Jean Shrimpton photographed by Richard Avedon. This photograph is effective in terms of shadowing, the angle that it is taken at shadows her main features therefore dominating any flaws. This image really brings out her eyelashes.
This combines elements of all three things he loves the most: timeless, sexy, and dark. The look over her shoulder with her hair hiding her face gives her level of mystery and sexiness. The dress, and the hair are very timeless.