I want to dress more femininely but don't know how to make the gradual change. Advice please?

I really like the look of ballet flats but not skimmers. Would it look bad if I had a pastel coloured fitted t-shirt with some embroidery (already have a few) and light coloured jean capris (have) would it look okay with flats? If so, what kind should I look for. I also want the change from plain to more feminine gradual, I thought flats would be a nice start....