Reading about stilettos, it reminded me of dangers of thin heel that I have heard of. So, I did a search on "danger of stilettos" and came up with the following.

http://health.learninginfo.org/dangers-stilettos.htm
http://www.youtube.com/watch?v=z80h71oUoHo (Informative Video)
http://www.5min.com/Video/The-Danger...Heel-326754522 (Informative Video), my feet, in hiking shoes, hurt just watching this.

Given that I would vouch for a wider heel and one that is less than 3 inches. Also I prefer to have a softer heel, like, cork.

So, these would be pretty good


These would be fairly supportive


As would these, though taking a half an inch off the bottom would be better


These would be OK, though again taking a half inch off the bottom.

And yes they are Louboutins, for those who were wondering.

Though I prefer something more like this, with knee high or over the knee socks. They are still on my wish list though.