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Drew Barrymore, 1993

Here, the best Guess ad campaigns through the years, starring Drew Barrymore, Anna Nicole Smith, and more.

Claudia Schiffer, 1990

30 Sexy Years – Guess’ anniversary campaign taps supermodel Claudia Schiffer for a series of sexy and flirty black and white images shot by Ellen von Unwerth.

Guess Girls Through the Years - Guess Jeans Models - Elle

We revisit the most iconic Guess Girls through the years, from Anna Nicole Smith and Claudia Schiffer to Gigi Hadid.