I recently received this email & thought it was a topic that needed covering. I have imparted what I know, but if you have any additional tips, please feel free to let me know via the comments!

Wandering around the city on my lunch break today, I noticed that many girls seemed to be having quite a bit of difficulty walking in their high heels. Have you considered writing an article on how to walk in high heels gracefully &/or with the least amount of pain?A.

Dear Ms. A.,

I know exactly what you mean, & it really hurts to watch. If you’re clomping around like a bad transvestite, the desired effect of looking elegant & glamorous is usually lost. Not to mention, a complete waste of good shoes. You might as well be shlepping around in a pair of gumboots, hey?

Some women think that high heels are for certain occasions only, like going out to a ball or for a fancy dinner. Yes, heels are suitable then, but have a little imagination! You can wear heels whenever you please, & once you know how to wear them, will probably be very keen on teetering around on them.

The main thing to remember is that different situations call for a different sort of heel. Which shoe you wear will depend on where you are going & what you are doing. This can knock the wind out of being spontaneous, but if you suspect that later in the night you will be in a fountain somewhere, you can always slip a pair of flats into your bag. Though, really, if you’re determined enough, you can do anything in your heels. I once climbed a tree (in winter) in a pair of slingbacks with heels that were about 12cm high. (That’s almost 5 inches to you.) Then again, I had been drinking. Great fun though!

Key factors to consider when selecting a shoe for the evening:
The weather forecast. Rain will ruin suede, satin & your evening.
Transport. Do you drive? Catch taxis? What are the chances of you needing to run for a bus or train? If you walk 3 miles every day, a stiletto is probably not your best choice.
Potential hazards. Rain, ice, slippery marble floors, uneven surfaces, deep smooshy carpet, gravel, cobblestones.

Wear something sane! There are some shoes that are only appropriate for answering the door, kissing & walking (or being carried) to the bedroom. Truth. If you’re going to be dancing, I suggest something with a strap. I know that the idea of dancing in heels sounds like absolute torture, but I once danced for 12 hours in a pair of (very high) wedges (with a strap). The next day, my feet were right as rain.

How to buy a pair of heels:

Have your feet measured.

Make sure the shoes fit your LARGEST foot. It is strange & upsetting that we all have two different sized feet, but you need to accommodate the biggest one. (If there is a huge size difference, be sneaky & switch the pairs when your sales assistant isn’t looking. Ahem. I do not advocate this, it is merely information.)

If you’re going out for a day of shopping, do the shoes at the end of the day, after hours of walking around. This is when your feet will be at their most swollen, & believe me, you want your shoes to fit at this crucial time.

When you try the shoes on in-store, walk around on them for a good length of time. Your shoes will fit differently when you stand as opposed to when you are sitting. If they are uncomfortable, don’t buy them. They will not stretch much either, so if they feel like they’re pinching, try the next size up. Stiff shoes will soften, however.

If your toes touch the end of the shoe, & your heel slides out of the back when you walk, they are not the right size.

Make sure your shoe is wide enough!

You get what you pay for. It is sad but true. Manolo Blahnik’s are expensive because, while they are extremely good-looking, they are also incredibly comfortable.

If you don’t know how to wear heels, or have only recently become interested in making the transition from sneaker to stiletto, go easy on yourself. First of all, you are to be commended for trying something new. Hooray! Secondly, when buying your first pair of heels, buy a pair which are reasonably low with a wide heel (or in a wedge style). Otherwise, the odds are that you will go ass-over-tit & never wear them again. We don’t want that. You should also avoid the excessively pointy-toed style, since they’re not the most comfortable.

How to walk in high heels:
Take shorter steps (striding is for professionals), & walk in a heel-toe motion. Try to distribute most of the weight across the ball of your foot. Stand up straight — you will initially feel unbalanced, but you’re not. The heel will support you. Keep your legs together as you walk & try not to bend them more than you normally would.

Finally, practice makes perfect! The more you work at it, the better you’ll be.

Extra For Experts:
Wikipedia has information on the different types of heels (scroll to the bottom).
If your feet hurt, don’t wear heels. It is impossible to be happy when your tootsies are killing you — you learn this one working in retail very quickly.
Never drive in heels, platforms or wedges! Keep a pair of flats in your backseat, or slip your shoes off to drive.
For a good, old-fashioned droolfest.