Today, Lindsay Lohan turns 27. The star has come a long way since she first appeared as adorable, freckle-faced twins Hallie and Annie in the superb film The Parent Trap at age 11. Since then she’s dated Aaron Carter, starred in Mean Girls (nine years ago!), dated Sam Ronson, visited rehab numerous times, founded a line of leggings, and played Elizabeth Taylor in the Lifetime classic Liz & Dick. Throughout all this, Lohan has made notable fashion decisions, from sheer dresses and breast-baring necklines to more conservative attire (and now infamous nail art) for probation hearings. In honor of her birthday, check out Lilo’s most notable sartorial moments in our look book below.