Since no one else has chimed in yet; maybe I can help. Not a woman; but have seen variety of footwear including flats I believe

I have seen heels and other shoes as well if those are more your style/comfort

 

Not sure how to help with the plantar fasciitis aspect, but some brands I like are Margaux (flats), M Gemi (for pretty much everything - flats, heels, mules, sandals, sneakers, booties) and Stuart Weitzman (heels, booties). I think Gucci loafers are comfortable and get a lot of use out of mine. I also have a few pairs of Birdies that are very comfortable and have more cushion, so you may like those. For more affordable options, Sam Edelman and Marc Fisher are also solid brands with a lot of variety. Personally, I prefer heels over flats but you won’t get judged for not wearing them. It’s also very common to commute in more comfortable shoes or sneakers and change into nice shoes at the office.

 

I typically walk to work in sneakers if I’m hitting the gym before/after (makes gym bag lighter) or wear slip on fashion sneakers (I swear by Vinces) and change in heels. Ann Taylor has great heels that are super comfortable, easy to walk in, and pretty reasonably priced. They also have great Black Friday sales so I stock up once a year. Even if you go out for lunch or happy hour, I’ll change my shoes back which is the norm in my office (or maybe I just dgaf...)

 

My girlfriend does the whole sneakers to work thing and gucci/SF flats or heels in the office. Don't do louboutin unless you're going out lol as it gives off a much needed but not office appropriate party vibe

 

Flats / sneakers for the commute into the office and then small heels (always patent black) that I put on once I get there. I swear by nine west heels.... Affordable, durable, and fashionable.

 

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