Crazy Trains and a Donna Karan–Christopher Bailey Love Affair at the CFDA Awards

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Whitney Port, Iman, Sarah Jessica Parker. Photo: Dimitrios Kambouris/Getty Images, Andrew H. Walker/Getty Images

We get the appeal of wearing a dress with a giant train to a fashion event, but the cocktails-only setup for last night’s Council of Fashion Designers of America Awards pre-party and after-party ensured that those who did were greeted by many an unsuspecting high heel. Even we almost tripped over the train on Whitney Port’s silver David Meister dress. (She wasn’t wearing her own design because she doesn’t make formalwear — yet.) “It’s okay. Whatever,” she said, rather blithely. “I don’t really care. Like, if people want to step on it, they can step on it. It’s not going to fall off. I’m fine.”

Sarah Jessica Parker, who wore a stunning McQueen gown personally picked for her by Sarah Burton, took an equally relaxed view. “With all that’s going on in the world, if I can’t manage my train, I shouldn’t even be called human,” she said, “This is one of those burdens I can’t complain about. Just lean over and pick up the train. Pick it up! You can’t be modest; there’s no delicate way to do it.”

And Iman, there to receive the CFDA’s Fashion Icon award, decided it simply wasn’t her job to be in charge of the trail of black feathers at the bottom of her Giambattista Valli gown. “I am the icon,” she said. “They can walk around.”

Iman’s efforts to embody her icon status were among the most delightful moments of the evening. In her speech, she thanked her mom and dad for giving her “a neck longer than any other girl on any go-see anywhere in the world,” and thanked everyone present “for the right to finally say to my husband, ‘You’re not the only icon in the house.’” Afterward, she told us that David Bowie has started calling her “icon” and exits every room she’s in backwards, bowing and repeating, “Icon, Icon, Icon.”

Other great backstage moments included Geoffrey Beene Lifetime Achievement Award recipient Michael Kors and Womenswear Designer of the Year Marc Jacobs embracing and saying to each other, “We have been around! Honey, have we been around!” Moments later, Kors explained: "Listen, I remember shows we did where he had a boom box and a tape and I was, like, painting earrings. We’ve known each other a long, long time. I was at Marc’s graduation show for Parsons!”

Also extremely hug-prone were Donna Karan and International Award Winner Christopher Bailey, who Karan had discovered fifteen years earlier by chance while visiting his art school in England. Bailey explained that they were practically in love the moment they met. “I remember it so vividly,” he said. “She wanted to try on everything I’d made. We stayed at school until the door had been locked and the college had to come up and say, ‘Guys, you’re going to have to leave now.’ And she took a picture of me and said, ‘Call me. I’d love for you to work for me.’ I’d never been to New York; I’d never even been to America. So Donna is the one who bought me my first plane ticket to America.” At that moment, Karan came up and wrapped her arms around Bailey’s shoulders. “I think he should come back to work for me and we can discuss him. I’m going to ask him. Watch out! Have you had enough of London, honey? New York is waiting for you. I’m waiting for you.”

As soon as the awards were parceled out, Iman and David Bowie headed off to a mysterious dinner location to celebrate their eighteenth anniversary, just the two of them. But for everyone else, it was time to drink. Michael Kors declared he wanted anything but red wine: “I wear black; I drink white.” Normally quiet Jason Wu was also ready to throw down. “Shots! After-party!” he said, hoisting his Swarovski Award for Womenswear. “I always like tequila. That’s classic and it’s low-calorie, because you’re not doing any of the sugary mixers. Straight up — that’s the trick. With a little lime.”

There was further revelry to be had at the Top of the Standard, though we were too exhausted to check it out. As we switched into flats and headed toward the subway, we spotted both wives of rag & bone designers David Neville and Marcus Wainwright (winners of the Menswear Designer of the Year award) walking barefoot down the middle of 65th Street, their husbands holding the silver statue in one hand and a pair of high heels in the other — a beautiful, messy image of the joys and pitfalls of fashion that'll hold us over till next year.

See the full list of CFDA winners here, or scope our behind-the-scenes slideshow.