On September 2, Jessica Chastain made a striking appearance on The Tonight Show with Jimmy Fallon, wearing signature millennial fashion trends, including a side part hairstyle and gladiator sandals. The actress, who announced she is returning to school to pursue a master’s degree at Harvard, demonstrated her style alignment with contemporary youth culture despite being born before the millennial generation.
During her appearance, Chastain sported flowing red hair parted to the side, paired with heeled gladiator sandals by Rene Caovilla, a Gucci mini dress, and Gucci sunglasses at times. This outfit reflected current millennial-coded fashion choices that contrast her personal stance on other trends from the early 2000s.
Chastain Rejects Low-Rise Fashion Resurgence
Although her look embraced certain modern trends, Jessica Chastain made clear she will not support the comeback of low-rise jeans, a style popular among millennials in the 2000s. Speaking to Elle Spain, she expressed strong disapproval of the trend creeping back into fashion.
“I know this is coming back, but the low-rise jeans, I hate,”
she stated.
“And I hate when you see someone’s underwear. I think it’s so tacky, like, when it’s like a G-string. I think it’s horrific.”
—Jessica Chastain
She further criticized the style of shorts that reveal too much, adding her preference is for more coverage in clothing. “I’m into full-coverage clothing,” she emphasized, highlighting how some trends do not fit her personal taste even as she embraces others.
Her Approach to Fashion: Personal Expression Over Trends
In the same interview, Chastain shared that she does not closely follow fashion fads but rather wears what she likes. She explained that if she secretly desired a trend to return, she would simply incorporate it into her wardrobe without concern for public opinion.
“If there was a trend that I’d secretly wish would come back, I would just wear it,”
she said.
“I don’t feel like, ‘Oh, I’m not allowed to wear that because people say.’ So I don’t really have one of those. I kind of just wear what I like.”
—Jessica Chastain
Chastain’s Academic Pursuits and Intellectual Curiosity
Aside from fashion, Chastain opened up about her decision to pursue a master’s degree in public administration at Harvard University. She described this educational venture as motivated by a desire to expand her knowledge and called the degree “the sexiest degree ever.”
Having previously graduated from The Juilliard School, where she studied acting, she identified herself as “a secret nerd” and expressed enthusiasm for academic subjects such as scatter graphs and bell curves.
“I get the hots for, like, scatter graphs and, like, bell curves,”
Chastain revealed.
“My goal is to take over the world.”
—Jessica Chastain
Breaking Family Patterns Through Education and Theater
Reflecting on her personal background, Jessica Chastain shared how she was the first in her family to avoid teenage pregnancy, finish high school, and attend college. She credited The Juilliard School with changing her life and demonstrating to her family that different futures were possible.
“I was the first in my family to not get pregnant as a teenager, the first to finish high school, and the first to attend college,”
she said.
“And attending The Juilliard School didn’t just change my life. It showed my family that a different path was possible.”
—Jessica Chastain
Chastain described her path as one of determination, with theater serving as a vital outlet. Speaking at a December 2024 event, she told the gathered audience that theater was her lifeline, allowing her to be seen, use her voice, and break free from generational expectations.
“It was a way to feel seen, to use my voice, and to break free from the expectations that had bound my family for generations.”
—Jessica Chastain
Significance of Chastain’s Style and Personal Journey
Jessica Chastain’s public embrace of millennial fashion trends, combined with her rejection of others, highlights an actress navigating contemporary style on her own terms. Her choice to pursue further education amid a successful acting career demonstrates her commitment to personal growth, intellectual curiosity, and breaking longstanding family patterns.
As she continues to balance Hollywood and Harvard, Chastain’s evolving public image and fashion choices will likely influence admirers who value authenticity and empowerment, reinforcing her role as both a style icon and an advocate for lifelong learning.
