I can walk with heels as long as they are not higher then 1-1,5 inch (So no high heels.), as well that they must be broader heels, so no pencil-broad-heels/stilettos. As well that they need to fit rather well on my feet, as example with some band around the ankles (or full boots ...), so that your foot is not loose in them.
But beside rather few occasiones, I dont really wear them. Around here its custom to remove your shoes when entering someones flat/house, so for visiting friends its stupid, for cinema its as well stupid, bowling anyway... So beside stuff like "father in laws 60ies birthday in an restaurant", there is no real use in wearing these. (And I am not really sad about it. ^^), and I only have two pairs of them.
When visiting concerts, I like to wear my heeled booths, so I am rather small compared to the average man size, so 1-2 inches more, can help pretty much.