you have these girls and guys who sit there and just because that is not something they [themselves] watch on television, it's not important.

URBINATI It is funny how personal it is. You'll have someone random on some show, and you think they'd never loan to you, and the designer turns out to be a huge fan. I have worked in every aspect of the business, so I understand as a brand you have a certain image. If you are Gucci and you have five runway-worthy dresses that season, maybe you want to save them for the big moment.

Do you think there is enough inclusion in terms of whom fashion brands are willing to loan to?

ROACH I built my career and Zendaya's career on not using any big brands at all.

BOLDEN Boom.

ROACH I will tell you why, because in the beginning they wouldn't touch her.

BOLDEN Pass, pass, pass.

ROACH Zendaya made it to the cover of Vogue, she has never worn Valentino, Gucci or Chanel. She only wore Dolce & Gabbana when she got a Dolce campaign. We built that girl's career and my career using smaller brands and emerging designers to prove a point. Now that they want to dress her, I say no. We go to Paris, you see the designers, they say, "I love her, how come I've never dressed her?"

YANG You have to build relationships though, that's what I tell my clients: Go to the lunch, go the event. I'm the OG of the group. There are designers I have worked with for years who once in a while will say no. It doesn't matter if I have the biggest A-list star in the world, it's not a match. It's a testament to you that you're able to work around it.

SWENNEN For devil's advocate, now people are doing street style, so those samples could all be going to the airport on a Jenner and it's game over. There are more people in Hollywood and the music business than ever … everything is spread super thin.

If it's so hard to borrow, why not just buy?

YANG Actors don't have tons of money, at least in the beginning, so it's about buying some and borrowing some, getting smart pieces and developing their style. When I started working with Kumail right before the Emmys, he was hoping to get his movie to Sundance. Cut to Oscars. But even still, you don't get on the best dressed list overnight. One thing I want to convey to young actors is to develop a trust in us, let us go in for a long game, don't have us just for a few red carpet events.

But a great Gucci dress, why not buy it?

URBINATI Then anybody can wear it, and they do "Who wore it best?"

ROACH In the beginning, I only put Zendaya in things other people have worn because literally she is 6 feet tall. Who is going to wear it better? She is.

Do you think men get more of a pass on the red carpet?

URBINATI Men dressed really boring for years, then my client Armie [Hammer] wore a red velvet tux to the Oscars in March. Men are getting praise because they are finally wearing color, doing something different, whereas when women take risks, they get eviscerated. That has to stop. I think it's crazy we're doing this whole Time's Up thing and talking about the way we treat women versus men, but somehow no one is talking about how it's OK we tear women to shreds in the media. There were a couple of people who didn't wear black to the Globes, and people were shaming them on social media. Maybe that person felt like wearing red made more of a statement, maybe she didn't get the memo.

SWENNEN I always say you haven't made it until you've made it on the worst dressed list.

YANG People have said stylists have ruined the red carpet. I feel like for the first time, we see people of all sizes, colors and shapes, and you can identify and say, "Oh, that person, I love her city style or his ability to peacock." That to me is what makes it.

Jason, Ava is a director, someone behind the scenes, who has now become a style icon.

ROACH Can I say, I'm obsessed with what you do with her. I love when someone creates a point of view for a client.

BOLDEN Ava is a force, the voice of now. Ava is not the normal size we are maybe used to seeing. She wears The Row to Prada, and it's all custom. The people who buy The Row do not look like those girls [designers Mary-Kate and Ashley Olsen]. That consumer looks like Ava. When you think about the dollars and cents, what's keeping these businesses afloat, it's someone who looks the opposite of that PR person [or designer], and [they] are saying no to that person. So, it goes deep.

What is it like working with a designer on a custom piece?

BOLDEN I'm straight up sketching. When I was working on Yara [Shahidi]'s 2017 Emmys dress, I was on the phone with [Prada] saying it had to be her last princess moment.

URBINATI Even with Armie's red velvet Armani tux, down to every button, the lining, the lapels. When we decided on the red velvet, I said if we put a black lapel on it, which you normally do on a tux, it will look like Hugh Hefner or a weird vampire. All those little details are the difference between what makes it work and what makes it ridiculous.

Some people think stylists get paid under the table by designers to dress their clients.

YANG When a makeup artist or a hairstylist comes to a shoot, they are paid their full-day rate. When we go in for the awards shows, we typically get paid [by studios] about $1,000 per look. Then we deduct our expenses: shipping costs, paying assistants and tailoring, and it costs up to $1,500 to $2,000 per look.

So during awards season, you lose money?

BOLDEN Every day.

SWENNEN We have no union to protect us, and the studios have banded together for a set rate that's not enough. You can get into an uncomfortable position with your client, who will say, "I'm promoting this movie, why should I pay for my own alterations?"

URBINATI If it's worn on the red carpet, designers will usually cover tailoring.

SWENNEN The aesthetic is key, so we're not going to compromise your look just to get a little side cash. That being said, we will openly welcome it if it's available.

ROACH It's not like you're striking a deal. The brands will pay your day rate. I went from making $10,000 a day working with girls in music who didn't have the right look to making $750 a day for someone Hollywood thought had the look. We take these jobs, make less money, put ourselves in the hole, so we can make it to that magazine.

URBINATI It's a long game, the equivalent of an actor doing an indie movie.

SWENNEN But it's worth the money to ensure we do our job properly, and the lead actress or actor is looking …

BOLDEN … like a movie star.

This story first appeared in the March 21 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.

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