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Poppy Delevingne, 21, and Chloe Delevingne, 23, London "It girls"
One of the joys of being in your 20s is discovering, but not yet having to commit to, who you are, at least in how you dress. "Some days I wake up and I will want to be rock 'n' roll, and I will fling on some sunny jeans, an AC/DC T-shirt, and a leather jacket with crazy bed hair," Poppy says. "The next day I will feel like being a little princess and wear some floaty summer dress, and beautiful sandals I got at Rondini in St.-Tropez."
Winona Ryder, 35, actress
"I never felt like a physically beautiful girl," Ryder says, "but I've always felt like I was unique, and that mattered way more to me."
Lisa Randall, 45, Harvard theoretical physicist
"It's difficult for women in science," says Randall. "It's a double-edged sword. I don't want to seem frivolous—though obviously I'm not, because I'm a physicist. I think there are a lot of women in physics—and there really aren't that many women in physics—who sort of don't really know how they should dress," she says. "You want to just blend in. On the other hand, you're never going to blend in. The great thing about getting older is you don't have to care."
Robin Brooks, 52, chairman and CEO of Brooks Food Group
At 52, she has gorgeous, unlined skin and a body most 25-year-olds would kill for. But there is a strength and a presence that go well beyond the clothes and the car and the immaculate grooming, beyond the gold-and-diamond Cartier Tank Française watch and the vintage gold Cartier bangles and the pretty pear-shaped topaz held by a thin gold chain at the nape of her neck. Call it glamorous gravitas, and it attracts not just attention but respect.
Mary Heilmann, 67, artist
A feisty, white-haired woman whose forthright manner is punctuated by frequent bursts of infectious laughter, Heilmann seems entirely comfortable in her house, her life, and her work. At the age of 67, she is having her first museum retrospective at the Orange County Museum, and Heilmann's status as an artist's artist, for whom public recognition has always been just around the corner, is certain to change.
Vanessa Redgrave, 70, actress
Redgrave is not a woman for whom anything less than comfort in her clothing will do. She is not one to primp and truss, unless a role requires it. And she is blithely insouciant when it comes to items that make her life easy, from flip-flops to the scrunchies that usually form part of her outfit, even on red-carpet occasions. Simplicity is key, a point well taken by Vera Wang in the design she has been working on for the dress Redgrave will wear to the Tony Awards ceremony; she has been nominated for her performance in Joan Didion's one-woman play based on her memoir The Year of Magical Thinking.
Susan Train, 80 (in November), Vogue Paris Bureau Chief
She's tall, stately, slim, instantly recognizable. Always in immaculately cut pantsuits, she wears her clothes according to the norms of haute couture: the collar of her shirt turned up, her jacket pulled back a little to expose her neck. Her blonde hair has been cut short in the same style for as long as anyone can remember. She was sent to Paris in 1951 by Edna Woolman Chase (the editor in chief from 1914 until 1952), who told her, "I want you to be an island of Americanism in a sea of French." As Paris Editor, Bureau Chief, and now éminence blonde, she's Vogue's living history and an unwilling legend.
Connie Wald, 91, hostess
"I don't swoosh around much anymore," she says. "I need a lot of help." (In 1989, on one of her last trips abroad, she flew to Switzerland to surprise Audrey Hepburn on her sixtieth birthday.) She was able to swoosh sufficiently in 2000 in a black velvet T-shirt from the Gap with a black feather boa around her neck and an old Balenciaga black silk-taffeta floor-length skirt to attract the attention of Cathy Horyn, the fashion critic of The New York Times, who declared her one of the most elegant women present at Graydon Carter's Academy Awards party. In 2005, she was named to the Best-Dressed List.
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