Lindsay Lohan has been acting since her commercial and soap opera beginnings in the early '90s, and, of course, she broke big at the age of 12 when The Parent Trap came out in 1998. That means she has a whole fashion history filled with red carpet premieres, and each look represents a new phase in her career. So, while promoting the Freaky Friday sequel Freakier Friday, Jimmy Fallon busted out a picture of Lohan from the 2003 movie's premiere, and she was actually her own worst critic.
Being in the movie industry since childhood, Lindsay Lohan’s fashion journey has evolved dramatically from playful red carpet looks to a more adult, sophisticated style. When she appeared on The Tonight Show to promote her 2025 movie release, Freakier Friday, Jimmy Fallon busted out a photo of Lohan from when she attended the OG Freaky Friday premiere. Surprisingly, she was quite critical of herself, saying:
