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LOS ANGELES — Who will wear what?

Now that the Hollywood awards season has entered full tilt with the SAG Awards and Golden Globes nominations unveiled this week, that is the question that has sent designers, stylists and publicists into overdrive mode, even as the holiday season approaches. After all, the Globes are on Jan. 11 — a mere four weeks away.

This story first appeared in the December 12, 2014 issue of WWD. Subscribe Today.

While the curtain is pulled back ever further on the inner workings of both Seventh Avenue and Tinseltown (sometimes too far, in the case of Sony Pictures’ recent Internet hack), there remains a disconnect between what viewers munching popcorn in front of their living-room TV screens and fashion insiders see as the golden ticket. The former may swoon over a strapless princess gown while the latter applaud more avant-garde choices, but, in either case, the shows and the images they generate equal hundreds of millions of dollars in revenue for television networks, photo agencies and fashion houses alike.

As the linchpins in the process, celebrity stylists face ever-growing pressure from not only the biggest fashion companies but also the most powerful movie studios to help produce the images that can further help propel a film’s box office — and launch an actor’s endorsement deals.

Leslie Fremar, who is working with SAG and Globes Best Lead Actress nominees Reese Witherspoon and Julianne Moore, likens dressing them for the big day to a maid of honor helping the bride choose her wedding dress. “Knowing them both for years and having real friendships with them makes the situation easier, first and foremost. There’s so much trial and error and history, so you know what works and what doesn’t, even though you’re still trying to keep it fresh and new. She knows what she wants to articulate, what she wants to hide, and this knowledge is power.” Fremar also pointed out that confidence and commitment to a custom gown is key. “Like a wedding, you don’t wake up that morning and go, ‘I feel like wearing something else,’ so you have to love what you’ve chosen.” We’ve seen what happens when actresses make last-minute choices (read: Anne Hathaway choosing Prada over Valentino at the 2013 Oscars).

Fremar’s relationship with Witherspoon enabled her to push the actress past her comfort zone of colorful strapless, A-line dresses. Witherspoon, whose red-carpet season started with the premiere of “Wild” at the Toronto International Film Festival, sported a variety of different day and cocktail looks in Toronto, from a purple lace Dolce & Gabbana mini to flowy red Stella McCartney. Fremar pushed her to wear a black Saint Laurent gown to the “Wild” premiere. “She said, ‘I’m Southern. I don’t wear all black,’ but I said, ‘Just this once. It will make an impact,’ ” Fremar recounted. While she said she’s still in “decision-making mode this week” on the dress, “by next week we’ll know what’s going on. The timing is horrendous with Globes the week after the holiday break, but I’ll be thinking about it on Christmas, even though I know I won’t be able to get anyone on the phone.”

With Moore, Fremar gets to live out her ultimate stylist vision, which is why Moore tends to be a favorite among fashion insiders and sometimes misunderstood in the mainstream. “We have similar personal aesthetics, so I push her further. It’s almost like my fantasy of what I’d wear if I had the energy to get dressed. Reese and I have completely opposite personal styles, but I appreciate her for knowing who she is and what works on her. I put a slight push on her — it’s just more subtle. Julianne is more larger-than-life.”

Karla Welch, who is dressing Best Actress nominees Felicity Jones and Amy Poehler, thinks the “Hollywood plays it safe” mantra is a bit outdated. “I don’t think Hollywood plays it safe. I think that is a bit of a sound-bite generalization that gets thrown at us yearly. I expect beautiful tailoring, very modern chic looks out there on all these incredible women,” she said, adding, “I don’t want to give away my dream look because I hope to make it come true.”

While all eyes will be on Jones as the breakout ingénue of the year, Welch said, “Felicity and I have been working together for almost two years, and we love the process [of choosing clothes] and intellectualizing what we are doing, and of course, we love a beautiful dress. Her talent is phenomenal, and she is a beautiful woman, and now we are going to have fun on all the carpets.”

Tara Swennen, who has dressed SAG nominee (and past winner) Julie Bowen for nine years, also counts herself as lucky to have clients willing to push the limits.

“I love being able to play a little, but I warn them every time when they take risks. I might say, ‘That yellow is amazing on you, but some people are going to say you look like Big Bird.’ So, we try and make them calculated risks.” With Bowen, who tends to love simple, drapey or form-fitting columns by designers like Carolina Herrera, she cut a deal. “Julie, if she could, would wear pants to everything. We have done eight or nine years of awards shows, so now we just try and do things we haven’t done yet. I let her wear a comfortable Peter Som to the Emmys but told her, ‘You have to wear this bigger, beaded dress to the Globes because it’s beautiful on you and it’s a departure. So, we’ve had that dress just waiting for four months.”

Swennen is also fortunate in that she won’t be scrambling for one client at the last minute, though, like most stylists, she’s multitasking. Her other client, Kaley Cuoco-Sweeting, who will be attending the shows in support of her nominated cast mates in “The Big Bang Theory,” also has a movie premiering that week. Stylist Petra Flannery, who’s dressing both Jennifer Aniston and Emma Stone, is dressing Gwen Stefani for “The Voice” this week, too.

Longtime stylist Elizabeth Stewart’s roster always includes multiple Best Actress nominees. This year, she’s got Julia Roberts, Jessica Chastain and Viola Davis, so planning as far in advance as possible is key. “For a typical award season, we will have a fitting in the beginning and try to map it all out. That way, we can change things, but there is a plan in place. There are a lot of designer ‘exclusives,’ so it all has to be planned to a certain degree,” she said. While some of her nominees this year appear to be free agents, others, like Jennifer Lawrence, are tied to brands such as Dior.

Roberts has worn dresses as diverse as a short beaded Elie Saab couture suit to the Emmys and a vintage Valentino gown to the Oscars. Stewart said, “Julia is very true to her style and wears whatever she wants with extreme confidence. She’s a stylist’s dream,” adding, “And now she’s a supermodel on top of a nominated actress, with her Givenchy campaign.” That is likely one of the aforementioned designer “exclusives.”

The men’s game is also heating up. Jeanne Yang, who for years has been dressing Best Lead Actor nominee Michael Keaton (he scored both SAG and Golden Globe nods this week), is fortunate to have both a sample-size star (he’s 5 feet 11 inches with a 32-34” waist and a 48-52” suit size) and one with a great sense of personal style. “What’s amazing is when you have the opportunity to go into the closet of someone who’s had a storied career and who knows his stuff,” she said. “He knows the difference between a spread and a pointed collar, the advantage of a roped shoulder, the subtle nuance in fabrics. We speak each other’s language, and that makes working with him both a collaboration and a pleasure.”

Yang sees the myriad of options now available for men, plus the greater acceptance of new colors and styles and an overall fashion awareness, playing directly into Keaton’s strengths.

“He personally likes Ralph Lauren because he has a classic style, yet, at the same time, he’ll go for something fun from Gucci. He loves to put a Zegna shirt with a Ralph jacket and a James Perse sweater. It’s a good sign that it’s not a head-to-toe designer thing.” She pointed to Stefano Pilati’s use of unconventional fabrics and non-matching jackets and pants at Zegna and Dolce & Gabbana’s pairing pinstripes with silk brocade. “The way they are splitting the lapels and mixing fabrics shows how creative designers can get within the men’s wear parameters,” she said.

Keaton’s career trajectory and generation mirror that of men in far more conventional jobs, too. “When the economy tanked, a lot of older guys had to pick up their game and appear cooler and younger. The pleated khaki those middle-management types wore didn’t cut it anymore. Now, anything less than a tailored trouser is unacceptable. With guys over 40, it’s still important they look cool without looking as if they’re trying too hard. But they’re also competing with 20- and 30-year-olds who are getting a cool suit from Topman, tailored and looking amazing.”

That’s the equivalent of competing with Ryan Gosling, Robert Pattinson and Douglas Booth in Hollywood — not to mention fellow Best Actor nominees Eddie Redmayne and Benedict Cumberbatch, both of whom eschew stylists and work directly with brands such as Burberry and Gucci.

Annie Psaltiras, who’s dressing Best Actor nominee Jim Parsons, said, “I think guys are a little bit luckier in that they’re scrutinized a lot less, so they have a lot more freedom to try something different and new. And when it works, they get more attention.”

Think this year’s Oscar winners Jared Leto and Matthew McConaughey in their white jackets — Leto’s by Saint Laurent and McConaughey’s by Dolce & Gabbana.

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