Chelsea Handler Dressed Like a Man for 'Glamour' Awards

chelsea handler and jennifer anistonOn Monday, Glamour magazine gave 11 women the title of "Woman of the Year" at its annual fete celebrating the all-mighty female. Winners this year included Jennifer Lopez, Chelsea Handler, Lea Michele, and almost every lady in the Bush family. It looked like a super fun party and it's a shame my nomination announcement got lost in the mail because I would've loved to have been there in the dressing room with Chelsea and her best friend and presenter, Jennifer Aniston. I could've turned on the lights in there for them because clearly they forgot. It's obvious they got dressed in the dark.

Jen wore a mullet dress and Chelsea wore a jumpsuit. Let's discuss.


We all know Chels is a big vodka fan -- maybe those two crazy kids were hitting the sauce while getting ready. Did Jen dare Chelsea to wear a navy one-piece? Did Chelsea dare Jen to cut off the front of her dress? I know their outfits cost a small fortune, and if I had to guess, Jen's dress is vintage Versace or YSL, but they weren't looking their best. And for such a big night, you'd think they'd try a little harder.

And their dueling cleavage was a bit distracting. I don't know whose boobs to stare at first! There's one thing I did really love about their looks, though: Jen's amazing plastic surgery. She's six years older than Chelsea but she looks eight years younger. And she looks so comfortable in her own skin ... Chelsea looks less so.

I love that these two are friends, Jen once said that she only went on Chelsea's show so that the comedian wouldn't talk smack about her, but it's obvious that they're now best buddies. Jen introduced Chelsea by saying she was "madly in love" with her (take that Theroux) and we've seen the pair out and about in Mexico and at dinners in L.A.

But best friends don't let best friends wear a heinous, ill-fitting navy blue jumpsuit on the red carpet. We'll let Jen get away with her mullet dress, but Chelsea's getting a conviction. The fashion police are not pleased. Next time, lay off the dirty martinis while getting prepped and turn on the lights -- we don't want another fashion faux-pas.

What do you think of Jennifer's dress and Chelsea's suit?


Photo via Dimitrios Kambouris/Getty

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