The trick to wearing heels is finding the right shoe. Avoid shoes with pointy toes. All high heels can be hard on your feet, but cramming your toes into shoes that are too pointy can be extremely painful. A round, open toe or square toe is a much better choice, and much easier to get used to.
Then start off with something lower, and definitely under 2.5 inches. Also, choose a chunky or a wedge heel. They are much easier on your feet. Make sure the shoe is wide enough for your feet.
Always, always, always try on shoes late in the day (your feet swell over the course of the day), and always stand up when trying shoes on - walk around the aisles to see if they cause any pain or discomfort when walking.
When you are comfortable with a lower heel, try something with a more narrow heel. Good luck!
at 5:05 PM on Feb. 25, 2010