Some time ago in a local shopping centre dining place I happened to saw a woman around her 40s wearing thigh-high stiletto boots, about 3,5-4 inch heels, and inside them long athletic pants. These ones are really suitable for jogging or sporting outside, but this one wore them under a nice looking pair of heeled boots
Otherwise she looked elegant, but all my friends suspeced she was a pro (hooker) taking a break... and forgetting about other pieces of clothes besides her heels.
I think normal pants with thigh-highs are OK, but sport outfit with heels
I just wish I had had a camera with me at the time...