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Oscar Fright: The Top 10 Worst Red Carpet Looks, 2000-2009

21 January 2010 No Comment

And now it’s time to pay tribute to the gowns we really love: the egregious missteps in the name of fashion that make us cover our eyes and shriek aloud, “Girl, what are you wearing?!” Without them, the Oscars would be boring — what fun is an awards show where everybody looks flawless and nobody takes any risks? It’d be like, well, watching the men of the Oscars parade down the red carpet in their nearly-identical tuxes.

In a way, I have to admire these women. There’s something cool about an actress who, when planning her outfit to wear to the Oscars, thinks, “Should I do a little black dress? A slinky slipdress? Nah, let’s go for a dirndl!”  They may have failed mightily, but at least they failed memorably. And so here are 10 of the most memorable gowns of the ’00’s:

Top Ten Worst-Dressed

10. Angelina Jolie, 2000

On the heels of Jolie’s coruscating performance in Girl, Interrupted, everyone wanted her to wear something edgy and dramatic — not look like an extra from Twilight. Objectively, this dress isn’t too bad — it’s the “too cool for school” attitude Jolie was pulling that makes this look so irritating. She was like that Goth kid back in high school who rolled her eyes when the principal handed out Honor Roll certificates, even though you knew she was secretly glad to get one.

9. Tilda Swinton, 2008

Swinton prefers understated, haute couture-inflected looks, and has established this so firmly as her personal style that it’d be downright weird to see her in, say, a slinky red slipdress. Still, there’s good couture and bad couture, and this shapeless bag of a dress definitely falls in the latter category. It reminds me of nothing so much as Armus, the oil slick with a bad attitude from “Skin of Evil,” one of the worst Star Trek episodes of all time.

8. Anne Hathaway, 2007

Rarely has one detail so thoroughly ruined an outfit as in Anne Hathaway’s ‘07 gown. Without the outsized bows, it would have a nice, if somewhat bridal-looking dress, but with them, one wonders what she was thinking. The back bow takes the dress to twee levels, and the front one, which registers as a Rorschach pattern rather than a bow, puts it over the top. Fortunately, Hathaway, like Nicole Kidman and Kate Winslet before her, learned from experience and wore a prettier gown in ‘08 and an absolute show-stopper in ‘09.

7. Heather Mills, 2002


This ensemble looks like something your wacky aunt would wear to casino night on a Carnival cruise.

6. Jessica Biel, 2009

Last year, Jessica Biel forgot about the Oscars until the last minute and just put on the first thing she found when she stepped out of the shower — which, alas, happened to be her towel.

5. Jennifer Connelly, 2002

The hemline of Connelly’s droopy Balenciaga looks like it had a run-in with a wood chipper, and that shade of old-lady beige puts me in mind of pantyhose. Some bling would have perked it up a little, but Connelly inexplicably went for a scarf instead. I wish she’d revisited one of her career’s greatest hits and gone in something like this instead:

4. Cameron Diaz, 2000

One good rule of thumb when choosing gowns: If it makes other women cringe in sympathetic pain or embarrassment at what you’ve done to your bosom, it’s a bad gown. This is a bad gown.

3. Kirsten Dunst, 2007

Dunst, 25 when this picture was taken, appears to have raided her grandmother’s wardrobe to find this mother-of-the-bride-style creation. But even a grandma would probably nix the feathers on the hem and the pseudo-Peter Pan collar.

2. Gwyneth Paltrow, 2002

Even Goth or would-be Goth girls (ahem, Angelina) can’t pull off Goth at the Oscars. Cher can, but she’s Cher. When a very non-Goth, nay, an anti-Goth celeb like Gwyneth Paltrow tries to do so, the results are disastrous. This dress is like the sartorial version of a depressive episode.

(Also: See rule of choosing gowns, above.)

1. Uma Thurman, 2004

I can’t make heads or tails of this outfit. Was Uma’s stylist deliberately trying to sabotage her? That’s the only explanation for why she’s got on a dirndl over a oversized work blouse, trimmed with a blue ribbon. This outfit could have worked if only she had tightened up the figure-erasing looseness of the fabric, lost the slit in the skirt, done something about those awful puffy sleeves, and . . . never mind. There’s no fixing this outfit.

The Runners-Up

These gowns might not be as egregious as the 10 listed above, but they come pretty close.

Miley Cyrus, 2009

Miley might have made the top 10 had she not been underage. Really, was there no one around to tell the poor child that, as cute as looking like a Christmas tree sounds when you’re 16, it’s something you’ll regret three or four years later?

Beyonce Knowles, 2009

This is not the best way to advertise your family’s fashion line. I think I may have found the inspiration for this dress, however:

Anika Noni Rose, 2007

Wearing deep cleavage to the Oscars is fine, and going along with the metallic fabric trend is fine, but combine the two and you risk looking too, uh, ‘working girl.’ That or ‘engineering student who made her own dress out of duct tape.’

So Bad They’re Good

And then there are the dresses so outrageous they deserve a category of their own.

Tyra Banks, 2000

Tyra totally indulged her inner child on this one. I imagine her saying, “I want to look like a princess, dammit!” — and when are you going to get to wear this poofy a dress, except at the Oscars or possibly your wedding? — and picking out something from the Glinda the Good Witch collection.

Faith Hill, 2002

Inspired by Toucan Sam, this would be a nice enough dress, were it not for the fact that it’s four different colors.

Dolly Parton, 2007

The crocheting! The chiffon! The baby pink color! The implants! The tiny bow! This dress is pure Nashville cheese, and Dolly knows it, and she just doesn’t care. She had more fun than anybody else on the red carpet that night.

And, finally (you knew it was coming):

Bjork, 2001

Only someone from a country like Iceland, where they still believe in elves and consider months-old rotten shark a delicacy, would think to wear a giant stuffed swan — complete with white, egg-shaped purse — to the Oscars. Is it witty or just weird? Either way, Bjork singly-handedly punctured the pomposity of the Academy Awards with her take on Tchaikovsky.


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