The Oscars: Worst Celebrity Dresses of All Time

Although they typically have a team of personal stylists, celebrities still manage to fall on the worst-dressed list from time to time. Whether they push the envelope just a little too much or go overboard with accessorizing, there’s no denying even our favorite stars have rocked some pretty horrendous outfits.

When it comes to what is arguably the biggest celebrity night of the year — the Oscars — there is more pressure than ever to look good. Even with designer gowns, stylists, and makeup artists, we continue to see celebrity dresses crash and burn on the red carpet. Want to see some of the worst? Look no further. The following celebrity missteps are listed by year in ascending order.

1. Lizzie Gardiner, 1995

Australians Lizzy Gardiner and Tim Chappel, the former is wearing a dress made out of AMEX cards

Australians Lizzy Gardiner and Tim Chappel | Dan Groshong/AFP/Getty Images

This dress might be one of the worst. While it’s obvious that Lizzie Gardiner is trying to make a statement, it’s unclear what that statement might be. Gardiner wore a dress made out of 254 expired American Express Gold Cards. Even though she’s a costume designer, it’s clear she should have left the designing of her Oscar dress to someone who has a little more experience in the glamour department.

2. Susan Sarandon, 1996

Actress Susan Sarandon and director Tim Robbins at the 68th Annual Academy Awards, the former is wearing a bronze satin dress

Actress Susan Sarandon and director Tim Robbins at the 68th Annual Academy Awards | Vince Bucci/AFP/Getty Images

What makes this dress choice even worse is Susan Sarandon accepted an Oscar for Dead Man Walking while wearing this giant bronze poof. Not only were the never-ending folds of fabric too much, but the color somehow managed to match her spiky hairdo perfectly. The sunglasses took the gown over the top, landing it right where it belongs: on our worst-dressed list. 

3. Celine Dion, 1999

Academy Award winning singer Celine Dion who is wearing a backward white suit

Academy Award-winning singer Celine Dion | Vince Bucci/AFP/Getty Images

There’s something sexy about a woman rocking a suit, but Celine Dion took it too far with this all-white ensemble. The pants looked too wide and too long on the petite singer, and for some reason, she chose to wear the tuxedo from John Galliano for Christian Dior backward. Dion took it one step further by wearing a white satin hat and jeweled sunglasses. Bad choice, Celine.

4. Bjork, 2001

Actress and singer Bjork who is wearing a dress that looks like a swan

Actress and singer Bjork | Lucy Nicholson/AFP/Getty Images

Being emulated by Ellen DeGeneres at the Emmys and Kevin James at the People’s Choice Awards, Bjork’s swan dress has seen its fair share of parodies. Although most of us can’t believe she actually wore a swan dress on the red carpet, others have recognized it as an iconic gown. In fact, it was reimagined by Valentino at 2014’s Paris Fashion Week. 

5. Faith Hill, 2002

Singer Faith Hill and actress Cameron Diaz, the former is wearing a rainbow dress with a feather pattern

Singer Faith Hill and actress Cameron Diaz | Lucy Nicholson/AFP/Getty Images

When country singer Faith Hill was scheduled to sing “Somewhere Over the Rainbow” at the 2002 Academy Awards, she couldn’t resist donning a rainbow gown for the occasion. Unfortunately, for a classy event like the Oscars, the pastel Versace gown was just a bit too much. The dress was a range of rainbow hues in a pattern that looked like layered feathers — not the most flattering choice.

6. Diane Keaton, 2004

Actress Diane Keaton in a full suit with a polka dot die, bowler hat, and grey gloves

Actress Diane Keaton | Vince Bucci/Getty Images

This getup from 2004 isn’t even a dress, but it’s still one of the worst Oscar outfits we’ve seen to date. The Ralph Lauren creation pushes the feminine take on the suit too far. The details and accessories only make matters worse, with the outfit’s polka-dot tie (and matching handkerchief) and long tails. The topping on the cake are those mock-wingtip oxford shoes.

7. Uma Thurman, 2004

Actor Jude Law and actress Uma Thurman who is wearing a makeshift white dress with a blue sash

Actor Jude Law and actress Uma Thurman | Kevin Winter/Getty Images

2004 must have been rough at the Oscars, as this is the second star we’ve had to call out from that year. What is there to say about this dress? It literally looks like it was thrown together at the last minute — by a 5-year-old. The bunches of layered, bulky fabric do nothing for the star.

8. Marion Cotillard, 2009

Actress Marion Cotillard in a long black dress

Actress Marion Cotillard | Frazer Harrison/Getty Images

At first glance, this dress doesn’t seem too bad. But then you notice the shiny faux leather belt and the silver spring hidden beneath the tulle, and it all goes downhill from there. Luckily, Marion Cotillard pulls it off better than most.

9. Sophia Loren, 2009

Actress Sophie Loren in a mustard yellow dress

Actress Sophie Loren | Kevork Djansezian/Getty Images

This dress might be one of the worst. The dijon mustard color is overdone, and the Armani dress has one too many swirls and textures. In this case, the Italian actress would have been better off choosing a simpler, more understated gown.

10. Charlize Theron, 2010

Actress Charlize Theron in a purple gown with roses on the chest

Actress Charlize Theron | Jason Merritt/Getty Images

Another Oscar misstep came from actress Charlize Theron. John Galliano made the dress for Dior. The roses — or purple cinnamon buns, as they’ve been called — only made Theron’s dress look awkward in all the wrong ways.

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