I am very good at walking in heels, and thank goodness for that as in my opinion- when it comes to heels- the higher the better. My advice: Break yourself in gently; don't start off with stilettos. Try shoes with a chunky heel- it makes things much more stable and comfortable (a couple of months ago I bought some 'Greta' Mary Janes, with a block heel, from Topshop, and they're oh-so-easy to walk in!). Wedges are good, too. Platforms are great because you can get more height but there's less of a slope (thus less pain). In my opinion, you should slowly work yourself up to wearing stilettos- especially the super-high ones- as walking in stilettos is much more difficult as you do wobble about more at first (I did, anyway)... but eventually it just becomes second nature, so don't worry. Pain is almost always going to be an issue- even in expensive, high quality heels I haven't been able to completely avoid pain- but it gets better the more often you wear heels. Always break a new pair of heels in by walking around the house quite a lot before you go out, as then your feet will start to get used to the shoes. If you really are going to be in a lot of pain in a certain pair of heels, try Scholl Party Feet gel pads; I've used them a few times and they do help. The other miracle cure for painful heels is, of course, alcohol. I only wear ridiculously high heels when I'm on a night out, so I don't need to bother about the pain from wearing said heels- alcohol very quickly works its magic on me so I don't feel any pain in my feet at all! Lovely!