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Oscar Style Winners 2009 – Best Dressed and Worst Dressed on the Red Carpet!

The 2009 Oscars are getting set to kick off tonight, but the red carpet specials are in full swing and there’s a lot to talk about when it comes to Oscar Fashion.

Unfortunately, much like the Golden Globe Awards and The Grammys, the fashion choices by some of the entertainment industry’s most notable fashionistas were less-than-impressive tonight.

Here are our lists of best dressed and worst dressed at the 2009 Oscars:

Best Dressed

It seems as though the younger generation is taking home the awards for best-dressed tonight. Miley Cyrus and Vanessa Hudgens both looked stylish (and age-appropriate) in floor-length black and white ball gowns. Natalie Portman also sparkled in a pale pinkish-purple gown with sexy makeup and a sophisticated updo.

Other mentions go to Jessica Biel, who dazzled in a champagne floor-length bow design gown and Heidi Klum who added a little bit of color to the red carpet in a fiery red off-the shoulder number and Katw Winslet who look fabulous in a dark silver floor-length gown and a fancy updo.

By far, the best dressed of the night goes to Angelina Jolie, who looked smashing in a classic black gown, gorgeous green emerald earrings, long whispy locks and natural makeup. Absolutely stunning. 

* Click Photos to Enlarge

Miley Cyrus 2009 Oscars Vanessa Hudgens 2009 Oscars Brad Pitt/ Angelina Jolie Heidi Klum 2009 Oscars Angelina Jolie Jessica Biel Kate Winslet 2009 Oscars Natalie Portman 2009 Oscars Jennifer Aniston

Worst Dressed

We don’t like handing out awards for worst dressed on the red carpet any more so than the next guy, but if they don’t want to be recognized as fashion failures then they shouldn’t show up to the most prestigious night in Hollywood looking like they got ready drunk.

Our awards for worst dressed at the 2009 Oscars go to Anne Hathaway, Beyonce and Amy Adams. Sorry ladies. Like we always say, better luck next year – if you’re invited.

Anne Hathaway Beyonce 2009 Oscars Amy Adams 2009 Oscars 

Check out our Angelina vs. Jen Oscar Night Faceoff!

Published Sunday, February 22, 2009 7:37 PM by Bella
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Comments

 

Hollywood Hookup : Angelina Jolie Oscar Photos 2009 - Best Dressed in Basic Black! said:

February 22, 2009 9:52 PM
 

Scrute said:

Angelina Jolie looked like a wicked witch and was her usual, unsurprising self. Black? Again? Can you imagine how dark and gloomy and expensive the inside of her closet must be? Why in the world should she be best dressed?

Miley Cyrus and Vanessa Hudgens were "age-appropriate"? Really? Cyrus looked like she was floating in her very own bubble of fluff. And Hudgens and Portman should have traded dresses!

By far, the most hilarious in your best dressed mention has to be Jessica Biel. Total disaster and my pick for worst dressed of the night. Boring color, bad cut, unflattering and uninspired overall.

Anne Hathaway was a win, classic, sophisticated and channeled old Hollywood GLAM!

February 23, 2009 1:57 AM
 

Hollywood Hookup : Angelina Jolie vs. Jennifer Aniston at the 2009 Oscars! (Photos) said:

February 23, 2009 8:53 AM
 

Sara said:

It cracks me up sometimes what people think is "hot or not."  I agree, the nots should be where they are, but some of the others don't make my list for attractive at all.  And BTW, Jennifer Aniston wins in my book! :)

February 23, 2009 9:50 AM
 

Cindy said:

Jen wins my vote! She looked fresh and that dress was just glam! I liked what she did with her hair, and her skin looked glowing! She looked beautiful!

Angelina Jolie looked worried, stressed and boring with the black dress...All the comments on the carpet were about how much light colors were in and she shows up in a black dress, yes it is classic but it just makes her look very "skeletor-like" did not like at all!

Mylie Cyrus-UGLY DRESS, that's all!

Beyonce- HORRIBLE DRESS! OH Dear God, that was ugly! Not that she's really known for leading the list of best dressed but this one is one of the worst I've seen on her!

I did like Jessica Biel's dress it was elegant with that very trendy touch of the "oragami" look that is so in right now! Her hair looked pretty

February 23, 2009 10:54 AM
 

Lena said:

You've gotta be kidding me.  Angelina Jolie as best dressed?  She was such a disappointment.  Her earrings were fab, but her dress was probably the most boring one there (as usual, lately).  Just because she could look gorgeous in a sack doesn't mean she's the best dressed.

I thought this was a no-brainer.  Kate Winslet owned that carpet.

(And yes, I agree with the comments before me.  Jen Aniston won this round against Jolie.  I wish the media's love affair with Jolie would stop because she gets duller and duller by the day.)

February 23, 2009 12:34 PM
 

Susan said:

I loved Angie's whole look. Those emerald earrings and ring just popped against the black!!! Anyone who thinks that because she wore black it was boring didn't see the detail up close and the sweetheart bustline looked amazing on her with her hair falling over her shoulders so elegantly. It is no surprise to me that she ended up on most best dressed lists and even at the top of the list on some sites. A classic beauty!

February 24, 2009 4:44 PM
 

Carrie said:

Worst dressed was Jessica Beil. By far. What the heck was that anyway? A towel? A bib? What????

February 24, 2009 4:45 PM
 

Lydia said:

No one has mentioned Tina Fey, her dress was glamorous and understatedly elegant.  Not to mention it looked fabulous on her.  Cheers to Tina!!! And yes, Beyonce's dress was hideous.

February 24, 2009 8:06 PM
 

Alecia said:

Angelina Jolie looked like she was sent from above.  I like Jennifer Aniston, but I wish she looked her best..the dress was alright but simplicity works best for her..a  natural look..the hair is where I digress..didn't care for the braid across the front of her head..strange..although it photographed much better than it appeared on stage.  She seemed nervous and awkward during the awards presentation..felt bad for her..hated that the production had to camera over to Pitt and Jolie..it was tacky.  I thought it cool of Hugh Jackman to joke over the whole matter, which makes it worse for them all.  I loved Jolie's look but she could wear a paper bag and look stunning...seemed as if she hadn't a care in the world.  I also thought Hathaway, Tomei, Cruz, Henson and Portman looked divine.  All goddess-like that evening.

February 25, 2009 10:40 PM

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