Natalie Portman and Debra Messing attend the 2008 Glamour Women of the Year Awards at Carnegie Hall in New York City.
Jolibe Fall 2008
She looks great. It's a beautiful dress and she wears it well. Hate the shoes but she's into that whole vegan shoe thing and that doesn't always translate into pretty. IN.
Ralph Lauren Fall 2008
It's a pretty dress on the model but it's not working for Debra. We're not quite sure why. Maybe because she's about 20 years older than the model and a couple of sizes larger, but it's just not doing her figure any favors. She looks schlumpy. It also doesn't help that her styling is so severe and she could have used a couple of big pieces of jewelry to set off the dress. The model's earrings help make the look and Debra's are practically invisible. OUT.
[Photos: WireImage/Getty Images/Elle.com/Style.com]