She attended Fox Chapel High School in suburban Fox Chapel, Pennsylvania, and went on to study English Literature at the University of Pittsburgh where she was a member of the Delta Delta Delta (Tri-Delt) sorority.
She is the wife of radio personality Howard Stern. She has two brothers. Ostrosky worked as a model while in high school.
She moved from Pittsburgh to New York City to pursue her modeling career soon after and worked for several of the fashion houses in New York City in the early 2000s.
Soon after her arrival in New York City, talent scouts began to take notice of her, and offered her small parts in movies and television ad campaigns. She received her first noticeable role as one of the daughters of Ben Stiller"s supposed birth parents in the 1996 film, Flirting with Disaster.
Stern played a more prominent role four years later, in the film Whipped, with Amanda Peet. Ostrosky has also appeared on television, appearing in the final season of G4 show Filter, and the Spike television series Casino Cinema.
She has appeared in her own line of calendars, as well as on the covers of several magazines.
She has been on the cover of FHM three times. Votes from the readers of Foreign Him Magazine ("FHM") placed Stern among FHM"s 100 Sexiest Women of the Year in 2002, 2003, 2004, and 2007( #76). AskMen.com placed Stern 96th in its list of the Most Desirable Women for 2007.
She is signed to Click Models, in Boston and New York City.
Proceeds from the book went to support Bianca’s Furry Friends, a 15,000-square-foot, cage-free animal shelter at the North Shore Animal League, named after the couple"s deceased bulldog. In 2015, Ostrosky-Stern wrote a sequel Yoda Gets a Buddy.