Roxette, "Dressed for Success"

Let's see, in 1988, you'd be coming off a massive hangover after celebrating Australia's bicentennial. Perestroika would have just begun; so, you'd want to wear something sensibly structured. Hustler had just beaten Jerry Falwell in the Supreme Court, which means slightly trampy would be okay. The Cubs would've played their first night game at Wrigley Field, and Lloyd Bentsen would've informed Dan Quayle that he was, in fact, not Jack Kennedy.

According to our ANABlog Fashion Calculator (Patent-Pending), you'd want to go BIG. We're talking big glasses, big hair, big shoulder pads. As long as you pretty much looked like you'd just stepped off the set of Working Girl, you could consider yourself dressed for success: