Best and Worst Oscar Dresses

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Truly gorgeous (and hideous!) red carpet looks

1/20

Julia Roberts
Best, 2001

Valentino can do no wrong! Our fave pretty woman rocked this gorg look in 2001, making her one of our choices for best dressed!

2/20

Penelope Cruz
Best, 2007

We couldn’t think of a better combo than Penelope Cruz and Versace! She stole the show in 2007 with this gorgeous and elaborate gown.

3/20

Celine Dion
Worst, 1999

A backward white suit, dark shades, and a hat? Sorry Celine, but you look like an insane Good Humor Man.

4/20

Shirley MacLaine
Best, 1975

Classic and glamorous, this star’s sparkly gown was an instant hit, and landed her on the Best Gowns of All Time list.

5/20

Kate Hudson
Best, 2003

Another Versace hit! Kate Hudson is glowing in this gorgeous gown with her vintage jewels.

6/20

Whoopi Goldberg
Worst, 1993

Whoop…sie. This dress reminds us of a Disney villain. Maleficent from Sleeping Beauty, anyone?

7/20

Michelle Williams
Best, 2006

Stunning in Vera Wang! Loving Michelle’s bold choice of color, tied together with the red lips.

8/20

Lauren Bacall
Best, 1952

Move over Cate Blanchett, because there’s a new (er, old) pregnant stunner on the carpet! Humphrey Bogart’s special lady and baby looked fierce in Christian Dior at the 1952 Oscars.

9/20

Cher
Worst, 1988

If we could turn back time, we’d have a chat with her stylist. Or hire her one.

10/20

Sharon Stone
Best, 1998

The daring Ms. Stone used her basic instincts when she paired her husband’s Gap button-down with a lilac satin Vera Wang skirt, and we’re loving it!

11/20

Grace Kelly
Best, 1956

Look up the word “glamour” in the dictionary and you will find a pic of Grace Kelly at the 1956 Oscars. The real-life princess looked regal in a Helen Rose creation.

12/20

Björk
Worst, 2001

Sorry Björk, you’re a few years early for the role of the Swan Princess! We love original pieces, but some should be left in the closet (or the oven).

13/20

Natalie Portman
Best, 2005

A Greek goddess in gray, Natalie Portman topped off this Lanvin creation with a diadem and minimal accessories. Gorg!

14/20

Audrey Hepburn
Best, 1954

Romeo and Juliet…Kate and Will…Starsky and Hutch…Some people are just meant to be together. Hubert de Givenchy and Audrey Hepburn were no exception, and our fave waif dazzled her way into America’s heart wearing Givenchy’s glamorous design in 1954. Talk about a perfect fit!

15/20

Kim Basinger
Worst, 1990

Runaway bride or the 1990 Oscars? To be determined. Sorry Kim, not your best!

16/20

Mila Kunis
Best, 2011

We wish we were just friends with Mila Kunis so we could borrow her uh-mazing lavender Elie Saab haute couture gown from the 2011 Oscars. Wow!

17/20

Jennifer Aniston
Best, 2009

It was a pleasant surprise when the queen of the LBD changed it up and made an appearance in this gorg Valentino number. One thing that remains unchanged: her gorg glowing tan!

18/20

Hilary Swank
Worst, 2003

The sheer and the shades of pink are just all wrong for an Oscar dress, or maybe for any dress!

19/20

Nicole Kidman
Best, 2007

The Balenciaga-clad beauty’s red scarf followed her all night at the 2007 Oscars…as did the eyes of every person on the carpet.

20/20

Giuliana Rancic
Best, 2011

Let’s all say it together: fierce! G dazzled in an aqua printed Christian Siriano creation at the 2011 Oscars. Amazeballs! And no, we’re not at all prejudiced. Not one bit!!

Posted on February 22, 2012

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