Stewart's romantic life has been the subject of many press and television tabloids. Most notably she had a relationship with singer Cisco Adler. Stewart got a tattoo reading "Daddy's Little Girl Loves Cisco", which, after their breakup, she changed to

Stewart's romantic life has been the subject of many press and television tabloids. Most notably she had a relationship with singer Cisco Adler. Stewart got a tattoo reading "Daddy's Little Girl Loves Cisco", which, after their breakup, she changed to "Daddy's Little Girl Loves Disco". After a lack of interest in disco, she added the letters "unts" after the word Disco to make the tattoo say "Daddy's Little Girl Loves Discounts".

As well as coming from a rich and well known family, Stewart is well-known in US tabloids for her many celebrity-friendships, including Paris and Nicky Hilton, Courtney Love, Anna Nicole Smith, Kelly Osbourne, Lindsay Lohan, Bijou Phillips, Jack Osbourne, Bai Ling, Kim Kardashian and Caroline D'Amore.

Paris Hilton and Stewart have topped People for the Ethical Treatment of Animals (PETA) year-end Worst Dressed poll in early 2005. The two were named among the five worst fashion offenders due to their "tacky affinity for fur".