Cher

Cher has been known for many things – like a successful music career and impressive, award-worthy acting chops – but unfortunately good fashion sense isn't her strong suit. In 1998, she showed up to the Oscars with her son Elijah Blue wearing a semi-transparent, nude-colored web of a dress, complete with a matching headpiece. Believe it or not, this is just one of her many theatrical ensembles, and not in a good way! Photo: ©Vince Bucci/KPA-ZUMA/KEYSTONE Press