Ostrander is a 2007 graduate of St. Augustine High School and has a degree in photography from Daytona Beach State College. She is a self-proclaimed tomboy who has surfed competitively, camped, and traveled around the world. She is also a sailing enthusiast and moved to San Francisco to learn how. Afterwards, she began exploring the Pacific Ocean on a 41-foot yacht named Journey. Ostrander's first long-distance voyage was a trip from San Francisco to Bora Bora, a distance of over 7,000 nautical miles, with a stop in Hawaii. It was while docked in Hawaii that she perused a collection of Playboy magazines and came up with the idea of submitting her photos.