Tracy Jordan: “So what’s your religion, Liz Lemon?”
Liz: “I pretty much just do whatever Oprah tells me to.”–“30 Rock”
To millions of American women, Oprah Winfrey is a near-deity. Whatever she says goes — with the exception of fashion, which has never really been her strong suit. And yet, Anna Wintour handpicked Winfrey to co-host Tuesday’s annual fashion extravaganza, the Metropolitan Museum of Art’s Costume Institute Gala Benefit.
The ball is one of the top yearly fashion events, and is always co-hosted by Vogue’s editor-in-chief. It reliably draws a crowd of A-listers, most of them wearing equally A-list designers. This year, the Gala’s theme is “American Women: Fashioning a National Identity,” which focuses on early iconic American styles such as the Gibson Girl, the Suffragist, the Bohemian and the Screen Siren.
The gala is a hotbed of cutting-edge fashion, which is hardly Oprah’s optimal arena. She’s one of our biggest stars — but that’s both a figurative and literal term, which makes the red carpet a challenge. Middle America loves her for what she wears while lounging on her talk-show couch, and they love her when she commiserates about her weight struggles. Neither of these plays well with Tuesday’s wealthy, stick-thin crowd.
PHOTOS: OPRAH THROUGH THE YEARS
Does that mean Wintour is setting her up for a fall? Hardly. What Oprah lacks in runway savvy she makes up for in star power, and if there is anyone who should be put forward as the modern iteration of American Women and their National Identity, it’s her.
“Is she a fashion icon? No. Is she a style icon? Yes,” says TV personality and style expert Robert Verdi. “Style is an all-consuming quality. It’s about the way she lives, the way she communicates, the way she engages with people. In style, I think she has superseded most people on the planet.”
“She’s like the Everywoman of fashion,” says designer Isaac Mizrahi, whose lilac dress she wears on the cover of the 10th anniversary issue of her O magazine. “She really does a great job of putting forward this incredible image, in a way that absolutely nobody else does.”
True, because nobody else who’s hosted the gala with Wintour has ever made multiple appearances on worst-dressed lists, something Winfrey managed to do for a good chunk of the ’80s.
She’s never been particularly fashion-forward. Even when she includes clothing in her famed “favorite things” show, her choices favor function over style — Ugg boots, quilted Burberry jackets, Eileen Fisher stretch pants. She generally dresses in muted colors and stretchy fabrics.
When it comes to conquering the red carpet, she has come a long way from her garish outfits in the mid-’80s. In 1986, nominated for an Oscar for her role in “The Color Purple,” she attended a pre-Oscar event in “a $10,000 full-length fox coat dyed purple and a sequined gown showing massive cleavage,” as author Kitty Kelley described it in her new biography of Winfrey.
For the awards ceremony that year, she underestimated her ability to shed necessary pounds and ended up wearing a dress that “took four people laying her on the floor to pull her dress on her, and at the end of the evening they had to scissor it off,” Kelley writes, adding that Oprah herself had looked back on the night with horror: “It was the worst night of my life . . . I sat in that gown all night and I couldn’t breathe. I was afraid the seams were gonna bust.”
It was the opening salvo in a lifelong public battle with her weight, which more than anything seems to have defined her fashion choices.
“I don’t think Oprah uses clothes as a way of drawing attention to herself,” says People’s Revolution p.r. firm owner Kelly Cutrone. “She’s usually very monochromatic and pulled together — she’s better off understated. There are a lot of women who we don’t need to see in a big gown.”
Oprah, currently at a comfortable but hardly size-0 weight, will have to contend with a crowd for which “nothing tastes as good as skinny feels” — the mantra of Kate Moss.
Tellingly, several of Oprah’s most memorable fashion moments came during the brief phases when she seriously slimmed down, starting with her show’s famed 1988 “fat wagon” episode. She devoted an entire hour to her near-70-pound weight loss, stepping out in a tight black turtleneck, jeans and spike-heeled boots. (She also pulled onstage a wagon laden with a plastic bag containing the equivalent amount of fat she’d shed.)
And, of course, there was her 1998 Vogue issue, tied to the release of “Beloved,” for which Wintour demanded to see less of her cover girl. The Vogue honcho recently told “60 Minutes” she personally asked Winfrey to lose 20 pounds: “I went to Chicago to visit Oprah. I said simply that you might feel more comfortable. She was a trouper!”
Her hard work paid off. “When she went on the cover of Vogue, it was this moment where she achieved a glamour-icon kind of stature,” says Mizrahi. “She reached a pinnacle.”
The pounds came back on, though.
“I don’t think she’s thin right now,” says Mizrahi, “but she’s not fat, either. She’s in a good place. Honestly, I don’t think she was meant to be that thin.”
Plus, adds Cutrone, “she has to come up with an outfit every fricking day. I don’t think she ever tried to be a fashion player — she just works her ass off. She’s probably like, ‘Just get me a maroon top and maroon skirt.’”
In addition to surrounding herself with the best wardrobe advisers in the business, Oprah also employs a small army of hair and makeup people. As reported in Kelley’s book, Winfrey sports $500 mink false eyelashes. And, as one guest told the author, “Oprah without hair and makeup is a pretty scary sight. But once her prep people do their magic, she becomes super glam.”
Occasionally, she’ll step out in fire-engine red, as with her ruched gown at the 2008 Emmys and the flattering Vera Wang dress she wore to the 2005 Legends ball. Oprah instructed guests at the latter to wear either black or white, then arrived in scarlet Wang, “so that everyone would look only at her,” Kelley reported.
“That was fantastic,” Verdi says. “That, to me, is her coming into her own and totally feeling confident. Red works for her.”
Ultimately, Oprah will rock the Costume Institute gala on the merits of her style — not her fashion sense. “Fashion is a voice before you open your mouth,” Verdi says. “There’s no open dialogue with most celebrities — they’re assessed by what they wear, because they don’t connect with us. But Oprah does, so we’re not judging her exclusively by what she’s wearing. It’s secondary.
“I think she’s an A-plus in life, and a B in fashion.”