BEST GUESS

Guess Models Through the Years, from Anna Nicole Smith to Sydney Sweeney

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The American label Guess has a history of turning girls into supermodels and celebrities into fashion icons. Take Anna Nicole Smith, for example, a then little-known model who replaced Claudia Schiffer as the face of the brand back in 1992 and instantly catapulted to a higher level of stardom. Then, there are the ones who start young, a la Gigi Hadid, whose modeling career began all the way back in 1997 when she began modeling for Baby Guess when she was just two years old; flash forward to 2017, and the blonde beauty is one of the most in-demand faces in the world. Meanwhile, celebrities like Camila Cabello, Joe Jonas, and Jennifer Lopez have all done promotional stints for the brand.

The latest up-and-comer to get in the good graces of Guess? The White Lotus and Euphoria star Sydney Sweeney. In a mark of the brand’s heritage, her campaign directly references Anna Nicole Smith. Take a look at Sweeney’s new campaign and all the famous Guess “whos” over the years.

Sydney Sweeney
courtesy of Guess

Sydney Sweeney’s Guess Originals campaign doesn’t channel Anna Nicole Smith by mistake. It’s for the brand’s new Anna Nicole capsule collection. Photographer Kenneth Cappello used unpublished photos from a 1992 shot of Smith by Daniela Federici as inspiration.

Sydney Sweeney
courtesy of Guess

The GUESS Originals x Anna Nicole Smith Collection, designed in conjunction with Cali Thornhill Dewitt, take inspiration from another 1992 photoshoot of Smith in Miami by Wayne Maser. Vintage photos and the color teal, reflecting the waters of Miami, are used throughout.

Sydney Sweeney
courtesy of Guess

The collection mixes current trend with ‘90s inspiration, but Sweeney herself looks timless.

Jennifer Lopez
Image Courtesy Guess

In 2018, Jennifer Lopez took her turn as a Guess girl. She returned in 2020, and helped edit a capsule collection.

Camila Cabello
courtesy of Guess

Upon her transition to solo star, Camila Cabello also did time as a Guess girl.

Ireland Baldwin
Getty

Ireland Baldwin stared as Guess’s face for their Fall ’17 on-campus campaign shot by photographer Tatiana Gerusova.

Hailey Bieber
courtesy of Guess

Back when she was known as “Hailey Baldwin,” an up-and-coming Hailey Bieber did several campaigns for Guess.

Hailey Bieber
courtesy of Guess

Bieber returned for several seasons.

Gigi Hadid
courtesy of Guess

Gigi Hadid famously starred in a Guess campaign a two-year-old, and returned to model for the brand for several seasons as a teenager which lead directly to her current status as “supermodel.”

Joe Jonas
courtesy of Guess

While the brand is best known for its female faces, Joe Jonas’s 2017 underwear campaign remains seared in some people’s brains.

Naomi Campbell
courtesy of Guess

Naomi Campbell modeled for Guess often throughout the ‘90s.

Naomi Campbell
courtesy of Guess

She returned to the brand in 2016 to pose alongside A$AP Rocky.

Alessandra Ambrosio
courtesy of Guess

Alessandra Ambrosio also did several Guess campaigns.

Alessandra Ambrosio
courtesy of Guess.

She wasn’t afraid to let out her wildside.

Kate Upton
courtesy of Guess

Kate Upton of course fits the prefect Guess girl image.

Laetitia Casta
courtesy of Guess

Laetitia Casta did her time as well.

Adriana Lima
courtesy of Guess

Adriana Lima appeared in a few Guess campaigns.

Drew Barrymore
courtesy of Guess

During her wild child days in the ‘90s, Drew Barrymore also did a campaign for Guess.

Anna Nicole Smith
courtesy of Guess

Of course, its Anna Nicole Smith who remains perhaps the most legendary Guess girl.

Anna Nicole Smith
courtesy of Guess

Her Guess campaigns helped catapult her into the mainstream.

Claudia Schiffer
courtesy of Guess.

Though, it was technically Claudia Schiffer who preceded her in the role of Guess blonde.

Claudia Schiffer
courtesy of Guess

Schiffer’s work for Guess began before she was a full-fledged supermodel. By the end of the ‘90s, she’s be a Chanel regular.