Playing Dress Up with Oscar's Glamour Girls

Tilda Swinton

Swinton is an extraordinary actress with a sensational career. At 47, she scored a best supporting actress nom for her role in "Michael Clayton." Though Swinton is fearless when it comes to fashion and is respected for often making over-the-top choices with daring European designers like Viktor & Rolf, she is no stranger to the worst dressed lists of many fashion savants. But it is this free spirit that enables her to march to the beat of her own stylish drummer. So, as my old Studio 54 buddy and "America's Next Top Model" judge Miss Jay and I reveled in Carolina Herrera's hunting-inspired fall 2008 collection, I knew the catch of the day for Swinton was this subtly elegant gown in the richest of luminescent coppers.

Tilda Swinton/Carolina Herrera

The gown would compliment her amber hair and fair and flawless complexion. And the decadent yet refined touch of plumage that doubles as both a belt and an origami-esque bow at the back of the dress, trailing behind like a mysterious aura, would certainly appeal to this dedicated fashionista. I often believe that only the right designer can understand a certain type of client and Herrera is truly one of the most distinguished, chic and talented women I know in the business. I think there would be an uncanny creative fusion if this dynamic duo would collaborate and listen to me about this dress on Oscar night. It's the perfect connection of high drama, European elegance, and fashion fantasy. This is the look Hollywood legends are made of.

Ruby Dee

Ruby Dee is 83 years old and as elegant as ever. Her career has spanned decades, though this is her first Oscar nomination — and it's been a long time coming. I have long admired her work and commitment to her husband, the late Ossie Davis, and was excited to meet her at Star Jones and Al Reynolds' Hamptons house this summer. She was so charming and entertaining. You could spend an entire day laughing and talking to this genuinely loving creature and her touching performance as a supporting actress in Ridley Scott's "American Gangster" is perfection.

While dress hunting for Dee, I thought about all the tricks of the trade stylists keep filed in our minds when dressing a leading lady of a certain age. The look must be dignified but not stuffy and old fashioned. So I instantly thought of a fashion icon — Valentino — to dress this film icon. Valentino just presented his final couture show in January in Paris so what better place to choose from?

Ruby Dee/Valentino

I naturally gravitated toward the simple elegance of this Jackie Kennedy/Audrey Hepburn-esque one-shouldered sheath. The white would be classic elegance at its best. I even love the opera length gloves. Though, of course, we would have to alter the proportions of this look to accentuate Dee's petite stature but not compromise her enormous sense of style. And for Dee, I'd go for the glam with diamonds — a gorgeous bracelet over the glove and a dangling earring that gives the luster and sparkle that only a girl's best friend can deliver.

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