Predict-a-Gown: What Will Oscars Stars Wear?

Play celeb stylist and guess which of these runway looks Jessica Chastain, Angelina Jolie and more will don on Hollywood's biggest night

01 of 26

JESSICA CHASTAIN

JESSICA CHASTAIN
Kevin Mazur/Wireimage

There’s always something nontraditional about the gowns the Best Supporting Actress nominee chooses, whether it’s a funky shade or a unique pattern.

02 of 26

OUR PREDICTION

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Frazer Harrison/Getty; Brian Ach/Getty

The redhead may continue her metallic streak and go with a golden-emblazoned Naeem Khan. She loves green, though, and this pea-colored Carmen Marc Valvo cutout creation would look great on her slender frame.

03 of 26

ANGELINA JOLIE

ANGELINA JOLIE
Dimitrios Kambouris/Wireimage

Look for something classic with an Old Hollywood feel from , who will present an award and play the role of Best Supporting Significant Other to Best Actor nominee .

04 of 26

OUR PREDICTION

OUR PREDICTION
Fernanda Calfat/Getty; Frazer Harrison/Getty

Angelina could choose a glittering gold confection by Venexiana in one of her favorite silhouettes or she could return to her long-sleeve roots and pick this sheer Tadashi Shoji.

05 of 26

MICHELLE WILLIAMS

MICHELLE WILLIAMS
Kevork Djansezian/Getty

Floral and feminine is the name of the game for , who’s turn in My Week with Marilyn earned her a Best Actress nod.

06 of 26

OUR PREDICTION

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Fernanda Calfat/Getty; Frazer Harrison/Getty

Jason Wu’s striking red number fits all of Michelle’s requirements: cap-sleeves, high neckline, a touch of floral. But the star has been changing up her style lately, so she could go for this black-and-white sleeveless Naeem Khan frock.

07 of 26

VIOLA DAVIS

VIOLA DAVIS
Gilbert Flores/Celebrity Photo

The necklines, silhouettes and accessories change, but one thing stays the same when it comes to the Best Actress nominee’s red carpet style: bright colors. She always chooses standout hues, from shimmering white to hot pink.

08 of 26

OUR PREDICTION

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Dario Cantatore/Getty; Julien Hekimian/Getty

The Help star has done just about every shade of pink and red, which leaves an orange gown – like this Juan Carlos Obando – as an obvious choice. But we could also see her in a greenish-yellow, one-shoulder Christophe Josse.

09 of 26

SHAILENE WOODLEY

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Kevin Mazur/Wireimage

The Descendants starlet has made it clear she doesn’t care about fashion, so expect a dress with a simple cut that’s easy to wear – in one of her favored neutral shades like blush, off-white, pink or peach.

10 of 26

OUR PREDICTION

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Frazer Harrison/Getty; Pascal Le Segretain/Getty

Shailene may pick a J. Mendel number with delicate detailing that hugs her slender frame or an A-line Elie Saab with the floral embellishments she so clearly likes. (Both would hide a pair of barefoot running shoes too!)

11 of 26

KRISTEN WIIG

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Rachel Kelly/Photo Image Press

Bridesmaids’s leading lady almost always opts for cleavage-baring, deep-V necklines, and after her SAG Awards choker-halter fashion fiasco, we think she’ll stick to a basic silhouette with minimal accessories.

12 of 26

OUR PREDICTION

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Frazer Harrison/Getty (2)

Kristin can’t go wrong with a flowing black Dennis Basso gown, but she may decide not to play it quite so safe and wear this liquid metallic Naeem Khan creation that will drop jaws (in a good way).

13 of 26

PENéLOPE CRUZ

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Gregg DeGuire/PictureGroup

The actress, who will be a presenter on Sunday, loves structured gowns with a lot of wow factor, and she’s a sucker for the color red.

14 of 26

OUR PREDICTION

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Neilson Barnard/Getty; Arun Nevader/Getty

Penélope wore Donna Karan in 2010 and ended up on a number of best-dressed lists, so she may try to repeat her style success with a black-and-white dress by the designer. If she goes with red, though, this Lorena Sarbu would be a perfect fit.

15 of 26

HALLE BERRY

HALLE BERRY'S MAKEUP
Steve Granitz/WireImage

One thing’s for certain: Whatever gown the (and presenter) chooses, it’ll be sexy and spotlight-stealing. Expect a look that shows a lot of skin or turns heads thanks to a vibrant jewel tone.

16 of 26

OUR PREDICTION

OUR PREDICTION
Victor Boyko/Getty; Clary/AFP/Getty

We’d love to see Halle go for the gold in a plunging Zuhair Murad or look pretty in hot pink (a hue she’s favored in the past) by Ralph Lauren.

17 of 26

ROSE BYRNE

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Dimitrios Kambouris/Wireimage

Also presenting an award Sunday, the actress is sure to select a dress that pairs with her Scarface-inspired bob, so be on the lookout for something ’70s and funky.

18 of 26

OUR PREDICTION

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Frazer Harrison/Getty (2)

Michael Kors’s sparkly red frock is like the glam, Oscar version of Rose’s SAG Awards jumpsuit, but Rose would also look ultracool in a golden Ralph Lauren halter with a pleated bodice.

19 of 26

ROONEY MARA

ROONEY MARA
Villard/Sipa

A Best Actress nominee for her role in The Girl with the Dragon Tattoo, Rooney is partial to edgy designs in black or white with cutouts.

20 of 26

OUR PREDICTION

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Victor VIRGILE/Gamma-Rapho via Getty; Frazer Harrison/Getty

One of Rooney’s favorite designers is Prabal Gurung and this dress, from his latest collection, seems to practically be made with her in mind. The same goes for Falguni & Shane Peacock’s cap-sleeve, sheer creation.

21 of 26

JENNIFER LOPEZ

JENNIFER LOPEZ
Jason LaVeris/FilmMagic

When the steps on stage to present, she’ll most likely be wearing something that reveals a lot of skin and hugs her famous curves.

22 of 26

OUR PREDICTION

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Fernanda Calfat/Getty; Frazer Harrison/Getty

J.Lo could make a dramatic entrance in a black Jason Wu gown with a high slit, or shock and awe the audience by donning a cutout Reem Acra that leaves little to the imagination.

23 of 26

SANDRA BULLOCK

SANDRA BULLOCK
Stephen Lovekin/Getty

The , whose movie Extremely Loud & Incredibly Close is up for Best Picture, doesn’t have one signature style, instead wearing a variety of looks that range from vintage-inspired and frilly to modern and bright.

24 of 26

OUR PREDICTION

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Richard Bord/Getty; Mike Coppola/Getty

No one would be surprised if Sandy went with a lemony-yellow frock that showed off her décolletage, like this Basil Soda design, and we also see her walking the red carpet wearing this ’20s-esque Badgley Mischka.

25 of 26

KATIE HOLMES

KATIE HOLMES
Vince Flores/AFF-USA

Her will be presenting an Oscar, so will probably be on hand in something timeless that shows off her body and her unique taste in style.

26 of 26

OUR PREDICTION

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Arun Nevader/Getty; Slaven Vlasic/Getty

Designer Lorena Sarbu’s long-sleeve creation in silver and black has Katie’s name all over it, but she may decide to go the sexy route and flaunt her assets in a Sachin + Babi double-slit, quadruple-strap stunner.

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