A Guide to Wearing High Heels for Beginners

Moving From Sneakers and Flats to Heeled Shoes

Chic black pumps with suede uppers, almond toes, and 2" wrapped, chunky heels.
With wide 2" heels and almond-shaped toes, stylish pumps like these would be the perfect shoes for high-heel novices and seasoned veterans alike. Cole Haan 'Chelsea Low Flared Heel' Image: Zappos.com

So, you've got a special event coming up. A job interview or a wedding. If you're a teenager, maybe it's your first prom. For whatever reason, you feel as if you really should wear a pair of high-heeled shoes.

There's only one problem. You're not really comfortable in high heels because you just don't care for them. Perhaps it's been a really long time since you wore anything but flats or sneakers.

Or maybe, you've never worn heels before. And now you've decided that you kind of like the idea. You want to shake things up. Change your image a bit. You're allowed. Right?

Damn right.

And I've got even better news for you. A) It's not as scary/weird/awkward or uncomfortable as it might seem, and B) it doesn't really matter whether you just need a refresher, or you're an absolute beginner when it comes to wearing heels.

Not a single person I know of came out of the womb wearing heels. And, no matter how elegant, natural, or graceful so-and-so seems in her stilettos, she too had her first time. If she can do it, you can do it. What's more, you won't look ridiculous doing so.

First things first, banish all thoughts of B-list celebrities in sky-high platform pumps, or statuesque models strolling down the runway in 5" heels. While you're at it, get rid of any mental images that involve strippers, prostitutes, drunks or chavs.

And before you strain your imagination trying to come up with a friendlier image of women in high heels: stop!

This is you we're talking about. Your tastes. Your wardrobe. Your feet.

Now, let's get those feet of yours into some heels.

But High Heels Don't Seem Natural

That's because they're not. We weren't born with spikes coming out of the bottom of our feet, so it's absolutely not going to feel natural at first.

In all honesty, you may never be comfortable in extremely high heels.

That's ok. In fact, it's better than ok; it's actually a good thing.

It's well-documented that wearing high heels too often or for extended periods of time can cause short- and long-term pain in our legs, knees, back, feet, and ankles. Not to mention the risk of injury that comes with just by walking in a pair of heels.

High-heeled shoes force our bodies into uncomfortable -- and unnatural positions. Elevating the heels of our feet increases the amount of pressure placed on the balls of our feet and force our bodies forward. This throws off our balance, changes our posture, and it alters the way we walk. Needless to say, all those adjustments, especially at once, ​put a strain on body parts we might not be used to straining.

Having said that, a lot of women do, and will continue to, wear high heels every single day. You might too. You don't have to. It's your call. But, if you're ever going to attempt wearing heels, you need to start the right way.

That means slow and steady.

It means not causing yourself pain.

All it does mean is that you're going to ease your way into shoes that may not be quite like the ones you're currently wearing but also aren't all that different.

And that is a lot less scary. In fact, it's not scary at all.

The Best Heels for Beginners

Read this: Do NOT attempt to wear extremely high or thin heels your first time. Now, make a promise to yourself (and to me) that you're going to follow that advice, and use the suggestions below to choose your first pair of heels.

  • Skip the pointy toes! They can be painful, even for pros. You certainly don't need that kind of X-factor at this stage in the game. A shoe with a round toe is the beginner's best friend.
  • No heels over 2.5 inches. Down the road, you may choose to go higher, but you don't ever need to. And, for your first pair, you definitely shouldn't exceed this limit. There is no reason to. You can easily find evening shoes and casual shoes with heels lower than this. And, starting with a lower heel will actually make you feel (and look) more comfortable and confident than you ever will teetering on -- or falling off -- of heels that are too high.
  • Block or chunky heels are best for heel novices.
  • If you simply must have a dressier heel, look for styles that taper from being wide at the top to slightly less wide at the bottom. Avoid heels that are skinny and straight or any that are very thin at the bottom tip.
  • Wedges - Wedge heels might be a good option, but you'll have to look at them carefully to be sure they'll provide the proper balance. Turn the shoe upside down. If the whole heel is as wide as the upper of the shoe, then it will make for a good first heel. If it becomes more narrow towards the middle of the shoe, skip it for now, and stick with one of the other options listed above.
  • You Might Need a Different Size - Even if you're always, always, always a size 9.5 or 7, you should still try on your first pair of heels before buying them.
    Two reasons. First, some styles of shoes are more forgiving than others. So, if you are used to wearing sneakers, you might not realize that you actually need a 9.5 wide or narrow. Also, if you're used to shoes that have a lot of padding or more flexible uppers, you may find you're not quite as comfortable in more structured shoes, even though they're the same size.
    If can only find the shoes you really want online. Try checking out a similar style from the same manufacturer in person first. As a last resort, be sure that the site you're ordering from has acceptable return policies.

Moving On Up

Once you've found a pair of comfortable heels that you're not terrified of walking in, follow the steps outlined in this tutorial for Walking in High Heels.

When you're confident enough in your new heels, you can gradually move up in height, and begin thinking about different shoe and heel styles -- assuming you want to. We're fortunate enough to live in an era with such variety that women shouldn't feel confined to wearing any specific style.

If you're happier where you're at now, take comfort in the fact that you'll probably save yourself loads of possible pain and problems down the road.