Closet Case: Hell on High Heels

Even if they look like torture devices, you don't have to think of them that way.

You know how everyone has that one question that they get from people – coworkers, friends, random strangers on the street – all the time? For me, that question is “How do you walk in those things?” I hear some variation of it at least once a week, and my answer is always the same: practice.

I know that many of my readers are already seasoned pros at beating the streets in five-and-a-half-inch platforms, so if you’re one of those, feel free to skip this post altogether. However, I’ve had a lot of people, both online and in my real life, asking me for tips on getting acclimated to wearing heels, so I’m going to give you guys the lowdown.

First off: Get over it.
Before you do anything else, you need to get over whatever fears or issues you have that have kept you from wearing heels in the past. I don’t want to hear about your fallen arches or your foot problems – I have flat feet and bunions and I do it on the daily, so you need to throw all that bullshit out the window post haste.

You either want to wear heels or you don’t. If you want to, you have to stop making excuses and just start doing it. (And don’t psyche yourself out by thinking about the long-term effects of wearing them or else you’ll scare yourself off them forever. Trust me, one day soon you will view your foreshortened Achilles tendon as a badge of honor.)

And about that whole "comfort" thing.
Let me say something else here before we go any farther. One of the most common complaints I hear from friends when they’re shopping for heels is that they aren’t “comfortable.” Listen: high heels are not comfortable. They will never be comfortable. You are forcing your feet into an unnatural angle and supporting most of your weight on what is essentially a big metal nail. There is nothing comfortable about it.

When women talk about heels being “comfortable,” we are speaking relatively. There is no such thing as a shoe that “looks like a pump but feels like a sneaker,” and if there is, it is probably totally ugly and made by Aerosoles or something. If you are looking for comfort, there is no shame in a flat. If you are looking for leg-lengthening, confidence-boosting, man-luring, height-enhancing ultimate sexiness, you’re going to have to be willing to sacrifice a little comfort.

But listen, readers, and heed my words: IT WILL GET BETTER. You will learn. You will become accustomed. And one day you, too, will find that you have become one of those infuriating, amazing women who point to their five-inch snakeskin stilettos and say blithely, “Actually, they’re surprisingly comfortable.”

Second: Going for it.
Get thee to a big department store and try everything on. Learn what brands and styles you like best. Do not have qualms about asking to try on $700 pumps, even if you have only $7 in your wallet. It’s about figuring out what works. A few rules of thumb for shoe shopping:

• Most shoe departments and stores are carpeted, which is a sneaky way of tricking you into thinking that what you are trying on is more comfortable than it actually is. It’s easier to walk in heels on carpet than it is on a hard surface, so make sure you do a lap on the tile as well. If the store you’re in doesn’t have any hard floors, ask a sales rep if you can step outside for a minute to experience how the shoes are really going to feel. They should let you, and if they don’t, you should go somewhere else.


• Just like clothes, the sizing in different brands of shoes can vary wildly, plus some companies don’t make half sizes, and higher end brands tend to be in European sizes. Get familiar with how your favorite brands fit. Learn what your European size is (here’s a conversion chart), and if you’re a half size, figure out whether you tend to go up a size or down when wearing whole sizes.


• Shopping online is a little trickier because you can’t try things on. It really helps if you’re already familiar with the brand you’re ordering. Whenever possible, order your size and the next size up or down. Then you can just send back whichever pair doesn’t fit. A lot of shoe sites, like Zappos and Endless, have free returns for just this reason.

A note on height.
One of the most commonly prescribed tips for wearing heels is to start small and work your way up – the baby steps theory, AKA “Oh, well, I’ll start with a kitten heel and soon I’ll be ready to go up to three inches and then after that I can start going for five inch platforms!” I understand the reasoning behind this logic but frankly I don’t think it’s 100% sound.

The first reason is that whether you like it or not, sky-high heels are the trend right now and they are only getting higher, so you’re going to be hard-pressed to find anything you actually want to wear that’s lower than maybe 3½” inches. (Not to mention the higher the heel, the better everything looks.)

The second reason is, why draw it out? No matter what height you’re wearing, if you’re used to flat shoes a high heel is simply not going to be comfortable. Using the baby steps method forces you to get used to a 2” heel, then a 3”, then a 4”…boring and unnecessary. I say pick the height you want to be wearing, find a pair that’s comfortable enough for you to wear for at least a couple of hours a day, and just get used to them. This is why platforms are a girl’s best friend.

Third: Walking the walk.
First you have to get acclimated, and I’m sure you already know this one: wear them around the house. Constantly. Put them on as soon as you walk in the door and leave them on until you can’t bear another second…then leave them on a little longer. Wear them while you are making dinner. Wear them while you are doing laundry. Wear them while you are blowdrying your hair. If you have roommates they might laugh at you, but if you live with your boyfriend or significant other, you can tell him to e-mail his gratitude to waitinround@gmail.com.

Now, about the actual walking you are going to be doing. Wearing heels requires making adjustments to the way you move. You have to be conscious of what your legs and feet are doing or else you will find yourself turning your ankle or tumbling to the ground with humiliating quickness, not to mention there are few things more distressing than a woman in incredible high heels who doesn’t know how to walk in them. I will not stand for any of you tromping about like Bigfoot on my watch, so, a couple of pointers:

• When you walk in flat shoes you put your heel down first, and when you wear heels you’ll still be putting your heel down first, but while focusing more weight on the ball of your foot than on your heel. Anchor your toes by pressing them against the insoles of your shoes if you must. Take smaller steps than you would in flats.


• Your posture is super important, as wearing high heels puts your center of gravity off balance. If you are leaned too far forward when you are walking in heels, you will look like Lurch, so please, please, for the love of god, back straight, chest out, shoulders back, and, most importantly, head held high. You are going to look tall and lean and long and amazing, so don’t fuck it up.


• You also want to get a little bit of that catwalk swivel thing going – you want to put your feet slightly in front of each other with each step, so your footprints form a single line, kind of like you’re walking on a balance beam. You don’t need to overdo it and start stomping around like Karlie Kloss or anything, but putting a little hip into it will make your stride more elegant.


• And, honestly, the stronger your feet are, the easier you will find it to walk in high heels – I took ballet for years so I credit Mme. Price of the Royal Academy of Dance with a lot of my ability! This sounds stupid, but if you are really committed, some foot-strengthening exercises would be incredibly beneficial. Here is a short video of some simple foot exercises meant for ballerinas; even silly things like picking up marbles with your toes will help.

Finally: Taking them out.
When you’re ready to start wearing them out and about, ration them a little bit. Think about where you are going. Will you be on your feet for more than a couple of hours? Will you be able to sit down if you want to? Will you have to make a long trek to your car at the end of the night? (Remember, what feels comfortable at 9:30 is not going to feel quite so good at 1:00.) Answer these questions and then decide whether or not you’re ready to be heeling around. Movies, house parties, and dinner dates are good places to start. Then you can start wearing them to work (well, if you have an office job like me where you get to sit a lot), and after that you’ll probably be ready to wear them out to the bar or the club. You might even be ready to dance in them, and if you’re not, you will be soon!

One more word on comfort.
I said that heels aren’t comfortable, and they aren’t, but that doesn’t mean there aren’t measures you can take to make them way more tolerable. The first and easiest is to be aware that, typically, the more a shoe costs, the better it’s going to feel to wear it, but that doesn’t mean that cheap shoes are necessarily painful (I actually find that Forever 21’s shoes, for instance, are pretty decent). Still, I highly recommend being in possession of an arsenal of items that can make your life in heels a lot more comfortable. Here are a few of my favorites:

1.) Dancers stuff lambswool into their toe shoes to provide cushioning and comfort. You can put it into the toe box of your heels to keep toes from sliding forward or to cushion a shoe that's a little too wide. Capezio lambswool, $6.95, On Stage Dancewear.

2.) Dr. Scholl's makes a wide variety of insoles meant to make high heels more comfortable; my favorites (even for closed-toe styles) are the Open Shoe Insoles, which have a thinner profile and a more satiny feeling on the foot. If you can afford to, you might as well put a some type of cushioning insole in every pair of heels you own. I especially like this type for inside boots and lace-up styles, and they're good for cheaper brands that use cheap lining material. Dr. Scholl's For Her Open-Shoe Insoles, about $9 a pair, drugstores.

3.) For slingback straps that rub, peeptoes that chafe, and so on -- you can rub Blister Block directly onto your skin anywhere that your shoes are rubbing and it'll provide friction that keeps blisters from forming. I always have this in my purse; it's great for flats too. Band-Aid Activ-Flex Blister Block Stick, about $5, drugstores.

4.) If you're willing to spend a little bit more, Foot Petals has pretty much every type of cushioning insole you could possibly want. My favorite are their Tip Toes ball of foot cushions, which keep feet from sliding forward and do away with toe scrunching. Tip Toes metatarsal pads, $7 for a pair or $19 for three pairs, Foot Petals.

5.) For persisently annoying slingback and sandal straps, I like this little dispenser of cushiony foam tape, which you can fit on the inside of problem areas to do away with rubbing, and which peels off without damaging your shoes. Dr. Scholl's For Her Rub Relief Strips, about $7, drugstores.

6.) When all else fails, even a die-hard heel wearer like yours truly has to admit it's always good to have a backup pair of flats that you can throw in your handbag or tuck into your glove compartment. This roll-up style, designed just for high heel emergencies, is cheap, surprisingly cute, comes with a handy little pouch to tuck them in, and comes in an assortment of colors -- they even make pairs with Louboutin-style red soles! Roll-up ballet slippers, $25, Footzyrolls.

The final word.
Look, above all else, wearing heels comes down to little more than practice and a willingness to be a little uncomfortable. The more you wear them, the easier it will be, but no matter what there will always be days when your feet feel like they’re about to fall off and you’d kill someone for a pair of ballet flats. But that’s the way it is – we have to suffer a little bit for fashion sometimes. Do not swear off platforms the first time the balls of your feet go tingly after a long day on foot – take it as a point of pride. Now you can do something that tons of women cannot, or will not, do, and when people ask you how you walk in those things, you can just smile and say “Practice!”