Guys how do you approach the?

Guys how do you approach the unapproachable? You know what I mean, those "elite" girls in your neighborhood, who have the biggest and best parties, who always have only the hottest girls and only gq girly men with fancy new cars on their guest list. There's one girl that is really nice and works near to where I work, and even at work, she's looks like she would be way out of my league. How does a guy approach a girl like that for a date without looking like a fool for asking?