Large part of wardrobe suddenly impractical

Not too long ago I herniated a disc and while it is substantially healed, heels are no longer something I can wear consistently. Unfortunately my style revolves around heels! I've been wearing them consistently since high-school and switching has been difficult. I love the option of a fun color coordinated shoe to finish off an outfit and heels seem to mesh best with my wardobe. So far I've gotten some platform timberland boat shoes in dark green and converse all star ballet flats. Mary jane flats feel too preppy and standard ballet flats too plain. It's definitely been a struggle to replace my heels for daily wear because I've never really been into sneakers.

Has anyone had a similar issue, where you suddenly found a large part of your style/wardrobe impractical? How did you determine what to replace the items with? Especially if it's something that ​would be expensive to trial and error.