I'm not really a high heel person. But I do have a few pairs of stilettos which I wear occasionally, and a pair of wedges which I find much easier to walk in and more comfortable. I only wear heels when going out (dinner in a bit of a fancy restaurant, that type of thing), so not very often at all.
I usually wear my shoes with dresses, or jeans and a nice top.
However I also have a pair of black knee high stiletto boots, in suede (I got them for Halloween one year as the went great with my fancy dress costume). I usually wear them with skinny jeans, however last time I wore them I was on the train going to visit someone, I had black skinny jeans and a high neck cream jumper on, with the boots, and someone made quite a rude remark about how the boots made me look. Now I know I should just ignore it and not worry. But it got me thinking, are they appropriate with skinny jeans? What else could I wear them with? Any ideas welcome.