Hollywood Stylists on Developing Award-Winning Red Carpet Style Strategies for Stars

Photographed by Ruven Afanador
Jeanne Yang, Ilaria Urbinati, Law Roach, Tara Swennen and Jason Bolden (from left to right) share behind-the-scenes insights from this year's awards season.

Stylists for Ava DuVernay, Zendaya, Allison Janney and more reveal how they get their clients to listen to them — and what happens when you have less than 48 hours to come up with an entire red carpet look.

How do you develop a comprehensive style strategy for a star client when a boyfriend’s skeptical look could change everything an hour before the red carpet? At THR’s first-ever Stylist Roundtable, Jeanne Yang, who created Kumail Nanjiani’s Oscars look; Jason Bolden, the man behind director Ava DuVernay’s iconic style; Tara Swennen, who curated this season's looks for I, Tonya's Allison Janney; Armie Hammer-stylist Ilaria Urbinati; and Law Roach, who’s responsible for transforming Mudbound's Mary J. Blige from soul diva to shining actress, shared how they approach awards season.

"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," said Roach, who’s also a judge on America’s Next Top Model. It took some time for Blige to fully trust her stylist: Roach had to "talk her into" wearing a mint green Elie Saab dress for the Palm Springs Film Festival awards gala. But the compliments confirmed his choice. "That was my breakthrough point… She said, ‘You’re right. From now on I will listen.'"

Bolden, on the other hand, didn’t quite have the time for much debate: His client Taraji P. Henson wasn’t set on attending the Oscars until two days before the show. "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," said Bolden, who is a regular contributor to E! Live From the Red Carpet.

Things worked out and Henson looked stunning in her custom Vera Wang gown — but there’s more that can cause a last-minute stir up than a spontaneous RSVP. "90 percent of what we deal with are external factors — the manager, agent, boyfriend or designer," said Jeanne Yang, who has worked with Jamie Dornan, Michael Keaton, and Keanu Reeves. "You are juggling 20 balls, and then someone will throw in another one."

For Swennen and her client Janney, "It was about developing a trusting relationship and pushing her a little bit at every single event," the stylist said. "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."

Can a red carpet style strategy make a difference when it comes to campaigning for the Oscar, which Janney won in the best supporting actress category? "I'm sure it affects it," said Swennen. "It's attention. It was beautiful to watch her bloom."