Jessica Chastain’s Red Lipstick Has Always Been Her Secret Beauty Weapon

She’s always been stunning.

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Jessica Chastain might be the reigning Best Actress winner, but her thoughtful roles and sophisticated aesthetic would make her just at home in Old Hollywood. Jessica Chastain’s beauty evolution is the progressive refinement of a woman who knows who she is. Ahead, a celebration of her best looks.

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Back in 2006, Jessica Chastain was working but largely unknown. Her signature fiery curls, though, would remain her beauty calling card for years to come. Marsaili McGrath/Getty Images Entertainment
Jessica Chastain’s always been a whiz with historic roles, but her patrician look and radiant red hair were taken to new heights thanks to a buzzy, Disney-themed photoshoot with the legendary Annie Leibovitz back in 2008.Handout/Getty Images Entertainment
While she’s gotten more experimental in the past half-decade, the bread and butter of Jessica Chastain’s beauty looks have always been cemented in the regal, sophisticated classics. For a Dior dinner in 2009, she opted for a softly sculpted updo.Toni Anne Barson Archive/WireImage/Getty Images
Jessica Chastain’s bangs would make a few surprise appearances over the years, but are rarely worn more casually than as part of this artfully undone ponytail at a 2011 Venice Film Festival screening. Pascal Le Segretain/Getty Images Entertainment
Consider 2013 the start of Jessica Chastain’s modern era. After a nomination and loss the previous year, she brought home a Golden Globe and stunned in these center-parted, pinned-back curls. Posing with her award in berry lipstick, she looks simply ecstatic. Steve Granitz/WireImage/Getty Images
Equally comfortable with long, flowing hair as she is a chic crop, Jessica Chastain’s side-parted lob was on more than a few vision boards back in 2015. It was arguably the Year of the Lob, and hers was among the best.Desiree Navarro/WireImage/Getty Images
Opting for a vintage, Gatsby-esque hair and makeup moment on the 2016 Cannes red carpet, Jessica Chastain’s wavy bob and dark smoky eye are a refreshing switch-up. At this point, she’s beginning to play with her fashion choices, too.Samir Hussein/WireImage/Getty Images
The bangs are back! In early 2019, Jessica Chastain kept her bob neat and trim but added a set of thick, straight-across bangs — and made sure her hair was the shiniest it’d ever been. Victor Chavez/Getty Images Entertainment
One of Jessica Chastain’s best makeup tricks is keeping her entire look very fair and minimal, and then adding a dramatic lipstick to bring it all to life. Redheads are always stunning in a matching red lip, but this oxblood shade from 2021 is so luxe. Dominique Charriau/WireImage/Getty Images
Holding the 2022 Best Actress Oscar, Jessica Chastain is just electrifying. Her long, soft curls were in a pony for the ceremony but fluffed up and brushed for the all-important afterparty. Her soft matte lipstick, a muted mauve, lets her gown (and her golden statue!) have all the glory. PATRICK T. FALLON/AFP/Getty Images

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