That's the advantage of wearing the same old thing — here, host Ryan Seacrest looks like he's the one committing the fashion faux pas. The fourth "Idol" season's a tumultuous one, with two contestants quitting, but 2005 is also the year Carrie Underwood wins. In May, Simon faced Oprah and survives her questions and video clips, like the one with Ryan talking about how Simon's "T-shirts are too small, they're too tight…The man-boobs — we really have to reduce the size." But Simon does admit to one fear: "I'm turning into Paula…For one moment, I used the word 'proud.'" He doesn't have to worry long: Before the year's out, he signs a five-year contract with Fox, making him the richest person on American TV.
Check out Simon Cowell's "American Idol" fashions.