POPSUGAR Celebrity

Oscars Beauty: Iconic Missteps

Feb 17 2009 - 12:02pm

Here's the post you've been waiting for: Iconic Missteps of Oscars past. Knowing how much you enjoyed seeing questionable hair and makeup of the Grammys [1], I've assembled a montage of some not-so-hot looks from the Academy Awards, too. Check out a selection of awkward choices throughout the years, and try not to giggle too much.

And don't forget — I'll be posting live Love It or Hate It polls on all the Oscar looks on Sunday, so come back and we'll have a Bella beauty party!

Source [2]

Renee Zellweger, 1999

Hard to believe that only 10 years ago, Renee's red-carpet hair was so tousled and casual.

Renee Zellweger, 2008

Oops, she did it again — this time at the 2008 Academy Awards, showing up with a similar messy hairstyle.

Andie MacDowell, 1993

Andie's flapper style is a bit too literal for me. When you're borrowing from another decade, err on the side of simplicity.

Andie MacDowell, 1999

Yes, those are red flowers in her hair. Again, keep it simple. One flower would have sufficed.

Angelina Jolie, 2001

Back in 2001, Angelina still liked the nude-lip look she typically wears now. But without her signature eyeliner, her face looks washed-out.

Annette Bening, 2005

I love Annette Bening, but this orangey lipstick shade and punky hair doesn't work with her features.

Jessica Biel, 2007

Jessica shows why it's not wise to match your lipstick and blush to your dress.

Jon Bon Jovi and Dorothea Hurley

A good rule of thumb, Jon: If your hair has more volume than your date's, it might be time to hang up the crushed-velvet jacket and try again.

Cameron Diaz, 2007

I'm split on Cameron's look here. If anyone can pull off a messy-sexy hairstyle like this one, she can. But it would have stood out more with blond hair, no?

Celine Dion, 1999

Yes, Celine is wearing a white-satin suit. Backwards. While her sleek, long ponytail is pretty, the hat just ruins it all.

Charlize Theron, 2005

Love Charlize's lashes, but her hair's stiffness ages her look.

Cher, 1986

There are no words.

Cher, 1988

...and two years later, still no words.

Cher, 1998

Oh, I give up. Let's see who's next, shall we? Moving along...

Not Cher, 1996

When your dress is as bright as Daisy Fuentes's, it's best to stay away from pastel makeup.

Jane Fonda, 1982

It was the '80s. Large hair ruled. What else can you say?

Debra Winger, 1982

The back of this updo looks lovely, but the curls on top are reminiscent of Flock of Seagulls.

Diane Keaton, 1978

I love Diane Keaton. I love Diane Keaton's androgynous style. I do not, however, love this hairstyle on her.

Diane Lane, 2003

This certainly isn't the worst look in the bunch, but loosening those curls would have softened Diane's look.

Dolly Parton, 1981

Whoa, that's a lot of hair.

Drew Barrymore, 2005

The cool-toned colors on Drew's eyes and lips compete with her warm auburn hair.

Drew Barrymore, 1989

Aw, Drew's hairstyle was so fashionable back in the day. Sadly, so was her date Corey Feldman's mullet.

Ethan Hawke, 2005

Ethan's awkward bangs could have used a trim. Some quality one-on-one time with his Norelco might have also helped make him look more formal.

Eva Green, 2007

Eva's look is a classic example of why less is often more. When you have beautiful brunette hair like Eva's, you can still wear dark colors on your face — but use a light hand with application.

Halle Berry, 1996

Halle made a rare misstep in 1996 when she wore lip liner that was darker than her lipstick.

Helena Bonham Carter, 1987

Oh, Helena. Where to begin...

Jennifer Grey, 1988

Jennifer's spiral perm was considered the coolest hairstyle of the late '80s.

Also, nobody puts Baby in a corner.

Jennifer Hudson, 2007

Jennifer's imbalanced hairstyle and drawn-on brows are too theatrical for my tastes.

Jennifer Lopez, 2006

It's often difficult to wear such a tight bun. Leaving a few wispy tendrils loose would have softened Jennifer's look.

Jennifer Lopez, 1998

The hair is nice, but Jennifer committed the ultimate '90s beauty sin: Brown lip liner with light lipstick.

Jodie Foster, 1993

Jodie could have turned down the volume, so to speak, and let her hair rest more naturally.

Juliette Lewis, 1992

Remember this style and the hullabaloo it created?

Kelly LeBrock, 1985

I usually don't like to poke fun at cheesy old hairstyles, but after she made this annoying commercial [3], I think Kelly LeBrock's huge hair is fair game.

Kiefer Sutherland, 1989

Kiefer could have done the facial scruff or the mullet, but pairing the two was not the best decision.

Kirsten Dunst, 2007

Here's another look that has me torn. Do you think it works on Kiki?

Laura Linney, 2005

Laura sports beautiful makeup, a lovely smile, and — unfortunately — a little too much gel in her hair.

Madonna, 1998

The queen of reinvention went with a tough-yet-ethereal style. But the violet shadow, strong lips, and ringlets just didn't work well together.

Morgan Fairchild, 1982

Before she was a spokesperson for Old Navy, Morgan made some unfortunate hair choices.

Rebecca deMornay, 1986

It seems that Rebecca may have shared a hair stylist with Morgan Fairchild.

Scarlett Johansson, 2005

If you don't remember this, it's because Scarlett was at the scientific and technical Academy Awards. Apparently, she thought a Vanilla Ice-style coif would wow the crowd.

Sharon Stone, 1994

Sharon's look was more appropriate for a funeral than for a celebration like the Oscars.

Sarah Jessica Parker, 1993

Without her gorgeous curls, SJP just doesn't look like herself.

Sarah Jessica Parker, 1995

Sarah Jessica's curls are beautiful, but the violet hues of her makeup aren't as flattering as her current look.

Taryn Manning, 2005


Tom Cruise, 1994

Tom's alterna-guy style didn't stay around long, fortunately. Even Emma Thompson seems a little embarrassed by it.

Winona Ryder, 2001

Later in the year, Winona would be arrested for shoplifting, but in early 2001, she merely committed a crime of hairstyling.

Calista Flockhart, 2008

You gave the thumbs up on the Grecian-inspired dress [4], but the thumbs down on the hairstyle [5].

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