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Jessica Chastain always manages to turn heads with her bold sense of style. Wonderwall.com rounded up her all-time greatest fashion moments, starting with this show-stopper…
Sorry she's not home right now, she's walking into spiderwebs… During the 2023 Golden Globe Awards, Jessica Chastain donned a strapless Oscar de la Renta gown featuring a circular mesh design that made it look as though she'd walked straight into a shimmering crystal spiderweb.
Keep reading for more of her best fashion moments…
MORE: Hall of fame: The worst-dressed stars at the Golden Globes over the years
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Jessica Chastain vamped it up in Versace at the 78th Venice International Film Festival premiere of "Scenes From a Marriage" in Italy in 2021. The redheaded beauty's bold column gown featured streaks of red crystal detailing. And when it came time to accessorize, she tapped Chopard for a stunning diamond necklace.
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Jessica Chastain donned this beautiful blue creation during the 2017 Golden Globes. The powder blue Prada gown featured intricate floral detailing down the left side and paired perfectly with her dramatic diamond drop necklace by Piaget — and the decision to slick her hair back and keep the focus on her ensemble was totally correct.
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We saw a new side of Jessica Chastain fashion in 2021 — like this slinky Miu Miu confection she wore to the premiere of her film "The Eyes of Tammy Faye" at the 69th San Sebastian Film Festival. The long-sleeved black dress was anything but boring — check out the stone and crystal embellishments along the collar and hemline and that sky-high slit! But the truly surprising element is one you've got to see from another angle…
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Jessica Chastain's Miu Miu gown featured a totally open back also surrounded by stones. She styled this standout pick with a pair Stuart Weitzman satin platform pumps.
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Now that's a movie star! At the 2013 Academy Awards, Jessica Chastain made her fashion mark in this sparkling flesh-toned sparkling Armani gown. The red lip and the homage to Old Hollywood with the big waves in her hair solidified the look as one of our favorites ever from her.
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Jessica Chastain stuck to one of her favorite designers — Elie Saab — during the 2014 Cannes Film Festival. We loved the vibrant purple hue on the redheaded star and the way the one-shouldered gown draped and featured a wispy train. Adding to the glam? Her hair's voluptuous waves!
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Gorgeous! We don't normally see Jessica Chastain in a cropped look, so this Gucci getup was a delight to see on her at the Rome Film Festival in 2021. From the vibrant blue satin to the unexpected black crop top underneath to the slit and silhouette of that slinky skirt suit, this look at the photocall for "The Eyes of Tammy Faye" instantly became one of our favorites from the star. We particularly adored how she tied it all together with black pumps to complement the top.
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Blue might be Jessica Chastain's signature shade. She showed up at the Golden Camera Awards in Berlin, Germany, in 2019 in a strapless dress in regal royal blue that featured a sweetheart neckline, a thigh-high slit and train. When it came time to accessorize, she selected emerald and diamonds from Piaget and silver strappy sandals to complete her stellar red carpet moment.
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It was a bold blue-and-red Gucci gown for Jessica Chastain at the premiere of "The Eyes of Tammy Faye" during the Rome Film Festival in 2021. The sleeveless design featured a pale blue bodice — complete with a keyhole cut-out down the center — that gave way to a floor-length subtly patterned skirt with a delicate train detail. But the gown's best feature was actually its jeweled neckline, which we'll check out next…
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Check out the gorgeous gemstones along the neckline of Jessica Chastain's Gucci dress! The multicolored gems added even more pops of color to the already eye-catching frock, which also eliminated the need for any jewelry!
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Looking bold and bright in Armani Prive, Jessica Chastain stunned on the red carpet during the 2016 Cannes Film Festival. The strapless gown, which featured beautiful bustier detailing and a dramatic train, provided the perfect color pop and her Piaget diamond necklace added just the right amount of bling.
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The cobalt blue hue of the Elie Saab sleeveless peplum dress that Jessica Chastain wore to the Los Angeles premiere of "Zero Dark Thirty" in 2012 complemented her fiery locks perfectly.
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By now you may have noticed that Jessica Chastain has an affinity for Elie Saab. During the 68th Venice Film Festival in 2011, she wore a flesh-hued lace cap-sleeve gown by the designer to a screening of "Wilde Salomé." She topped off her look with a soft classic chignon and a berry lip.
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Jessica Chastain's 2021 Cannes Film Festival fashion game was on-point. She wowed at every appearance — particular at a Chopard dinner when she arrived in this emerald green Valentino creation. The spaghetti-strapped selection from the designer's 2022 Resort collection featured edgy cut-outs at the waist. She completed this look with bold Chopard jewels in equally memorable shades — earrings and a bracelet studded with purple amethysts.
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Flawless! Jessica Chastain glimmered in this black-and-green Altuzarra gown at the premiere of "The Huntsman: Winter's War" in 2016. The gown featured plenty of sparkle and geometric detailing — an unconventional combination. We loved the unexpected look on the star.
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You can't beat a cute minidress! Jessica Chastain proved this while arriving at the 69th San Sebastian International Film Festival in Spain in 2021 sporting this sweet Zuhair Murad outfit. The short-sleeved design featured gold embellishments along the collar and on the cool pocket details down the front and paired perfectly with those golden Christian Louboutins.
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Jessica Chastain opted for an ethereal look at the 2014 Governors Awards. The star donned an ivory layered Nina Ricci gown straight from the designer's runway and paired it with metallic Nicholas Kirkwood sandals.
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J'adore! Jessica Chastain arrived at the 40th American Film Festival in Deauville, France, in 2014 in this Oscar de la Renta minidress. The feminine floral fuchsia number featured flowers in metallic embroidery — and her styling was just as fab as the frock. She added an updo, a bold red lip and spiked Christian Louboutin pumps to the mix.
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Pantsuits sans undershirts are a risky pick, but Jessica Chastain pulled off this 2019 trend at the "X-Men Dark Phoenix" press conference in Mexico City that May. The star's fiery orange coordinates featured impossibly cool rolled-up sleeves and skinny trousers, and she added simple black pumps and a red lip to finish off the look.
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Dreamy in Dior! Jessica Chastain's elegant black Christian Dior ballgown with a sweetheart neckline stands out as one of her best ever Cannes Film Festival looks. She rocked the frock at the 2021 event while attending the "Annette" premiere, adding Chopard jewels around her neck for some sparkle.
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Jessica Chastain has continued to get more comfortable with flirty fashion throughout her career. Take this frilly Givenchy pick she wore in New York City in 2018, for example. The partially white, partially black printed wrap dress featured a bold white ruffled hem and a high-low hemline for a fun amount of drama, and she played into the dual-toned vibe with black-and-white sandals.
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Some things never change — like Jessica Chastain's penchant for Elie Saab. The beauty tapped the designer's Spring 2021 collection for a stunning look to wear during the 78th Venice International Film Festival in Italy in 2021. The pretty pale blue pick featured a sheer short-sleeved overlay atop a spaghetti strapped fitted midi-length design complete with a thigh-high slit. She added matching strappy sandals to finish off the look.
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Jessica Chastain looked fabulous in floral at the 2015 Empire Awards. The actress donned this black-and-white long-sleeved dress by Oscar de la Renta for the occasion and paired the glamorous gown with a simple topknot.
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Gold Givenchy! Jessica Chastain sparkled on the 2015 Met Gala red carpet. The star donned this shimmering halter-style gown, which molded to her body perfectly, and rocked her red hair in glam waves.
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We've always loved how Jessica Chastain never shies away from color. She arrived at the Ralph Lauren show during New York Fashion Week in September 2018 in this strapless yellow frock with a pleated tulle skirt. She then cemented this as an A+ look with a red lip and gold peep-toe pumps.
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For the 17th Annual Critics' Choice Movie Awards in 2012, Jessica Chastain opted for a simple pink halter dress by Balenciaga. She balanced out the volume of the bodice by pulling her hair back into a taut bun.
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A vision in black and gold! During the 84th Annual Academy Awards in 2012, Jessica Chastain dazzled on the red carpet in a strapless black Alexander McQueen gown with complex gold embellishments.
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Jessica Chastain glowed in green at a celebration marking the 40th anniversary of Charlie Chaplin's honorary Academy Award held at Los Angeles's Chateau Marmont hotel. We adored her her glamorous belted Elie Saab gown that accentuated her itty-bitty waist.
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Jessica Chastain proved that she isn't afraid of a little pattern sometimes. She donned this black-and-white Dolce & Gabbana dress during a photocall for "Madagascar 3" at the 65th Annual Cannes Film Festival in 2012. To offset the tricky-to-wear pattern featuring lace details, she added simple black Jimmy Choo sandals to her retro-inspired getup.
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This Calvin Klein Collection gown is simple in design, and the form-fitting nature of the garment flattered Jessica Chastain's petite frame. She topped off her look with minimal jewelry and a side-part wave during the 2012 Screen Actors Guild Awards.
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Jessica Chastain headed to an appearance on "The Late Show with Stephen Colbert" in New York City in 2021 in this killer blue David Koma jumpsuit. The beauty's sleeveless number featured buttons down the center, which worked perfectly with her silver strappy sandals.
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We're in love with the intricate construction of this buttery yellow Zac Posen gown that Jessica Chastain donned for a screening of "The Tree of Life" during the 64th Annual Cannes Film Festival in 2011. The bodice of Jessica's dress is absolutely divine.
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Straying from her usual feminine fashion choices, Jessica Chastain wore this black-and-white tweed-and-leather ensemble to the Proenza Schouler show during Spring 2013 Mercedes-Benz Fashion Week in New York City. She completed her look with pin-straight hair and simple black pumps.
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Pairing cherry red pumps with a neon green sleeveless sheath might be an unconventional choice, but it worked for Jessica Chastain when she was snapped at "The Late Show With David Letterman" in 2012.