A Guide to Wearing High Heels for Beginners

We don’t know about you, but we have a love-hate relationship with high heels. While we can’t deny that having that extra height gives us a boost of self-confidence and an instant butt lift—sans squats—life is just not as comfortable standing atop stilettos as it is in flats. Walking in heels, especially if you’re not used to them, can feel awkward and requires some know-how. Lucky for you, that’s where we come in.

Thanks to plenty of trial and error, we’ve figured out what works—and what doesn’t—when it comes to the art of heel-wearing. From the comfiest shoe toe shape to the recommended heel starter height, we’ve gathered our best tips for anyone looking to elevate their gait. So whether you’re a high-heeled newbie or just have been living in your flats as of late and need a refresher, we’ve got you covered.

Keep reading for a guide to wearing heels for beginners, new and born-again.

The Dilemma

Let’s face it: High heels just don’t feel natural—because they’re not. The American Osteopathic Association even states that wearing high heels can cause pain and lead to injuries since it places the body out of its natural alignment. Not to get too technical but elevating our heels increases the amount of pressure placed on the balls of our feet and forces our bodies forward. This throws off our balance, changes our posture, and alters how we walk (read: wobble). Yet despite these adjustments ​straining our bodies, we continue to wear high heels. Pain is beauty and beauty is pain, right? Wrong. The key here is not overexerting yourself since doing so will not bode well for your bod. All it takes is a little practice and patience to go from a clumsy gait to a graceful strut.

The Best Heels for Beginners

No matter how tempted you may be to make your high-heel debut in a pair of gravity-defying Louboutins, don’t do it. The risk of a fall and subsequent twisted, sprained, or broken ankle is high at this stage of the game. That’s not to say that you won’t be able to wear sky-high stilettos eventually, but for now, just ease into it. Here’s how:

Skip the Pointy Toes

Hand with leopard glove holding a pair of round-toed shoes
@brothervellies / Instagram

They can be painful, even for pros. And while there may be a miracle cream to help with discomfort, this can be avoided altogether by simply picking a more suitable toe. A shoe’s toe shape typically comes in either pointy, almond, round, or square, but round is definitely the roomiest and thereby, the comfiest of the bunch. In other words, it’s a heel-wearing novice’s best friend.

Keep Heel Height At 2.5 Inches—Max

Down the road, you may choose to work your way up, but you don’t ever need to—unless you’ve got Lady Gaga’s high-heel ambition, that is. A lower heel will actually make you feel (and look) more comfortable and confident than you ever would teetering on—or falling off—heels that are too high. And while there’s no doubt that a pumped-up platform possesses some type of magical allure, that doesn’t mean that you can’t also find plenty of down-to-earth options that are super stylish. Kitten heels are actually very in at the moment and Lifestride Parigi ($60) makes a killer pair.

Thick Heels Are Your Best Friend…

Woman on a stoop wearing platform heels
@sam_edelman / Instagram

Apart from heel height, heel width and shape are important factors to consider when shopping for a pair of shoes. Block and chunky heels, such as Everlane’s The Day Heel ($58), will offer you the most support while long and thin stilettos are probably best left to the more seasoned heel-wearer (future you, perhaps?). However, if that doesn’t sound sexy enough or dressy enough, look for styles that taper from being wide at the top to slightly less wide at the bottom like Dolce Vita’s Tanika Heels ($60).

…Wedges Too

Most wedges offer a stable base and are a solid heel option if you’re looking for support. Just be sure to inspect them carefully since their shape can vary. To see if they’ll keep your equilibrium in check, turn ’em upside down. If the whole heel is as wide as the upper of the shoe, then you’re good to go. But if it becomes more narrow towards the middle of the shoe, save to favorites, add to cart, but don’t buy—at least not yet. For now, we say stick with wedges like Clarks’s Mallory Berry ($65) for work and Vionic’s Amy Wedge Sandal ($110) for play.

Don’t Forget the Power of Platforms

Wearing heels with a platform in front is a simple, yet effective way to give yourself added height without having to compromise on comfort or style. Sometimes platforms are hidden, and other times not; either way, they all work to maximize your comfort by minimizing the height difference between the ball of your foot versus your heel. These Valentino Garavani Rockstud Leather Platform Sandals ($890) get our Byrdie seal of approval.

Consider Side Adjustments

Nodaleto red platform pumps with black crocodile leather pants
@emnitta / Instagram

Okay, so now that you know what type of heels you’re after, it’s also worth noting their size and fit. If you’re a size 9 in sneakers that doesn’t necessarily make you the same size in heels. That’s because a shoe’s style and material can play into how it feels on your feet. If you’re used to wearing shoes that are more forgiving, say, those with heavy padding or flexible uppers, structured heels—even if they’re the same size—may take some getting used to. You might even need to size up or down to get the right fit. Moral of the story: Try before you buy—or at least check out the return policy.