Guess Who? A Look Back at the Ten Most Famous Guess Girls

We were all completely blown away by the images released earlier today of Claudia Schiffer's new campaign for Guess, twenty-three years after the German supermodel originally posed for the brand. Two decades later, the lady still looks as Guess-girl flawless as she did back in 1989, before she attained her supermodel status. It got us to thinking: In the thirty years of Guess's existence, which other big-names got their industry start modeling for the brand? We did a little digging, and as it turns out, there have been quite a few more than you might Guess (ha!). It seems like Victoria's Secret (you know, that other brand known for its seriously sexy campaign starlets) has a habit of plucking its Angels from the pool of genetically blessed Guess girls. And then, there have also been a few Guess missteps (coughParis Hilton). Click through for some of the lucky girls who've followed in Claudia's well-pedicured footsteps: Scoring both a Guess contract and the (generally) good career fortune that seems to follow, with a few exceptions.
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Nora Crotty
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We were all completely blown away by the images released earlier today of Claudia Schiffer's new campaign for Guess, twenty-three years after the German supermodel originally posed for the brand. Two decades later, the lady still looks as Guess-girl flawless as she did back in 1989, before she attained her supermodel status. It got us to thinking: In the thirty years of Guess's existence, which other big-names got their industry start modeling for the brand? We did a little digging, and as it turns out, there have been quite a few more than you might Guess (ha!). It seems like Victoria's Secret (you know, that other brand known for its seriously sexy campaign starlets) has a habit of plucking its Angels from the pool of genetically blessed Guess girls. And then, there have also been a few Guess missteps (coughParis Hilton). Click through for some of the lucky girls who've followed in Claudia's well-pedicured footsteps: Scoring both a Guess contract and the (generally) good career fortune that seems to follow, with a few exceptions.
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We were all completely blown away by the images released earlier today of Claudia Schiffer's new campaign for Guess, twenty-three years after the German supermodel originally posed for the brand. Two decades later, the lady still looks as Guess-girl flawless as she did back in 1989, before she attained her supermodel status.

It got us to thinking: In the thirty years of Guess's existence, which other big-names got their industry start modeling for the brand? We did a little digging, and as it turns out, there have been quite a few more than you might Guess (ha!). It seems like Victoria's Secret (you know, that other brand known for its seriously sexy campaign starlets) has a habit of plucking its Angels from the pool of genetically blessed Guess girls. And then, there have also been a few Guess missteps (coughParis Hilton). Click through for some of the lucky girls who've followed in Claudia's well-pedicured footsteps: Scoring both a Guess contract and the (generally) good career fortune that seems to follow, with a few exceptions.

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Claudia Schiffer

Claudia first modeled for Guess back in 1989 at age nineteen, and definitely set a high standard for other Guess girls who followed. With her bouncy blonde hair, enviably extensive lashes, and to-die-for sex faces, the German model epitomized the glam cool-girl aesthetic for which the company came to be known. Now twenty-three years later, we're actually having trouble identifying which of her campaigns are old or new. Hot damn.

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Anna Nicole Smith

In 1993, the controversial late tabloid queen was chosen to succeed Claudia Schiffer as the next Guess girl. Her gorgeous and sultry Guess ads paint a much different picture than the constant lawsuits, drug use, and weight fluctuation that plagued Anna Nicole's tumultuous personal life. With her ample curves and larger than life personality, Anna Nicole Smith is still considered as the ultimate Guess girl.

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Laetitia Casta

Fine French femme Laetitia Casta modeled for Guess in 1993, a role which still stands as one of her most well known-- perhaps due in part to her miraculous ability to pose atop ocean water. She went on to pose for Victoria's Secret, L'Oreal, Dior, Chanel, and cover countless glossies. Laetitia was also awarded one of the highest honors a (gorgeous) woman can receive in France: In 1999, she was chosen to be the new face of 'Marianne,' the allegorical symbol of the French Republic-- Previous Mariannes include Brigitte Bardot and Catherine Deneuve. That's some seriously sexy company.

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Drew Barrymore

Drew Barrymore was already a household name when she got kinky on this carousel for Guess in 1993. While she's obviously most well known for her roles as an actress and film producer, Drew has actually been the spokesmodel for several popular beauty and high fashion brands including Miu Miu, Missoni, Gucci, Lancome, and Covergirl-- all following her stint as a Guess girl.

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Josie Maran

Josie Maran had already landed a cover of Glamour when she became a Guess girl in 1998, but her career only catapulted in the years to follow her Guess campaign when she was signed to a multi-year contract with Maybelline. Since then, she has gone on to launch her own eponymous line of natural cosmetics and has her own character in the video game Need for Speed: Most Wanted. Josie's early Kate Moss-esque Guess campaign is definitely one of our favs. Fun fact: She apparently was once in a band with Nicole Richie.

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Alessandra Ambrosio

Based on this low-key Guess campaign from 2000, who could've guessed that Alessandra Ambrosio would go on to be one of the biggest Victoria's Secret Angels of all time? Looking more appropriate for a co-ed summer camp dance than a fashion shoot, the Brazilian babe also posed for Guess with fellow VS model Ana Beatriz Barros.

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Adriana Lima

Adriana Lima might have single-handedly increased trends in lip enhancements, self-tanning, and hair extensions when she posed for this Lolita-looking Guess campaign in 2000. The Brazillian bombshell has gone on to become not just a Victoria's Secret Angel, but also one of fashion's most recognizable (and bankable) faces since then. She's currently the star of Donna Karan's Spring 2012 campaign.

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Jessica Hart In 2007, Aussie model and street style star Jessica Hart was welcomed as a Guess girl. Her winged liner, bronze skin, and toned tummy put her right up in the ranks with the other classic Guess stunners. It's hard to believe our fair Jessica was eventually succeeded by our next 'model'...

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Paris Hilton

Oh Paris. The heiress's trashy 2009 Guess campaign was definitely a throwback-- to a time when people actually cared about Paris Hilton (which was around 2006). Its study-in-excess theme is about as far removed from the minimalist Josie Maran campaign as it gets. Will someone please get that chihuahua some tiny sunglasses? And disinfectant spray?

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Kate Upton

Before she covered this year's Sports Illustrated Swimsuit Issue, but after she did the Dougie on YouTube (so, 2010-11), Kate Upton spent a hot minute as a Guess girl. The teen model channelled fellow bombshell blondes Claudia and Anna Nicole in her campaign, also starring in a fairly soft-core B&W video clip for the brand's lingerie line.