She attended a Christian Dior runway show at the age of seventeen and was wearing insidery labels like Viktor & Rolf, but Leelee Sobieski insists that fashion was a foreign language to her until recently. “When I was younger, I made some disastrous decisions,” says the 29-year-old actress. “I probably should have had a stylist. I just wasn’t paying attention.”
And yet now, still dressing without professional counsel, Sobieski has emerged as one of the most stylish celebrities on the red carpet. She credits the influence of her husband, menswear designer Adam Kimmel, who custom makes women’s pieces for his wife, but it has just as much to do with her sophisticated, thoughtful choices. Consider her turns in a quiet but quirky label like Boy. by Band of Outsiders for a mainstream movie premiere, or her loyal allegiance to Raf Simons, who shares her appreciation of understated elegance. “I like clothing on a woman when it enhances the woman. I like jewelry on a woman when it enhances the woman,” says Sobieski, who with her patrician bone structure, elegant carriage, and signature red lip, can elevate jeans and an American Apparel T-shirt to Best Dressed status. Here, a look at ten of her most stylish moments.