These days, Gwyneth Paltrow is most well-known as the founder of newsletter-turned-lifestyle company Goop, but she’s also a red carpet veteran. Photographed as a teen alongside her parents, producer-director Bruce Paltrow and actress Blythe Danner, Paltrow began establishing her on-screen career in the early ‘90s. As her star power rose to include leading roles in films like Emma and Shakespeare in Love (the latter for which she won the Best Actress Oscar in 1999), so, too, did her style status.

Embodying the trends of the ‘90s with a mix of more casual, oversized looks and simple slip dresses at the start of her career, Paltrow’s style evolved to include brightly colored custom gowns and tailored menswear, before embracing a more classic look with the launch of her clothing line, G. Label by Goop in 2016. Working with longtime stylist Elizabeth Saltzman has also helped to refine the actress’ sartorial tastes during their 15-plus years of collaboration, but Paltrow has never strayed too far from her initial preferences (or her favored designers like Calvin Klein, Stella McCartney and Tom Ford). “I always say I’m kind of preppy with a twist,” Paltrow told Vogue of her style tendencies. “I’ve always loved great tailoring and things that Anjelica Huston would have worn, or Diane Keaton,” she added of where she gets her inspiration.

Ahead, we’re taking a look back at some of Paltrow’s most memorable moments in fashion—from her first Met Gala to wearing a custom design from her very own clothing line.

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Paltrow’s earliest red carpet days were always more casual, even when attending a premiere for her own film, as was the case with this oversized leather jacket and combat boot pairing for the Hollywood premiere of Flesh & Bone.

“This was my era of Calvin Klein,” Paltrow told Vogue while reflecting on her very first Met Gala in the ‘90s. Before the days of the first Monday in May, Paltrow explained that the annual event benefiting the Metropolitan Museum of Art’s Costume Institute was a quieter affair, which is how the actress landed on a white tank dress from Calvin Klein. “I was so thrilled because he always wanted to dress me and lend me beautiful things,” she said of working with the designer. For the Met Gala, Paltrow styled her slip dress with all-black accessories, and a sleek hair and brown lip liner combo that served as the decade’s defining beauty look.

At the Los Angeles premiere of From Dusk Till Dawn, Paltrow broke up an all-black ensemble with a leopard print coat (and Converse sneakers).

Paltrow made her go-to slip dress a little more glamorous by opting for an embellished number to attend the Academy Awards with then-boyfriend Brad Pitt.

1996 marked a turning point in Paltrow’s career, as she began landing more starring roles, such as the titular character in Emma, an adaptation of Jane Austen’s novel of the same name. Celebrating the film’s New York City premiere alongside her family, Paltrow stepped up her red carpet style with a classic black slip dress. To show off the crisscrossing strap details at the back, the actress wore her hair in a tousled updo with face-framing pieces and bolder makeup that included a smoky eye and brick-red lipstick.

The actress exhibited her love for a menswear look when she walked the red carpet at the MTV Video Music Awards in a red velvet suit from Gucci’s then-creative director Tom Ford. “He completely revolutionized the brand,” Paltrow told Vogue of Ford’s work with Gucci, noting that the suit remains one of her favorite red carpet moments decades later. “Everybody was clamoring to get anything they could from the collection, and I was very lucky to borrow this beautiful red velvet tuxedo from........

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