We’re Revisiting Our Favorite Oscar Looks (And Fails)

On February 8, the Academy will announce its official nominees for 2022 Oscars. To celebrate the start of another Oscar season, we’re revisiting our favorite Oscar looks (including a few that we love to hate).

From Cruz to Kidman: Our All Time Top Five

5. Nicole Kidman, 89th Academy Awards (2017)

(Frazer Harrison/Getty Images)

Nicole Kidman has worn many amazing red carpet looks. But in this writer’s humble opinion, one of her best was at the 2017 Oscars. Her already-stunning frame was enhanced by her column-length bejewelled dress. The fabric had the most delicate cream and peaches colors that perfectly matched her fair skin.

Kidman’s 2017 look embodied the art deco flair of the 1920s with a modern silhouette. Her makeup and accessories were minimal, leaving the dress to speak for itself.

4. Penelope Cruz – 79th Academy Awards (2007)

Penelope Cruz wearing pink feathered ballgown on red carpet
(Frazer Harrison/Getty Images)

I’m not exaggerating when I say this dress has been on my mind since I first saw it in 2007. I’m not even a mega-fan of Penelope Cruz, just this one specific dress she wore 15 years ago. This dress is the epitome of dreamy romance, from its dusty rose hue to the dramatic, feathered skirt.

This dress has kept my attention for longer than most of my relationships. Versace must have been thinking of this. Something right.

3. Lauren Hutton, 47th Academy Awards (1975)

Lauren Hutton in rainbow dress and fur
(Michael Ochs Archives/Getty Images).

Speaking of outfits withstanding the test of time, few Oscar looks compare to the effortless glamour of model Lauren Hutton’s 1975 ensemble. Her honey-blonde blonde hair and sun-kissed skin made the pastel colors of her Grecian dress pop. She wore a plunging, luxurious fur over it because it was 70s.

Countless others have. imitated Hutton’s look since then, and honestly, they’ve all killed it. It’s pretty easy to do when the gown does all the heavy lifting.

2. Zendaya, the 87th Academy Awards (2015)

Zendaya in white gown and dreadlocs on red carpet
(Jason Merritt/Getty Images)

If they made a Barbie doll after your Oscars look, then you know you must’ve hit the mark. Zendaya did just that with her 2015 Oscars look. Her effortless look combined modern elegance and simplicity. She also styled her hair with a sleek, sleek look that included subtle teardrop earrings and a silver cuff.

It’s hard to pick a favorite of all of Zendaya’s red carpet looks. This ensemble is the best, at least for the moment.

1. Lupito Nyong’o: 86th Academy Awards (2014)

Lupito Nyong'o in blue dress on red carpet
(Robyn Beck/AFP via Getty Images)

Lupito Nyong’o crushed the 86th Annual Academy Awards, period. Her first feature film, 12 Years as a SlaveShe won a staggering nine Oscars. In a delicate, powder blue Prada gown, she wore an equally stunning Prada gown. This stunning gown, with its plunging neckline, and simple banded waist, is number one in my Oscars best of book.

Nyong’o’s Prada ensemble is the epitome of modern-day Cinderella. All it’s missing is a black choker and puffy sleeves, but I vote that Nyong’o’s version is better.

From Goofy to Goose-y: Our Top Failed Attempts

5. Barbara Streisand: 69th Academy Awards (1997)

Barbara Streisand in gold glittery outfit on red carpet waving to someone off camera
(Vince Bucci/AFP via Getty Images

No disrespect to Streisand, but her 1997 Oscars ensemble landed her on the “worst-of” list. There’s a lot to unravel with this piece. The glittery crochet cardigan wrapped around her shoulders is a good option. Maybe we can opt for the stretch knit dress. You might also like the slouchy crochet handbag.

Every article of glittery, droopy knits is a neutral gray-beige. We love you, Babs, but there’s not enough glitter in the world to hide this fail.

4. Kerry Washington: 88th Academy Award (2016)

Kerry Washington in white and leather gown on red carpet
(Kevork Djansezian/Getty Images)

Sometimes simplicity is the best. Indeed, Kerry Washington’s 2016 Oscars look proves this point beautifully. There’s no denying that Washington looks stunning in almost anything she wears. But there’s something about this stark white skirt and leather bodice combo that seems disjointed and rushed.

Is she raiding a tomb Lara Croft style or walking the red-carpet? We don’t know. Let’s just chalk it up to 2016 being a weird year.

3. Sarah Jessica Parker: The 82nd Academy Awards (2010)

Sarah Jessica Parker in yellow silk gown on red carpet
(Alberto E. Rodriguez/Getty Images)

Sarah Jessica Parker is a fashion icon. She blazes trails and sets trends, which means she’s bound to have a few misses every once in a while. One such failure was her pale yellow 2010 Oscars dress. The dress is passable if viewed at the right angle. It is a bit sloppy and unmatched from the rest of the pictures.

The yellow shade complements Parker’s eyes and hair color. Still, I can’t get past the tin foil feature across her chest. It still baffles and puzzles me 12 years on.

2: Bjork: 73rd Academy Awards (2001)

Bjork goose dress
(Lucy Nicholson/AFP via Getty Images).

Is it possible to have an Oscars Look Roundup? WithoutBjork? You are familiar with this dress. You’ve likely seen it a million times since its first feathered debut in 2001–both in real and spoof forms. Why? wouldn’tDo we still remember the goose gown from 20 years ago? Do you know of any other swan dress that could take its place?

Of course, you don’t. This dress is as unique as Bjork. It is a symbol of Y2K pop culture, in all its downy glory.

1. Lisa Rinna, 81st Academy Awards (2009)

Lisa Rinna in purple gown on red carpet
(Kevork Djansezian/Getty Images)

Lisa Rinna was the final. Look, I’m fully aware that the mid-2000s was a dark time in fashion’s history. I can attest to this with the gauchos as well as the oversized belts. But there’s something timelessly terrible about Rinna’s 2009 Oscars outfit. This ensemble shrieks “2009” from top to bottom in the worst possible way.

With her chunky, curly ‘do and asymmetrical gown, Rinna could have just as easily been attending a wedding as a bridesmaid in 1988. It shows that celebrities are not immune to the fashion disasters of 2000s.

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