Fame10 Fashion Evolution: Jessica Chastain

Published on January 19, 2015. Updated April 5, 2017

Being fashionable on the red carpet hasn’t always been easy for Jessica Chastain. When she was first starting out in Hollywood, she made some pretty disappointing style choices. It was like she wanted to look sophisticated, but she wasn’t sure how. Since she established herself as an in-demand actress, her fashion has changed considerably. She’ll channel old Hollywood glam at one event and she’ll do sexy, but elegant at another. We love how much her style has changed! Even though she has a much better idea of how to dress now, she doesn’t always get it right. Let’s take a look at her fashion evolution to get a sense of her best and worst style moments!

Jimmy Choo for H&M Shoe Collection Launch Party – 2009

Jessica Chastain looked a bit like an amateur at the Jimmy Choo for H&M Shoe Collection Party. She wore a pair of black skinny pants with a blue ill-fitted tank top. We can’t even tell if the pants are good or bad because we can’t take our eyes off of this ugly blue tank top. It hides everything, including her slim frame. We think that this would be perfect for someone who is pregnant or slightly overweight, but not for someone with a hot body.

We think the reason that she was so unstylish at this point had to do with the fact that her career hadn’t really taken off. She had just graduated from television to movies; however, she had yet to have a big critical or commercial hit. According to her, she had trouble at the beginning of her career just getting jobs because of her unconventional appearance.

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Decades Denim Launch Party – 2010

The budding actress tried to go for a more sophisticated look at the Decades Demin Launch Party. She wore this knee-legnth ivory dress, which was trying to do too many things at once. It looks as though it was only supposed to consist of a strapless dress portion, but then someone decided to add sleeves and a back to it. The black belt is a nice touch, as are the black pumps; however, we’re not so sure about the green clutch. We’re not even sure if someone styled her for this event. If someone did, they are not cut out for the styling business.

Jessica Chastain was still waiting for her career to take off at this point. Like many other actresses who have been in this position before her, she was particularly unfashionable before she joined the A-list. She was just waiting for her breakout role while we were waiting for her to get it right on the red carpet.

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Natural Resources Defense Council’s Oceans Initiative – 2011

Jessica Chastain attended the Natural Resources Defense Council’s Oceans Initiative looking like a little more thought and care went into her hair and clothes. While we love the way she’s styled her hair, we do have some issues with her ensemble. The dress itself isn’t bad. It fits her reasonably well. The shoes don’t fit though. They are a bit too clunky for the dress. Also, closed toed pumps would have been a better choice.

On the plus side, our favorite redhead was just becoming a real star at this point, which was pretty exciting! She appeared in “The Help,” which got her an Academy Award nomination, as well as “The Tree of Life,” alongside Brad Pitt, the crime thriller “Texas Killing Fields” and “Take Shelter.” “The Help” was by far her biggest commercial success. Although she didn’t win the Oscar for her performance, her name and face were now impossible to forget.

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84th Annual Academy Awards – 2012

At the 84th Annual Academy Awards, the redheaded actress looked amazing. She had been nominated for the Best Actress Oscar that night for her role as a simple but kind-hearted southern housewife in “The Help.” We really think that she knocked it out of the ballpark with this ensemble. She donned a regal-looking black strapless Alexander McQueen gown, designed by Sarah Burton, which featured gold and black embroidery and tumbling tiers of silk organza. She didn’t take home the Academy Award that night, but she did end up on countless best dressed lists thanks to this daring number.

We think 2012 was one of the biggest and best years for Jessica Chastain. After years of struggling as an actress, she finally got her big break. In addition to her Oscar nomination, she had also received a Golden Globe nod. It may have been a slow road to success, but we think that it is fair to say that she has finally arrived.

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Lawless Photocall at the 65th Annual Cannes Film Festival – 2012

Jessica proved yet again how fashionable she can be at the photocall for “Lawless.” She wore this V-neck dress from the Fall 2012 Herve L. Leroux collection, which featured a multicolored top and a black pencil skirt. She completed her look with open toed Giuseppe Zanotti slingbacks and a cute little braid running through her hair. Overall, we like this look. The only thing we would change are the shoes. Black closed toed heels would have been better.

That same year, Chastain showed us just how far she’s come since her days as an actress struggling for recognition. Time magazine chose her to be on their list of the 100 most influential people in the world and she was also invited to join the Academy of Motion Picture Arts and Sciences. In addition, Yves Saint Laurent chose her to be their ambassador for their fragrance, Manifesto. She was officially A-list!

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British Academy Film Awards – 2013

“The Help” star rocked the red carpet at the British Academy Film Awards. She stunned in this structured sapphire gown by Roland Mouret, which featured an asymmetrical bodice, and Harry Winston pendant earrings and a simple bracelet. This is probably one of our favorite looks of hers yet. The blue really warms her skin tone and provides a nice contrast with her strawberry-colored hair. If she could consistently dress like this on the red carpet, we would be forever grateful.

At this point, Jessica Chastain had established herself as an in-demand actress. She was reportedly offered the role of Princess Diana in the biopic film, “Diana,” but dropped out, which is why it went to Naomi Watts. This same year, Chastain received her second Academy Award nomination for Best Actress for her role in “Zero Dark Thirty.” Again, she didn’t end up winning, but she took home the Golden Globe for her performance.

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amfAR’s 20th Cinema Against AIDS Gala – 2013

Jessica looked ravishing at amfAR’s 20th Cinema Against AIDS Gala. She wore this asymmetrical maroon-colored Saint Laurent by Hedi Slimane gown, which featured a cut-out detail just under the bust. She completed her look with a Bulgari serpent bracelet and styled her hair in lose waves. Whoever said that redheads shouldn’t wear red has obviously never seen Chastain. She can pull red off like no other redhead in Hollywood.

When it comes to her looks, this Golden Globe-winning actress hasn’t always been that confident. “I don’t see myself as the face that launched a thousand ships,” she told The New York Times back in 2013. “There are things I didn’t like about my look when I was growing up; I wanted to be the pretty girl with the curly blond hair and the tan skin.” That is a classic line for women – we always want what we don’t have!

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Photocall for The Disappearance of Eleanor Rigby – 2014

The Academy Award-nominated actress attended the photocall of “The Disappearance of Eleanor Rigby” in this sleeveless Alexander McQueen Fall 2014 velvet jacquard black dress, which featured a leaf pattern. She accessorized with pink-embellished Paul Andrew shoes. Mixing patterns is a pretty bold move, but we think it works in this particular situation. The black dress needed something to liven it up and the shoes were the perfect accessory to do that!

The film, “The Disappearance of Eleanor Rigby,” sounds pretty interesting. It consists of three films, one told from the man’s perspective; the second from the women’s; and third is a combination of both. Jessica Chastain’s ex, Ned Benson, is the one who wrote it especially for her. These two broke up back in 2010 and filmed it in 2012. These two sound like they are on pretty good terms. There aren’t many exes in Hollywood who would have collaborated after a breakup.

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72nd Annual Golden Globe Awards – 2015

Jessica Chastain channeled old Hollywood glam for the 72nd Annual Golden Globe Awards. She donned this shimmering and smoldering bronze Atelier Versace halter gown, which provided a great contrast with her pale skin. Even though she was nominated for the Best Actress award for her role in “A Most Violent Year,” the talented actress went home that night empty handed. The Golden Globe nod was the only real nomination she received this year. The Academy Award, BAFTA and the Screen Actors Guild all snubbed her.

We don’t think she’s losing any sleep over it though. “Thank you all for the love! I’ve had the opportunity to be in 4 films this year that I’m really proud of. That is enough for me,” Chastain tweeted, following the Oscar nominations announcement. Hopefully she’ll still attend all of the awards shows. We really want to see what red carpet looks she’ll rock next!

Photo by David Fisher/REX (4366459ad)

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