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16 Best, Worst and Iciest 2014 Oscars Fashion Moments

From Karen O’s stunning gowns to an overabundance of silvery embellishments, ranking the red carpet

Lupita Nyong'o amy adams oscars

Kevin Mazur/WireImage; Steve Granitz/WireImage

Though it's Hollywood's foremost evening of glitter and glamour, we regret to note that the 86th Annual Academy Awards followed suit in the red carpet march towards classy monotony — imagine there ever being a moment as wonderfully unexpected as Bjork's Marjan "KTZ" Pejoski swan dress, or Cher's  iconic Bob Mackie gowns in 2014? It's a shame. The age of the professional stylist, on one hand, has helped some stars dress better and more sleekly; on the other hand, it's wiped out a lot of the risks and/or originality that individuals might venture on their own. Still, there will be highlights and low lights at any black tie event, regardless of the adventurousness of its attendees. Here are the best and the worst of them. By Julianne Escobedo Shepherd

See all our 2014 Oscars coverage here!

Pharrell Williams Helen Lasichanh Oscars

Steve Granitz/WireImage

BEST: Pharrell Williams and Helen Lasichanh

Skateboard P neglected to don The Hat Heard Round The World™ until later in his performance of "Happy," in which he once again took a cue from Malcolm McLaren's "Buffalo Gals" video look and stomped around in ruby sneakers. But for the red carpet, he opted for super-cool shortpants with his tuxedo, going sockless and making all the longpants-wearers look stiff and fussy. That is, except his wife Helen Lasichanh, who wore a tuxedo suit that complimented his look, chic yet official. (We would have opted for a different shoe, though.) Well played, Shortpants P.

karen o oscars

Jason Merritt/Getty Images; Adam Taylor/ABC via Getty Images

BEST: Karen O

Karen O on a red carpet is where she damn belongs, if this gown is any indication: custom designed by Camilla Staerk and Brandy St John, she is straight-up a 1930s silver screen goddess, something like Loretta Young meets Clara Bow. Has anyone ever discussed her cheekbones, also? You could cut a diamond on those things.

But Ms. O never looks more comfortable than onstage, and her performance in this crimson cloud of a gown came straight from a dream sequence (with Vampire Weekend's Ezra Koenig by her side in matching socks). Karen O's stage costumes have been designed by friend and collaborator Christian Joy since the beginning of her career, and this was no different — but it showed how truly talented Joy is across the board, able to dream up high-concept looks as easily as gorgeously floaty night gear. Tens all around.

kerry washington oscars

ROBYN BECK/AFP/Getty Images

BEST: Kerry Washington

This woman is hella pregnoncé and at that point, you wanna a give a woman a pass for wearing whatever she damn well pleases. Wear a Snuggie on the carpet, boo, no one's gonna be mad at you. Holla if the water breaks. But Kerry Washington is an impeccable dresser, and she wouldn't let a mountain of baby get in the way of that: Jason Wu crafted this gorgeous gown especially for her and her seed, allowing for give and comfort in the most perfect shade of dusty purple she's ever worn. It got a little wet at the bottom — the carpet was thick with rain — but she worked it like a runway champ.

Stacy Keach wife Malgosia Tomassi Oscars

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BEST: Malgosia Tomassi

Interior designers tend to have the best exteriors. Iris Apfel, anyone? Malgosia Tomassi, who is also a former model and actress, showed up with her husband Stacy Keach looking like an Italian fashion editor and stunting on virtually everyone else on the carpet. One-inch heel? Yup. Checkerboard sunglasses like "don't look into my eyes"? Mmm-hmm. Ruffled blouse, untucked? Whatever. Welcome to her world, wherein she is completely unbothered.

Lupita Nyong'o oscars

Kevin Mazur/WireImage

BEST: Lupita Nyong’o

What more can possibly be said about this lovely, classy human? She is a goddess and here is the picture that proves it: even the wind bends to her beauty. Custom Prada gown, in an icy shade that she called "Nairobi blue." Headband like a tiny crown. She dresses like the Oscar winner she is every time. She is one with the clouds. LUPITA.

Liza Minnelli Oscars

Kevin Mazur/WireImage

BEST: Liza Minnelli

There are certain technical issues with this ensemble: the cut and draping are not quite right, the pantseams are a little too obvious, it's unclear whether the material is flammable and we probably wouldn't have worn a black boot underneath. But it's also a perfect example of what we need to see more of on red carpets everywhere: A PERSON being A PERSON, rather than A PERSON being STYLED as A PERSON. Liza is so herself at every moment and she looked FABULOUS, especially with her matching blue lock. During the ceremony she asked Ellen if she liked the blue in her hair, and we hope she could heard us screaming "YAAAAS" from our couch in New York City.

meryl streep oscars

Steve Granitz/WireImage

BEST: Meryl Streep

The queen bee generally goes with this type of neutral color palette, because she knows what works for her and she is a boss. The off-the-shoulder look is an added note of vavoom, though. We know that's a clutch she's holding, but it looks like reading material and we like to imagine her heading off to her book club after the ceremony, like, bye.

Cate Blanchett oscars

Steve Granitz/WireImage

BEST: Cate Blanchett

Cate is one of the few Hollywood stars who is sartorially adventurous, and we're really glad she came dressed as her Lord of the Rings character this year. It's like Galadrial summoned all the ice crystals in Elventowne to charm her gown. Ice crystal was actually a running theme at this year's Oscars, but more on that in a bit.

John Legend Christine Teigen oscars

Steve Granitz/WireImage

BEST: John Legend and Chrissy Teigen

Chrissy Tiegen is a walking cherry blossom in this guy by Monique Lhullier, while John Legend cuts a striking beau in a traditionally cut tux. Full class.

Will Smith Jada Pinkett Smith Oscars

Steve Granitz/WireImage

BEST: Will Smith

Big Willie Style's cravat and pocket square were what you'd expect from an aging gentleman of Hollywood, and our biggest wish is that he ditched the afterparties to down a snifter of 45-year-bourbon at a cigar bar afterwards. If the Dos Equis guy ever retires, we know a certain Fresh Prince who could replace him.

amy adams oscars

Steve Granitz/WireImage

WORST: Amy Adams

In our heart of hearts, we want to love this Gucci jam, but on TV the material read as some kind of polycotton blend (or RAYON), while the folds had the effect of Amy as a marmish secretary via Joan Holloway, minus sex. Do not want.

portia de rossi

Kevin Mazur/WireImage

WORST: Portia de Rossi

Not against this cutout Naeem Khan gown in theory,  but it washed-out Portia with the added bonus of looking like someone's dinner setting (which made us hungry).

kate hudson oscars

Steve Granitz/WireImage

WORST: Kate Hudson

YES she is gorgeous and YES she is going for Veronica Lake and mostly succeeding, but girl, the caping is just a little too drapey not to invoke a DC Comics character. Up, up, and away, my dudes.

angelina jolie

Steve Granitz/WireImage

WORST: Angelina Jolie

This year's ad hoc red carpet theme was icy looks and silvery embellishments, but Angie's gown took it a step further into what we like to call "boob icicles." The gown was gorgeous but proportionally not doing it for her, and via HDTV came off like Christmas tinsel.

lady gaga oscars

Kevin Mazur/WireImage

WORST: Lady Gaga

Might have been fine without the cape but there's something try-hard about it, plus she was giving us lacefront realness. Wait, why was she here again? Oh right, she's joining Kate Hudson's superhero gang. Get it, girls.

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