Gwyneth Paltrow
Clearly the upper management of the 2002 Oscars lifted their “no shirt, no bra, no service” rule especially for actress Gwyneth Paltrow. Tapping into her goth side to pull off this Alexander McQueen number, Paltrow must have failed to check out how her chest would photograph under the near-constant flash of the paparazzi. Paired with the shapeless velvet skirt, this look is undeniably a fashion fail.