Eh. I've been in flats daily for essentially my entire life - from high school, right through undergrad and now, into med school and hospitals. AND IMHO, many women (including myself) have made them work with every outfit we own.
Heels were never my day-to-day wear after I looked at an image that showed how pressure points and intensity changed between walking barefoot, in flats, sneakers and heels. There is nothing "contrarian" about not wanting to ruin my feet with non-stop blisters or mess-up my MSK structure to look "acceptable" in the eyes of, mostly, men?
They were and always will be special event shoes - date night, weddings, parties, a night out etc. and even then, more often than not, I'm in flats.
As for sartorial and social approval, never needed that; but I (rightly or wrongly) credit a lot of the "sneakers" movement to Phoebe Philo. She brought Stan Smiths back into the spotlight as a feminine option by wearing them consistently and comfy (but stylish) boat-type shoes into the brand. Far too many other designers - male and female alike, either wear heels for all their appearances or happily send their models tittering down the runway in sky high heels or both.
