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Maggie Gyllenhaal Chats With Anna Wintour, Wears Tuxedo Jacket (PHOTOS)

First Posted: 06/04/10 11:48 AM ET   Updated: 05/25/11 05:40 PM ET

Maggie Gyllenhaal hit the red carpet for the Fresh Air Fund's Salute to American Heroes on Thursday night in New York. She donned a long black maxi dress with caramel-colored pumps, and wore her hair curly, possibility to combat the city's insane humidity. Once inside Pier 60, she slipped on a tuxedo jacket and chatted with Anna Wintour. What do you think they were discussing? And what do you think of Maggie G.'s get-up?

2010-06-04-maggiegyllenhaalannawintour.jpg

2010-06-04-maggiegyllenhaal.jpg

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02:38 PM on 06/14/2010
Anna could have a cheeseburger .. poor thing is so skinny. -- but I actually like her dress.

Maggie's dress is not pretty at all, and certainly not with those ugly shoes.
08:03 AM on 06/06/2010
Those shoes!
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LMPE
I connect the most dissimilar things
01:22 AM on 06/06/2010
These two would look neat in togas.
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lainey
Always remember Troy Davis.
12:43 AM on 06/06/2010
Beautiful women in beautiful dresses.
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Lozange
Aiming around wondrously
09:21 PM on 06/05/2010
I guess it's de rigueur now for beautiful people to actually be homey.
08:17 PM on 06/05/2010
Run, Maggie, run! Wintour bites the heads off her mates! And she's bisexual!
07:38 PM on 06/05/2010
Does anyone know the maker of Anna's dress? I adore the fabric - so pretty!
05:13 PM on 06/05/2010
the best i've seen maggie look! anna never looks good
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LaurieAnn
Wake Up! Grow Up! Lighten Up!
02:07 PM on 06/05/2010
Maggie looks outstanding once again. I love her hair as well.
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lainey
Always remember Troy Davis.
12:44 AM on 06/06/2010
I agree on both accounts.
05:48 AM on 06/05/2010
maggie looks great. i also love the brown shoes - unexpected. maggie has style, she doesn't wear louboutins like your average carrie bradshaw.
08:35 PM on 06/04/2010
Nobody shoots the breeze with Wintour. Ain't ever going to happen.
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love8rockets
02:45 PM on 06/04/2010
Maggie looks great--um the shoes were off putting. Anna wintor is a Fur Ho!
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mssreader
eat, read, sleep, read and be happy
02:42 PM on 06/04/2010
Maggie awfully cute but did she put on the wrong shoes. As for Anna's lack of a smile, does this have something to do with PS or botox and she has a rule against smiling! She has rather strange lips. That's ok because Maggie's smile lights up the whole room.
05:49 AM on 06/05/2010
suprised at your comment - anna is smiling on the right there. :)
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Daws
Wants to go to there.
01:05 PM on 06/04/2010
She looks very elegant. Talented actress. I love want Anna is wearing too.
12:28 PM on 06/04/2010
Love the tuxedo jacket, not sure about the shoes, though.
02:37 PM on 06/04/2010
Yes, surprised she didn't wear sandals of some sort. Unless she was due for a pedi . . .