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Jessica Simpson, International Youth Ambassador for Operation Smile, was on hand last night at Cipriani Wall Street in NYC for the 2010 Operation Smile Annual Gala. The star-studded event was well attended and we’ve got the red carpet photos.

We find it somewhat ironic that Simpson doesn’t brush her teeth on a regular basis because she can’t stand “that squeaky clean feel”. In an interview earlier this week she said, “I do brush every now and again. I just use Listerine — and sometimes I’ll use my sweater.”

The non-profit organization raises money to provide surgery for children worldwide who are born with cleft lip and palate. The group has provided reconstructive surgery to over 140,000 children and young adults in more than 50 countries since it was founded in 1982.

Simpson has been rumored to be romancing with actor Jeremy Renner. Initial sightings occurred last weekend when the pair was in Washington D.C. for the Correspondents’ Dinner. The couple were spotted entering the same hotel within 30 seconds of each other at the end of the evening. We’ve just have to see where this one goes.

Also attending the Operation Smile Gala last night were Donald Trump Jr. and his wife Vanessa, actress Stephanie March, model Lydia Hearst, Tinsley Mortimer, Dabney Mercer, model Jaslene Gonzalez, hair guru Ken Paves, singer Sasha, Olivia Palermo, model Sessilee Lopez, Nick Cannon, and CNN anchor Nicole Lapin.

Check out the gallery below:

Photos: L. Gallo: WENN