Most Beaufitul 1993: The 27-year-old supermodel was on a roll that year: She was the face of Revlon, had a hosting gig on MTV's House of Style and was married to future Sexiest Man Alive Richard Gere (he earned that distinction in 1999). Now: In the 20 years following her Most Beautiful cover, Crawford got divorced, remarried and launched successful home furnishing, fashion and skincare lines. She also developed a good attitude about getting older. "I take care of myself, but I don't want to be obsessive," the 47-year-old mom of two told Allure. "I'm all for fighting the good fight, but I don't care how much you work out or how much cream you put on – things change."