Oscar Fashion Report Card

Penélope Cruz

The greatest red carpet sin is to be boring. Too often, starlets in pursuit of “old Hollywood glamour” play it safe—and dull—in bias-cut silk or yards of tulle. Tonight, we’ll review Oscar fashion the way they judge diving at the Olympics, with extra points awarded for degree of difficulty. Cruz didn’t try anything fancy here, and the look is blah as a result—justly dismissed by some on my couch as a “stupid princess gown.” The color is nice, though.

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J. Lo

This spangled extravaganza would be great—but for the sleeves, which featured oddly shaped openings that looked like sausage casings split by the heat of the griddle.
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Emma Stone

Nicole Kidman wore a dress with a gigantic red bow at the neck a few years ago—and though I wasn’t a fan, the look suited Kidman’s stilted, stiff persona. (The bow made her look animatronic, a torso with a head tied on.) Stone is such a loose and lovely actress that she almost pulls this off, and she gets points for the bold red color, but the dress is too big, and the bow is simply too enormous and unwieldy.
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Kristen Wiig

I like the idea of Wiig’s casual, beachy hair and low-key jewelry—she has a dynamite green ring on—but I can’t get over the blah color and the fact that this dress looks a bit like a haystack. Or a thatched roof.
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Sandra Bullock

There was a lot of lovely jewel-encrusted ornament on Oscar gowns this year—but the detail on the waist of Bullock’s dress looks sinister, like sparkly seaweed hands reaching for her belly.
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Judy Greer

Greer gets points for trying something new—and for keeping up with the scuba trend in fashion this year—but there’s something about the black panels on the sides that look a bit Land’s-End-mom-bathing-suit. You don’t need slimming panels, Judy Greer!
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Bérénice Bejo

Bejo should have had a French style-confab with Oscar couture goddess Marion Cotillard, who always manages to look glamorous, unusual, sexy and low-key in a fabulous French way. I wanted to like this, and I tried to decide the mint bugle beads were somehow effortlessly Parisian—but I think it looks a little mother-of-the-bride.
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Melissa McCarthy

It is impossible not to be charmed by everything Melissa McCarthy does, but this is not the most flattering dress she’s worn this awards season. The deep blues and greens she has been sporting are more flattering than this washed-out plum.
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Viola Davis

The color is gorgeous. The earrings are gorgeous. The fit is gorgeous. The décolleté is glorious. The skirt is covered in strange pleated frippery and has a giant rip the shape of a pea pod in it.
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Maya Rudolph

Rudolph’s clothes always fit perfectly. The cap sleeves are saucy and fun.
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Rose Byrne

How does one make head-to-toe sequins looks slouchy, modern and cool? Byrne pulls it off, in part because of this dress’s chic draping and stylish back.
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Octavia Spencer

This dress is a lesson in fit. The draping could not be more perfect or flattering, and I love how the stripes in the beading complement the cut. I don’t even mind the muted color—this just looks right on her.
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Tina Fey and Michelle Williams

I guess the peplum really is back! Michelle Williams’ bold fiery red dress looked stunning, and the peplum gave some shape to her frail frame. Fey looks classic and elegant in her navy number, and the peplum is flattering. (Her bun, though, was epically proportioned—approaching volleyball-size!)
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Glenn Close

I love Close’s forest-green tuxedo-gown combo. It’s nice to see a mature actress collaborating with a hip young designer like Zac Posen, and the resulting look is flattering, cool, and interesting.
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Gwyneth Paltrow

Paltrow’s Oscar fashion has been getting chicer by the year, and I enjoyed her slim, built-in cape, which made her look like the high priestess of a futuristic sect I don’t care to join—but in a good way.
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Shailene Woodley

This dress had its detractors—but I loved it. It was unexpected and mod—Woodley looked like a hot bride at a ‘60s wedding. The details were impeccable—particularly the drape of the shoulders and the sleeve. I’m excited to see what she wears next.
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Milla Jovovich

Jovovich looked stunning. The aggressive shoulder and unusual draping save this from being a boring, “old Hollywood glamour” retread, and it moved beautifully when she walked.
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Ellie Kemper

What a knockout! Ellie Kemper looked stunning—like a really happy and friendly Jessica Rabbit—in this auburn sequined number that perfectly matched her hair. This was one of the top looks of the night.
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Jessica Chastain

My favorite detail of this stunning black and gold McQueen gown was the little chains stitched into the gold brocade on the skirt—a rock-and-roll touch on this very regal look.
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Rooney Mara

The best Oscar gown in ages. The cobwebby quality of the tulle, the arched architecture of the bust, the detailing on the deep back: All unusual, and all lovely on Rooney Mara. She may be a little inert in interviews, but her red lip kept things fun. The dress was surprising, intriguing, and flattering—just what an Oscar dress should be.
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