Cindy Crawford | Bentley Continental GT | Approximately $202,500

One of the most popular supermodels of the ‘80s and the ‘90s, Cindy Crawford, had a very prolific career, appearing on the cover of many magazines and in various campaigns. Realizing the value of her brand, she then started making investments in her own business. Crawford also expanded her career to include acting. Some would probably remember her from films like Catwalk and The Simian Line.

While a very busy supermodel, Crawford has also shifted her focus to her family. She is a very active participant in charity events, as well. Whenever she goes around to various engagements she is a guest of, she uses her Bentley Continental GT. It is one of the more expensive ones in her collection and the right vehicle when rubbing elbows with people of stature. She probably uses a more discreet car when going out with her kids to avoid prying eyes.