I brought a pair of ankle boots recently. They have about a 2" cuban heel. I wore them to work afew times and only a few people noticed, mostly ladies. Some of them told me they liked them, while others noticed but said nothing. I also had a man say they were nice boots (first time I've had a man comment positively about my heels).
After wearing them afew times I was on my way to work and two boys about 8 years old were in a garden and when I got near asked why I was weating ladies high heels ( they must havr heard me coming). As I was in a rush to get to work I didn't have time for a big discussion I just said they were cowboy boots. They looked at them more closely and one said he liked them and accepted them as cowboy boots.