"If I were a woman, I think I'd wear high heels." That's Mayor Michael Bloomberg, to the New Yorker's Rebecca Mead. The full quote: "I like women and I think that they look stunning in high heels — not that they look bad without high heels. I wouldn't criticize anybody." 

But this is not the first time Michael Bloomberg's thoughts have publicly wandered to what he'd wear had he been born a member of the fairer sex. When he was photoshopped wearing a nanny's outfit in an attack ad, he replied with "Would I wear a dress like that? No! It was one of the more unflattering dresses." And on a talk radio show, discussing his opposition to a policy that would allow cab drivers to deny admission to customers they thought might be prostitutes, he declared that if he were "a young lady," attired "in a sporty way," he wouldn't want to be mistaken for a lady of the night. He'd never wear such "sporty" gear to work, "but at night, sometimes, sure." Well, mayor, there are a few more nights left in your administration—and it's not as if New York mayors haven't explored such sartorial choices before.