But new photos of the 26-year-old actress shopping in Venice, Calif., have us wondering if she looked in the mirror before she left the house. In the photos, Lohan is wearing a white halter top with no bra -- and for a busty star like LiLo, that meant she showed off a lot of side boob and it wasn't particularly flattering.
Let's just say she didn't pull it off as well as side-boob flashing expert Miley Cyrus.
Lohan's letting-it-all-hang-out look marks the second time this week that we've been confused by her styling choices. On Aug. 13, the "Mean Girls" star stepped out making multiple makeup faux pas including: bubblegum-pink lipstick that extended far past her natural lip line, over-the-top dramatic cat eyeliner and overly contoured cheeks.