Get yourself some of those cute slip on tennis shoe style things for working out that are flat and slip on but have some style. People wear them for yoga and such. Try http://www.lucy.com - they have the best workout gear, I just love them. They go with casual clothes. And when you are ready for flats - maybe try http://www.aerosoles.com - comfy but stylish shoes.
I really think you are on your way to a much more tenable situation. I keep finding that women don't really get what they are about until they are at least 35 and it takes most of us until our 40's or 50's to insist on it.
