The Best and Worst Oscar Looks of All Time

While the Academy Awards take place every year to recognize excellence in film, the gowns are often more memorable than the movies themselves. In order to prepare yourself for this year’s Oscars, here’s a look back on some of the best and worst Oscar gowns of all time.

Worst

Some looks are so bad that we remember them for years.

Geena Davis

This 1992 dress was a culmination of all things 90s, but in the worst way possible. The sheer tights, weird length, and unflattering ruffles have gotten even worse with age.

Kim Basinger

Basinger designed her own gown for the 1990 Oscars, but this is proof that she probably should have left her gown choice to her stylist. The gown looks like a strange mishmash between Cinderella and Judy Jetson.

Alicia Vikander

This 2016 look was reminiscent of Belle from Beauty and the Beast in the worst way possible. This look is better suited for a cartoon and not a red carpet.

Demi Moore

Bike shorts are work best in the gym and not on the red carpet. Moore seemed to forget the dress code for the red carpet when she wore this look to the 1989 Oscars.

Whoopi Goldberg

This 1993 look suffered from too many colors and an unflattering silhouette. The dress was made even worse by the addition of matching shoes.

Helena Bonham Carter

Bjork

Sometimes taking a risk pays off. Other times, not so much. This is a case where Bjork’s fashion risk at the 2001 Oscars looks like she had just gone hunting and was wearing her kill around her neck.

Brandi Glanville

Glanville broke the #1 rule for Oscar gowns in this 2013 dress: make sure your dress fits you! Glanville’s dress seemed to be falling off, cheapening the look of this self-designed dress.

Jennifer Hudson

Hudson wore this dress to the 2007 Oscars. There were two major problems with it: the brown and silver didn’t match, and the jacket was unflattering.

Angelina Jolie

At the 2000 Oscar’s, Jolie wore this dress that was reminiscent of Morticia Addams. Combined with her odd antics on the red carpet, Jolie looked more prepared for a funeral than a red carpet.

Best

It’s always good to save the best for last! So enjoy these best Oscar looks of all time.

Audrey Hepburn

This 1954 gown was designed by Hepburn’s longterm collaborator, Hubert de Givenchy. This classic look has stood the test of time, remaining one of the best Oscar looks ever.

Anne Hathaway

This 2008 Oscar gown combined elegance with interest. The red color flattered Hathaway’s porcelain skin, and the draping flattered her figure.

Cate Blanchett

The 2014 Oscars was the night in which Blanchett became an Oscar winner, and Blanchett dressed to be a winner. This sparkly gown helped Blanchett stand out on the red carpet, and the classic shape flattered Blanchett’s figure.

Michelle Williams

Canary yellow is an unusual color for red carpet gowns, and William’s risk paid off in this case. The Vera Wang gown that Williams wore for the 2006 Oscars helped her look as good as Oscar gold, even if she didn’t end up winning that night.

Grace Kelly

This icy blue gown that Kelly selected for the 1955 Oscars is still talked about today, over sixty years later. Kelly exudes the lusted-after Old Hollywood glamor.

Lupita Nyong’o

Unlike some other people on this list, Lupita Nyong’o went for Cinderella moment in this gown at the 2014 Oscars and made it work. The sky blue color flattered Nyong’o’s rich skin tone.

Gwyneth Paltrow

While many of Paltrow’s previous Oscar gowns are memorable, this one takes the cake. The simple column design was made memorable through the addition of a cape, which read chic not superhero.

Octavia Spencer

This 2012 gown was memorable because it was so different from other gowns previously seen on the red carpet. The short-sleeved dress flattered Spencer’s figure and made Spencer’s Oscar win that much more memorable.

Adele

Usually wearing black on the red carpet is boring and predictable, but this 2013 gown broke all those rules. Adele’s dress was made interesting through a unique cut and beautiful beading.