Summer Chic

Another outfit try on, can you tell I'm trying to suck in my stomach? I find that I am much more interested in the wild, bright prints ah-la Lilly Pulitzer, than the staid tailored dresses I've been finding. How can I express myself and take this persona on at the same time? How did these women express themselves through their clothes? Did they try?
The other problem is shoes. For Pete's sake, I never wear high heels and some of these dresses absolutely require them. I know that women wore little ballet-type flats too, at least I think so, but I'm thinking these shoes were only worn around the house or with pedal-pusher pants. I know all this will become more clear as I delve deeper into my research, but I'm swimming around with a lot of questions right now.