 Jennings has won awards for her feature writing, her car reviews, and her monthly "Automobile Magazine" column “Vile Gossip,” including the 2006 Ken Purdy Award for Excellence in Automotive Journalism.In particular, she works to give women a voice in the male-dominated automotive space.She has stated that she started the website JeanKnowsCars.com to provide a perspective on buying, owning and enjoying cars for people who don’t read specialized auto-enthusiast publications, explaining, “I know the secret car-guy handshake, so you don’t need to.”

Jennings was the subject of a Susan Orlean profile in "The New Yorker", appeared on "The Tonight Show with Jay Leno," and was "Good Morning America’s" automotive correspondent from 1994 to 2000.