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Former ‘Guess Girl’ Drew Barrymore Inspires the Brand’s Latest Collection

Once a Guess girl, always a Guess girl. The iconic brand is celebrating this sentiment with a capsule collection centering on actor Drew Barrymore, whose career pivoted in the early ’90s after the Los Angeles-based label featured her in a memorable campaign shot by photographer Wayne Maser.

“There has been such an overwhelming number of people who mention her ’93 campaign when they discuss Guess’ most memorable work,” said Nicolai Marciano, Guess director of brand partnerships. “In comparison to other legacy models we have worked with in the past, the time period of Drew’s career felt like the perfect unexpected moment of nostalgia to introduce to a new generation of Guess fans.”

Though her Guess campaign is nearly 30 years old, the era Barrymore represents continues to be part of the current cultural zeitgeist. The actor has been the subject of several popular songs in recent years, including Bryce Vine’s “Drew Barrymore” and Sza’s song by the same name. She also recently launched her own talk show, “Drew Barrymore Show,” to spread positive news stories from her perspective, and has her own beauty line.

The collection was developed in collaboration with streetwear brand Pleasures, an L.A.-based label known for its punk and grunge influences. The line consists of 36 pieces for men and women printed with Pleasures branding and ’90s Guess campaign imagery featuring Barrymore.

Anchored by ’9os-style denim decorated with bold prints—including a pair of white jeans featuring Barrymore’s left eye on the back leg—the collection celebrates never-before-seen images from the campaign. Other standout denim pieces include a black high-rise kick flare jean with gray polka dots and light-wash jeans and a matching denim jacket laser printed with Barrymore’s headshot. Sweatpants, hoodies, T-shirts, tank tops and accessories such as hats, totes, socks and sunglasses round out the collection.

Guess often celebrates its star-studded brand ambassadors, and in 2018 released a collection honoring the late model and former Guess girl Anna Nicole Smith.

The Guess Originals x Pleasures Drew Barrymore collection marks the third collaboration between the two brands. It is immediately available online and at select Guess stores, and retails for $22 to $128 for men’s apparel and $34 to $108 for women’s.