Playboy Tiffany Taylor Despite what you see in these photos, Tiffany Taylor does not spend most of her time languishing amid beach dunes. Down 36, this week. Beverly Hills Video Playboy playmate tiffany taylor Herself. While competing in the Hawaiian Tropic national finals, she met a Playboy photographer. After high school, Taylor, whose beauty still charms hundreds of thousands of followers, attended the University of Maryland and studied criminal justice. Oh, and chocolate covered strawberries!