Get yourself a pair of
smoking slippers in some awesome color or pattern, something really fun. They are everywhere and are in right now; are flat, and no calf issues.
If you are more casual/fun you could get one of those Tom's classics. Also! Tom's has these awesome wrap boots (just search: Tom's Wrap Boots) that adjust to fit your calf and can go a half-dozen ways. They look great. I can't really wear Tom's shoes because I have a wide foot and they don't make shoes in wide. I know part of it is fat so I still hold out hope, but mostly they just don't accommodate the width of the boney part of my foot.
The wrap boots, though, would be perfect for you. You can wear them as ankle boots or wrap them up your calf, and they will adjust to your calf as you lose weight.