24 Stars Who Got Dressed In The Dark For The Oscars — Worst Dressed Of All Time

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In honor of Oscars weekend quickly approaching, we decided to take a trip down memory lane. The Oscars are the biggest night of the year in Hollywood & while we always see some of the most gorgeous dresses, we also see some of the worst. We rounded up the worst dressed celebs of all time at the Oscars & we can’t decide which was the worst. What do you think? VOTE.

The Academy Awards are almost here and it is by far our favorite night of the year because we get to see all of our favorite celebrities from Hollywood arrive on the red carpet in gorgeous dresses. Most of the time we love the celeb looks but we have to admit that over the years we have seen some of the worst dressed celebrities of all time. So, we rounded up our top worst dressed looks and we can’t decide who looked the most like they got ready in a hurry. What do you think? VOTE.

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Let’s start with Madonna, 58, because she is known for her eccentric outfits, but her 1999 Oscars look was pretty awful. She opted to wear a long black off the shoulder tunic with matching baggy pants and the entire outfit was covered in metallic gold floral print — it looked like she was in her pajamas.

Next up, Gwyneth Paltrow, 44, opted for quite the revealing dress in 2002. Gwyneth went completely braless underneath her Alexander McQueen gown which featured a sheer gray bodice and a long ruffled skirt. She went full blown goth in this look and added a ton of dark makeup and a silver pendant necklace.

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Anne Hathaway, 34, went with a very loud dress back in 2004 when she donned this skin-tight satin orange gown with colorful floral print all over it. The dress had a plunging neckline showing off massive cleavage and an open back — definitely not our favorite.

Last but never least, Hilary Swank, 42, looked like she was going to the prom and not the Oscars back in 2003. Hilary showed up in a pink ombre tulle gown with a sheer hot pink overlay on top of a white mini dress. Her dress looked like what you used to wear when you played dress-up as a kid.

It is so hard to choose who was the worst dressed of all time at the Oscars! What do you guys think? VOTE.