1. In 2003, the Gap announced they had gotten Madonna, the ultimate a fashion icon, as the face of their fall campaign, called “A New Groove, A New Jean.”
Madonna wore Gap low rise cropped cords and a ribbed white tank top. She completed her look with $5 million in diamond jewelry from Neil Lane.
2. While Madonna was no stranger to fashion ad campaigns — she had famously been the face of Versace in 1995 — this was her first foray into a lower-end brand.
She has since then collaborated with lower-end fashion companies like H&M and Macy’s.