Back in January 2008, Debra Messing glided down the red carpet at the 2008 SAG Awards wearing an Oscar de la Renta Spring 2008 gold embellished halter gown.
For me it still ranks as one of her best ever red carpet moments.
Natalie Cole wore the same dress to the 2011 Angel Ball in New York City last month.
The singer looked sensational in this gown, but she overloaded it with too many jewels when the dress didn’t need any extra bling so Debra wins for me.
If you can’t decide, click on the image above to see more pictures of these ladies in their Oscar de la Renta gown.

Credit: Style.com & Getty
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Posted by Catherine Kallon on November 16th, 2011 In: Debra Messing, Natalie Cole, Oscar de la Renta, Who Wore It Better?










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Such a beautiful gown! You’re right. Definitely Debra!
Debra looks sensational in this, she wins hands down.
Debra’s hair just isn’t working for me, but I can live with it compared to over accessorizing. So she wins for me as well.
Natalie’s skin-colour takes this dress to a whole new level. Absolutely fantastic.
I was madly in love with Natalie in this dress but seeing Debra I have to say I’m torn. I’m actually loving Debras dishevelled bed hair as a contrast to this dramatic Cleoptra style gown. Very Modern Queen / Goddess. I might have to give my vote to Debra for keeping the whole look simply beautiful.
I didn’t vote, because Debra looks better but I can’t overlook the messy hair. Natalie wore too much jewelry.
I can overlook the overaccessorizing when the fit is so much better on Natalie, when the gown looks so much more spectacular on her esp. against her skin tone. Natalie wins for me.
i agree
amazing gown and natalies clutch is amazing to.