Celebs Smile At Operation Smile's New York Gala

Even those stars with really white, slippery teeth were on hand to celebrate the 2010 Operation Smile annual gala at Cipriani Wall Street. Think J.Sim, the Tinz, Nick Cannon, award-winning moddle Lydia Hearst, Mr. Jay...

Celebs Smile At Operation Smile's New York Gala

Jessica Simpson: not afraid of a pattern - or 10. I will say this for it: they don't wear her. Maybe it's the blinding glow of her teeth.


Celebs Smile At Operation Smile's New York Gala

I'm rapidly coming to the conclusion that I don't like silk jersey. When it looks kinda schleppy even on Stephanie March aka ADA Alex Cabot aka Mrs. Flay, well, you know it's the fabric.


Celebs Smile At Operation Smile's New York Gala

One of my friends was like, "what's your deal with the bandage dress?" THIS! This is my "deal" with it! (No disrespect to Nicole Lapin, who is, I'm sure, a lovely person.)


Celebs Smile At Operation Smile's New York Gala

Also, what's with me and ombre? I don't know - bad associations. Actually I do know, and it has a lot to do with this one Caldor dress in which I was humiliated at a birthday party circa '88. Really, nothing to do with Vanessa Trump.


Celebs Smile At Operation Smile's New York Gala

Lovin' Olivia Palermo's vintagey tiers. (Although, are those fur pom-poms...?) Am confused by the purse and the business pumps. And I'm not ashamed to admit it.


Celebs Smile At Operation Smile's New York Gala

Speaking of retro: Sasha's all set to do Pink Lady-at-prom!


Celebs Smile At Operation Smile's New York Gala

And yes, award-winning model Lydia Hearst, we get it: "flapper."


Celebs Smile At Operation Smile's New York Gala

This is causing me cognitive dissonance, because Tinsley Mortimer is, like, professionally rich. And yet this dress looks like she got the fabric from a thrift shop remnant bin and threw on a Forever21 belt. And I'm not saying we haven't all done that, but, you know.


Celebs Smile At Operation Smile's New York Gala

Let's talk Nick Cannon. Specifically, the fact that the man rocks black tie.


Celebs Smile At Operation Smile's New York Gala

Let's talk Jay Manuel and the fact that he's apparently allergic to the unembellished.


Celebs Smile At Operation Smile's New York Gala

My personal fave of the evening, Jaslene Gonzalez' steel magnolia. (Too bad it seems to be falling off.)


[Images via Getty.]