I could write a book on shoes and how to wear them. With so many factors like, height, length of leg, comfort, practicality and age, finding the right shoe isn't as easy as it seems. They can totally vamp up an outfit but they can also take it down in flames. Here are some rules I follow and hopefully some can apply to your life as well.
1. Never wear mules or clogs. Orthopedic doesn't equal accessory. Those are work shoes for nurses and chefs-they have no other purpose, even if you think they do. Have you ever seen a spread in Vogue-"Top Mules for Fall!" No you haven't.
2. Wedges are tricky. I think if you wear them under wide leg pants or with a sundress in the summer than you might be ok. BUT they are essentially wood bricks. So if you have short legs, you could really shorten your appearance rather than elongate.
3. Kitten heels are for wusses. What's the point? Wear flats if you can't wear heels. A kitten heel is a rip off and a fraud, I detest.
4.Thigh high boots are for no one. I love them, I wish I could wear them but you end up looking like a hooker and unless you have skinny knees and legs, you actually look like you have a leather cast on.
5.USE cushions whenever possible. I feel empowered by heels, mostly because I can rise above others armpits-but running around in them hurts and carrying around sneakers is annoying. I found if I order my heels a half size bigger, then put in gel insoles or even custom made supports, I beat the system.
The best bit of advice I can give is to find a heel height that suits you and buy in a variety of colors and fabrics. If you're comfortable with the heel height you will be more open to wearing them often. You should buy open toe and close toe and pointy and ankle strap-go crazy. You don't need to change with the trends you just need to make sure you have enough variety in your closet so you don't stray and buy some god for saken clogs.