40+ of the Best and Worst Oscar Dresses of All Time

It’s red carpet season again, and we’re here for ALL the glitz and glam Hollywood brings! The Academy Awards, aka the Oscars, are the pinnacle of award season, so you’re guaranteed to see nominees and guests sporting all the bells and whistles that top designers can muster. But are all these dresses what they’re cracked up to be? Some are memorable in a good way, whereas others are not. Let’s see who made their mark on our scale of best and worst.

Angelina Jolie - 2004

The brunette beauty wore a classic-looking satin halter dress designed by Marc Bouwer. While not over-the-top, its sultry subduedness made it stand out among the rest on that night. The creamy white of the satin shone against Angelina's tan skin, and the whole look gave us Marilyn Monroe vibes.

Angelina Jolie - 2004

Some have declared this dress an Oscar winner, and it absolutely qualifies to be on this list! Angie definitely knows how to put her best look forward.

Audrey Hepburn - 1953

One of the world's most adored actresses, Audrey Hepburn, never failed to make her mark wherever she went. Back in the early days of the Oscars, the ceremony wasn't the pomp and ceremony it is today, and cocktail dresses were the norm. Audrey, winning Best Actress for Roman Holiday, looks positively stunning in this white Givenchy dress.

Audrey Hepburn - 1953

It's no wonder she wore a Givenchy design, as she was great friends with Hubert de Givenchy. The unique boat neckline showed off Audrey's slim neck and perfect posture, and that style wasn't common for such an occasion. It's no wonder it's been a celebrated Oscar design since then.

Bjork - 2001

Well, what can we say here? It makes a statement, that's for sure! The Icelandic singer was covered in feathery tulle and a swan's neck draped around her neck, ending with its head strategically covering her chest. Not only did she wear this dress, but she, um, laid eggs walking down the red carpet!

Bjork - 2001

Although this dress was (and still is) certainly capturing negative attention at the time, we have to conclude that it's become iconic all these decades later.

Catherine Zeta-Jones - 2003

No stranger to red carpets, this Welsh actress walked away with the Best Supporting Actress for her role in Chicago. At the time, Catherine was heavily pregnant with her daughter, Carys, but Versace came through for her and created a stunning gown in an unusual yet complimentary color.

Catherine Zeta-Jones - 2003

We can't imagine being all dressed up and having to sit through an entire Oscar ceremony as it is, but being nine months pregnant as well?! At least the dress looked comfortable!