"I Don't Want You Coming to Meetings in Yoga Pants": The Executive Stylist Roundtable
Photographed by Diana King

"I Don't Want You Coming to Meetings in Yoga Pants": The Executive Stylist Roundtable

What is appropriate power dressing in the C-suite and on the red carpet? Seven fashion experts debate: "What you wear changes your ability to level up."

Getting dressed for work in Hollywood has come a long way since the "power suit," a term inspired by the look that Giorgio Armani created for Richard Gere in 1980's American Gigolo. "Women were in need of appropriate professional attire akin to that of men, something that would adorn them with a sense of dignity and an attitude that would enable to them to satisfy the demands of professional life without having to give up on being women," Armani tells THR. "I tried to render all that into a strong image, and from there was born the phenomenon of the power suit." The look clinched the designer's dominance among showbiz clientele, along with VIP services that catered to executives such as former Paramount Pictures CEO Sherry Lansing as well as onscreen talent.

While celebrity styling has become a highly visible segment of the fashion industry, executive styling — dressing studio heads, directors, writers and producers — remains on the down low. Many execs get help from retailers' in-house personal shoppers, closet experts, stylists or a combination of all three. “It’s expected for an actress to have a stylist, but an executive might worry that they’ll come off as frivolous and self-absorbed. Styling services are super helpful, even a necessary tool, but they often don't feel a need to talk about it,” says style expert George Kotsiopoulos, who has dressed studio heads, writers and directors in the past.

"Social media has helped normalize the idea of having a stylist," says Kent Belden, owner of The Only Agency, which represents stylists who work with both talent and executives like Endeavor CMO Bozoma Saint John, a client of Negar Ali Kline. Says Ali Kline: "When you put on a jacket that feels really good and the cut is perfect for your body, your posture changes. It gives you that extra bit of confidence — that's a very powerful tool to have." She adds that women in Hollywood can be among "the busiest women on the planet; using a stylist really reduces my clients' cognitive overhead so they don't have to think about" dressing.

The seven stylists convened by THR took different paths to their jobs, starting at magazines (Ali Kline at Paper); fashion brands (Tanya Gill at Jean Paul Gaultier; Meg Chapman and Jordan LaValle at Prada and Lanvin; Stephanie Gisondi-Little at Emanuel Ungaro); or department stores (Andrea Lublin at Nordstrom). One thing these women share is the opinion that executives are, naturally, less dramatic than actors. "No one's dying if something doesn't look right," says Shonda Rhimes' stylist Dana Asher Levine. "We fix it and move on." Here, they discuss how executive dressing has changed in Hollywood and where to find clothes larger than a size 6 in L.A.

How does styling differ for an executive compared with an actor?

NEGAR ALI KLINE The approach is similar. A lot of executives are more forward-facing now. People require more transparency from the companies they support, and in turn executives have to be more engaged with their audience; they understand the need to cultivate an image. With a celebrity doing a press tour, there are certain events we're styling for, similar to an executive's schedule. There may be a constant flow of fittings or one-offs for an awards show. But the process is the same.

MEG CHAPMAN Jordan [LaValle, styling partner] and I worked with [Breaking Bad] writer-director Moira Walley-Beckett, who can be in her writing uniform for a year, but when a project is out, she has to make the same decisions a celebrity does: What is my brand going to be when I do the press junkets or go to the awards shows? So, you create a story that makes sense for them.

JORDAN LAVALLE It's harder taking executives out of their comfort zones. You tread an interesting line in terms of keeping them where they're comfortable and making sure they look appropriate and shine for the event.

Dana, since you're one of the OGs in this industry, do you recall when executives were considered merely "behind the scenes"?

DANA ASHER LEVINE Absolutely. And now they're not. Shonda Rhimes, for example, used to wear pajamas all day because she was at home writing. Now you've got Shonda, Jenji Kohan, Robert and Michelle King, who've become celebrities in their own right — they speak on panels, they're Dove representatives. Shonda, especially, has a very large following, so everywhere she goes, it's like with the Obamas. When all of her four [ABC] shows came together, there were a lot of events for that.

Another longtime client, Dana Walden [chairman of Disney Television Studios and ABC Entertainment], has become more public-facing as her job has become more and more corporate. She now has fittings every week for her constant flow of events.

How does it affect your process when being loaned samples or gifted clothes is not an option?

STEPHANIE GISONDI-LITTLE Let's say they're attending the Grammys or the SAG Awards, but may not be going onstage. [Gisondi-Little styles Better Call Saul producer Ann Cherkis, among others.] You have to be clear about the options. If you want a YSL smoking jacket, that's going to cost X dollars. Generally, for these events for folks not being loaned things, the low end would be $2,000. I try to amortize it for them: How can you wear it again? Hopefully, it gets multiple wearings, [for example,] you separate a Jil Sander suit so that it can take them to multiple events.

Some people are really stuck in that Garanimals way. They can only see things paired a certain way, and you go in with a fresh eye and are able to reinvigorate things and say, "If you tailored this," or "If you changed that hem." I have had people say that they've actually ended up saving money by hiring me.

ALI KLEIN I joke about a CPU, a cost per use, if someone's not so comfortable spending X amount on a pair of trousers. I will guarantee these trousers you will keep in your closet season after season after season.

LAVALLE No one is scared of the investment piece, you can absolutely move that. But not all of our job is personal shopping. A large percentage is going back into the closet and working with pieces that people say, "I love this, I bought it, I have no idea how to wear it." We call them inspiration pieces. So we're actually shopping within the closet.

And I don't know if you guys do this, but we'll go into a closet and say, "Where is your black cardigan? Where is your skinny black pant?" [Nods all around.] Sometimes that's where we'll start our shopping.

TANYA GILL For someone like Jane Fonda, who is both an actress and executive [Grace and Frankie executive producer], we work with couture and custom. [Gill also has worked with Planet of the Apes writer-producer Amanda Silver, former Fox film head Stacey Snider and Sony Pictures' Elizabeth Gabler.]

But I've had young clients who aren't familiar with the process, who sometimes want things that they see on actresses, but obviously, they're not always available because they're samples often made just for the red carpet. Sometimes I've been fortunate that a client is sample size and designers will loan, but otherwise we work with a budget that has to be decided at the beginning of the press campaign.

ASHER LEVINE It's also a progression with someone's career. With Dana, whom I've been working with for more than 20 years, we started with Theory and now we're up to Valentino and Carolina Herrera. We've raised our standards. I bought her a Tahari dress not long ago, and she said, 'It's so cute, but look, this just doesn't fit [because of the cut].' I laughed and said, 'I remember a time when Tahari was a big deal for you!'

When you're shopping for someone's wardrobe, how do you allocate workwear and event clothes?

ANDREA LUBLIN I do mostly personal shopping — my clients range from agents to actresses [including entertainment attorney Jeanne Newman and UTA partner Marissa Devins] — so 95 percent of what is bought is worn over and over. They want stuff that's going to take them to an event but can also be worn for everyday versus one red carpet look. I'd say 90 percent of it goes under office and street style and 10 percent goes under events. People are willing to spend for both if they feel good in it.

GISONDI-LITTLE People often associate styling with, "It's just about shopping and expensive clothes and it's not for me." But there is real data around a social psychology concept called "enclothed cognition," how what you wear changes your comportment. It changes your ability to level up and do your job. Styling is about so much more than just clothes.

What happens between movies or during a hiatus?

ASHER LEVINE When you don't hear from somebody for a few months, you think, "Oh my God, they cheated on me, they got a different stylist." But really, they haven't bought one thing, not even a pair of underwear. I have executives who have movies that come out every four years, like Terminator. And they literally have worn the same clothes for four years. Maybe not the same underwear, but the same clothes.

LUBLIN It's an interesting time. People are needing to care more because everyone is getting photographed more, and everybody is sick of showing up, spending a lot of money and not standing out. This is such a tough society, and to get photographed twice in the same piece, is it OK? It depends, like a black trouser … but I'm not even sure that for this level of people it's OK. There's a lot of pressure. That's where we all can come in and lift them up. I think once it gets to the level where you're hiring somebody, it's not so much about the budget, it's about the experience of putting your trust into somebody and getting results.

How has executive style changed in the past few years?

ASHER LEVINE I like to tell this story about a newer client, whom I got thanks to Rupert Murdoch. He was going around the room in a meeting and said, "You, you and you … call the person who dresses Dana Walden. I don't want you coming to meetings in yoga pants anymore." So I think it's either casual Fridays or … a very fine line. But there are more options today. In the old days, you couldn't show your feminine side because that meant you weren't smart enough or doing your job. Obviously, we've come a long way in that you don't see those black suits as much.

ALI KLINE We don't have to dress like one of the boys. My client Bozoma Saint John always promotes her slogan, "Bring your whole self to work." If you want to wear fringe and sequins and show up to the office, it's perfectly acceptable. She is a unicorn. But it is shaping the conversation. I do believe more women feel empowered to be exactly who they are within the corporate structure.

Do you think there's more leeway if you work in Hollywood and creative fields?

CHAPMAN Absolutely. You have to show that point of view through dressing. So the power suit for a woman could be a Valentino dress with a Saint Laurent jacket. We can do a Gucci blouse with a Celine jacket. It's not the 10-years-ago Prada tailoring that every woman was wearing.

Has the #MeToo movement affected what people wear?

LAVALLE One of our clients, Mariska Hargitay, premiered her documentary about sexual assault, I Am Evidence, at Tribeca right around the blow up of #MeToo. We're always trying to highlight her amazing figure, but I remember for the first time it feeling a little sensitive, and her making a point of wanting to stand in solidarity with the seriousness of the subject.

CHAPMAN Working with an actress like Mariska, who has transitioned to behind-the-scenes producing, directing and writing, we've become less playful and romantic and a bit more serious and powerhouse. She might be meeting with HBO, but she might also be meeting with somebody in Washington, D.C., so we have to create this power through her outfit.

Conversation edited for length and clarity.


Hollywood Black Book: Executive Style Resources

SUITS Veronica Beard, Rag & Bone and Victoria Beckham are preferred by stylist Andrea Lublin, while Dana Walden's stylist Dana Asher Levine likes "Nordstrom's basics because they last and dry clean very well," like its Halogen black pant. Adds Jordan LaValle, part of a styling duo with Meg Chapman: "We love suits from A.L.C. because they have a bit of fashion and go up to a size 18." Stylist Tanya Gill counts Blase ("different, European"), Valentino, Dior and Alexander McQueen among her favorite suiting brands.

NON-SAMPLE SIZES "A lot of boutiques in L.A. don't sell anything bigger than a 6 or an 8," says Lublin, whose go-to's include Net-a-Porter, Matches and Moda Operandi. 11 Honoré does "great designers in larger sizes and are so accommodating," says Asher Levine. Stephanie Gisondi-Little recommends online resource Roucha for sizes larger than 8. Says Gill: "Christian Siriano creates clothes for all different-sized women. I also love Escada for larger sizes, and St. John has wonderful knits that stretch and smooth."

AWARDS SEASON Armarium "is a great resource for renting and buying dresses, red carpet gowns and awards season looks," says Negar Ali Kline.

ALL-AROUND "Women always feel empowered and beautiful in Stella McCartney clothes, and it's a sustainable company, which clients are talking about more," says Gill. For Chapman, "Our go-to resource for women is local Elyse Walker," and she adds that "The Row is very flattering on a lot of different body types."

This story first appeared in the Oct. 9 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.