As always, Tim Gunn is hesitant to call anything a ‘Fashion Don’t,’ because he likes to view the clothing in the context of the wearer’s personality. “The clothes we wear send a message about how we’re perceived.”
That said, sometimes looks can send confusing messages, so rather than trash celebrities, he and Ali discussed “the most perplexing” celebrity looks of all time.
High on Tim’s list is Helena Bonham Carter, whose red carpet style he finds, “a little off-putting.” He may also have whispered the phrase “hot mess.”
Also on the list is Paris Hilton. “I think we’re the butt of all her jokes,” says Tim. “She dresses to be a ridiculous cartoon character.”
WATCH: More Fashion Fails
Number one on Tim’s list, he says, has offended a lot of people in the past. To see his controversial pick, and a few celebs who always get it right, watch this episode of Daily Shot.