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All About Elle Strauss, Shopbop's NYC Fashion Director
High-waisted jeans paired with a flannel shirt has long been a classic American look.
Brook Shields sparked controversy with this ad when the then-15-year-old said that "nothing" came between her and her Calvins.
An Ode to Carrie Bradshaw's Epic Shoe Game
No ad better captures denim trends of the late 1980s and early 1990s than this Versace spread.
Don't be fooled by their seemingly sultry connection. Calvin Klein revealed in Interview magazine that Kate Moss and Mark Whalberg were not enthused with one another during this shoot.
This early '90s campaign turned Anna Nicole Smith into a household name. Smith replaced supermodel Claudia Schiffer as the face of Guess.
Resembling the iconic World War II First Kiss photograph for Life Magazine, Diesel's early '90s ad featuring two gay sailors kissing was shot by artist David Lachapelle and became one of the most famous ads ever.
Despite our best efforts, who can forget this stage in denim history?
Heidi Klum became a spokesperson for the iconic denim company with this racy ad.
Gap denim + West Side Story—we're still hooked.
Daria Werbowy showed off how to effortless pair denim-on-denim in this laid back H&M ad.