As a freelance I have the good fortune to work from home and so can wear what I please. My wife, who does not wear heels, neither approves nor strongly disapproves - she seems to consider it a reasonably excusable foible on my part. I do not wear heels out on assignment, mainly because the remote places I tend to go they'd be utterly inappropriate, if not dangerous, footwear. Also in the past year I've been living off-grid in circumstances where heels would be almost comically inappropriate footwear whether you were man or woman. But when I am put and about I do wear lower heeled knee boots (with sturdy soles) just about everywhere. And when I'm at my desk, in my home office, heels are definitely part of my office dress code!