The beautiful Audrey Hepburn (I know - a little obvious)

Totally stunning (look at that beautiful face), amazing figure (if not a little too thin, but she never looked gaunt), beautiful style! If it wasn't full circle skirts, or pedal pushes and a beatnik style, then it was sharp tailoring and fash-forward frocks.
Princess Margaret (of England)
A ravishing beauty which such poise and elegance with a hefty dose of 'IT GIRL' about her as well. She was friends with the movers and shakers of the time and not being the Heir apparent, was able to let her hair down (although it was usually up in a massive Beehive!)

Sophia Loren
What's not to love about this gorgeous women - she was rocking a killer curvy figure when it seemed most women where more cigerello in figure

Let's get in our time machine and hit up some more modern ladies...
Victoria Beckham
I heart her - I know she's not a popular choice and she has worn some bloody awful stuff, but she has been getting it right more and more recently with a more classy style and feminine shapes (also still too thin).

Carry Mulligan
I think she keeps it stylish whilst still being a bit out there and kooky-cute
