10 Worst Oscar Dresses of All Time ...

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Worst Oscar dresses are quite memorable, even though the stars that wore them would no doubt rather forget them. As you’ll see below, there’s no set formula for what makes a worst Oscar dress. All we know is that when worst Oscar dresses happen, our eyes cry. With the Oscar season wrapped up for another year, let’s look back in red carpet history to relive some of the worst dresses at the Oscars.

1. Uma Thurman – 2004

Uma Thurman – 2004

I’m not quite sure what Uma or her stylist was thinking when they chose this ensemble (did she even have a stylist?

If so I hope she fired them promptly after this).2

The poufy sleeves, the blue sash… it all seems a bit Sound of Music meets the Oscars, and it doesn’t work well at all!2

2. Whoopi Goldberg – 1993

Whoopi Goldberg – 1993

Two colours you should never wear to the Oscars, if you were ever invited?

Purple and lime green, as evidenced by this creation that Whoopi wore in 1993.2

She also took matching accessories to the next level with shoes that matched her printed pant suit.

3. Cher – 1988

Cher – 1988

Cher’s history is littered with questionable fashion choices, and who could forget this revealing Bob Mackie creation she wore to the Oscars in 1988.

Definitely a candidate for one of the worst Oscar dresses in history.

At least she brought the scarf as a cover up?

4. Kim Basinger – 1990

Kim Basinger – 1990

I really don’t know where to start with this dress, but it definitely takes the cake for one of the worst Oscar dresses.

It’s a bit schizophrenic, with the menswear inspired half jacket, poufy ball gown skirt, and single evening glove.

Who designed it, you ask?

Kim Basinger.

She should stick to acting.

5. Demi Moore – 1989

Demi Moore – 1989

So I knew bicycle shorts were big in the 80s, but under no circumstances did I think anyone would ever wear them on the red carpet.

But Demi did, in a creation she designed herself.

Are you starting to see a pattern here?

Faith Hill – 2002
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