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1. Start with a lower 2-3 inch heel and work your way up to 4-5 inches after practicing walking around your home. Shoes higher than 5 inches are really not meant for walking far at all. You will notice that adding an inch to your heel height does make things significantly more difficult, and you may find that a 4 inch heel is the highest you can deal with, but it is different for everyone. The larger your feet are, the higher a heel you will be likely to be able to wear. Several of the most well known models wear a size 11, like Tyra Banks and Paris Hilton.
2. It is easiest to walk in high heels with a bit wider of a heel. They can still be stilettos, just with a bit wider heel like the black and red sandal shown below. Wedges are the easiest to walk in because they have a wider base, and can't get a heel caught in a crack or other obstacle. High platforms with spike heels are the hardest to walk in, and the most likely to make you twist an ankle. Rounded toe, or open toed shoe will be more comfortable than pointy toe shoes. A shoe with a slight 1/2 inch platform will have more padding that single soled shoes, and also adds to the comfort factor.
3. You will find it easiest to walk in high heeled shoes with an ankle strap, t-strap, or other straps to keep the shoe from sliding off. High heeled mules are more difficult to keep on your feet, especially if you are new to wearing heels.
4. Make sure the shoes fit well. If they are too loose, you will have problems keeping them on your feet, and if they are too tight, you will wish they would fall off. It is better to be a little loose, because you can easily add spongy little foot cushions available at most supermarkets and drugstores.
5. Leather shoes will be the most comfortable, will last longer, and will gradually mold themselves to the shape of your feet. They are also the easiest to stretch a bit, should you need to.
6. Watch your step! When walking in high heeled shoes you must be aware of your walking surfaces. Sewer grates, train tracks, stairs, grassy or sandy areas, thick rugs, slippery or rainy surfaces, must all be watched out for. On sandy surfaces you will want to walk mostly on the balls of your feet, like on tip toes to keep your heels from sinking in. When wearing heels and dealing with stairs, always use the handrail, and make sure to have the entire shoe land on each stair, even if you have to turn your feet slightly sideways.
7. While wearing high heel shoes, you should take shorter steps than usual, and as you bring each foot down have the heel touch the floor just slightly ahead of the ball of the foot. Keep your legs close together and walk slightly on your tiptoes.
8. To appear graceful while walking in heels, you will want to keep your feet pointed as straight ahead as possible, and each step should be placed in front of you like you are continually stepping on a single line painted on the floor ahead of you. The famous models catwalk or runway strut takes this a bit further, and each step actually crosses slightly over past the line on the floor to the opposite side. This helps create the sexy hip sway that catwalk models are known for. This does take some practice.
9. Your weakest link are your ankles. You will need to develop strength and confidence that comes from practice in walking in heels and other leg strength development exercises that you will find offered at most gyms. There is even a course called Stiletto Strength specifically for this and the development of poise and confidence while wearing high heels that is available at Crunch gyms.
10. Swing your arms as you walk in high heels which will help with the balance, and add to a graceful appearance.
11. If you are out wearing your heels for an extended period, take them off from time to time, or at least make sure to flex and bend your ankles once in a while to keep them from getting sore.
12. Driving a car in heels is not a good idea, especially in very high heels or platforms. This is even more dangerous with a standard transmission. You can always bring a pair of sensible shoes for driving, and change into your favorite high heels after you arrive at your destination.
13. Never put weight on a high heel that is tilted backwards or you may break the heel.
14. You may find that it helps to walk in heels if you think of yourself walking on tip toes.
15. When turning while walking in high heels, you will find that it is easy to pivot your foot on the point of your heel. This will become second nature to you after a while.
16. If you cannot stand up straight in your heels without bending your knees, then you need to switch to a lower heel. Often just a half inch lower heel can make a big difference.
17. Dancing in high heels takes practice. Practice this at home first. You will also make things much easier if you have some sort of straps holding the shoes to your feet.
18. Wear new shoes around the house a few times to break them in before wearing them outside. This will also scuff the sole a bit making it less slippery on polished surfaces.
19. High heel shoes with lots of thin straps especially in the vamp and toe area may dig in after a short while and become quite painful for extended wear.
20. Don't wear high heel shoes every day. Give your feet some recovery time. If you insist on wearing them every day, at least make sure to vary the heel heights, and if they are leather shoes give them a chance to dry out from any perspiration.