16. 1965 Autobianchi Eden Roc

The Lady In Question: Audrey Hepburn
The Circumstance: Tooling around in the 1966 film How To Steal A Million
This Moment Strikes Us: as telling. Even if Ms. Hepburn wasn't a style icon for the ages, you'd still know she's hot just by looking at this photo. You have to be beautiful to carry off a hat like that.