Tracy Lord From The Philadelphia Story What to wear: A sensible black blouse tucked into really high-waisted trousers. Fold the front of your hair back to get that '40s look. How to act: Like a wealthy socialite who isn't afraid to wear trousers. Bonus: if there was ever a time to try your hand at the transatlantic accent, it's while you're dressed like Katharine Hepburn. Image Source: Getty