Full disclosure: Before I moved to New York two years ago, I wore heels all the time. I’d had the same three pairs of black heels for the past two years, and I loved wearing them out—to work, on dates, to the grocery store (okay, maybe not so much).

When I got to New York, though, I quickly learned that living in a car-centric city in the midwest was way, way more high heel-friendly than living in a large, public transit-oriented city during which my commute was upwards of forty minutes a day (and often spent standing the entire way). I was staunchly (stupidly?) opposed to changing my personal style for mere functionality, though. As a result, I had a brief period of bloody feet, blisters, limping, and constant trips to the drugstore to purchase Band-Aids for my aching tootsies—as well as a shock when I walked through the soles of two of my favorite pairs of heels. It took me awhile to learn what I needed to do in order to wear heels in the city without dying from pain or developing severe foot deformities. But since I did, I’ve stayed ahead of the curve and can sport sexy shoes with the best of them.

(No, seriously: My good friend Mark saw me in flats for the first time in the year and a half that I’ve known him, and he was shocked that a) I wear heels as often as I do without developing serious foot problems, and b) I’m actually shorter than he is. He had no idea because he always saw me in heels!)

Tonight I’m going to share with you everything I’ve ever learned about tolerating heels in a large, pedestrian-oriented city. With a few quick precautions, you’ll be able to wear glamorous shoes all the time without risking soreness, injury, or scuffed-up shoes. Read on!

  • Make sure your shoes fit. Know your size, and don’t buy outside of it. Don’t try to squeeze into a smaller one just because they don’t have your size—you’ll be headed to blisterville and might even develop heel spurs or plantar fasciitis (nasty and painful!). And wearing shoes that are too large for you will mean long days of faceplanting in the street whenever your feet slip inside them. This is a huge temptation when you’re a seven and you find the perfect pair of vintage boots in a six and a half, or when that pair of Jimmy Choos on sale is too narrow for your prominent tailor bunion. But don’t be tempted. You’ll merely end up miserable, and not only will you be unable to return them to the store, you might endure enough pain to swear off heels forever. It’s worth noting, also, that every brand and style fits differently. So, don’t buy shoes without trying them on. (Come on, do you ever buy a piece of clothing without trying it on? If so, shame on you! You should stop now!)It’s also worth noting that your feet can change size. Your feet swell as the day goes on, so some people end up wearing a full half size bigger in the evening than they do in the morning. (This is why it’s smart to go shoe shopping in the evening rather than the morning!) Also, heat and cold can cause your feet to expand or contract seasonally—I definitely have a pair of amazing vintage white cowboy boots that I can’t fit into during the summer, because my feet are too big! Finally, events like injury or even pregnancy can cause your feet to change size or shape—so beware! Always try your shoes on before buying. You’ll thank me.
  • Take care of the shoes themselves. Inspect your heels often. If you’re like me, the little rubber tips at the bottom of the heels will wear off over time, exposing the metal posts in the heel (called the taps). When this happens, take them to the cobbler right away and get them replaced—if you don’t, you risk ruining the whole heel of the shoe and marking up the leather. Likewise, check the sole for excessive wear, and the heels for instability—you can have both fixed. If they’re real leather, clean and polish them often, especially after they’ve gotten particularly dirty—this will keep the leather in good shape for a long time, ensuring against cracking, peeling, or excessive scuffing. And finally, wear the correct size! If you wear shoes that are the wrong size, they’re going to wear out more quickly!
  • Buy good shoes. This pains me. But it’s the truth. If you continually buy poor-quality shoes, you’re paying for badly-constructed, thin-soled, ill-fitting, weak-heeled shoes. So stop. If you’re on a budget, save for one or two good pairs of versatile heels rather than ten pairs of cheap ones. If you have an addiction and require a constant influx of new shoes, frequent the discount stores like Daffy’s and T.J. Maxx, as well as discount online shops like 6pm.com (this is the overstock site for Zappos)—they’ll cure what ails you.
  • Take care of your feet. Clip your nails and file them down–sharp corners can dig and cause blisters. Also, if your feet sweat a lot, coat them with a little bit of baby powder before you put your shoes or stockings on, or wear those teeny pantyhose-like socks inside your shoes if you think it’ll help. Soak sore feet in a warm tub of Epsom salt (which I recommend for any kind of muscle soreness!), and it goes without saying that if your feet are injured, DON’T WEAR HEELS, damn it.
  • Break them in. Wear them around your house while you do some lightweight chores, or while you’re having some friends over for tea. They’ll mold to your feet, and if they start hurting you, it’s easy to kick them off and go barefoot for awhile (as compared to, say, on the subway—come on, do you really want to put your bare feet on that nasty subway floor?!)
  • Know how your feet behave and anticipate any rubbing that you know is going to happen. I personally have little bumps on my heels left over from years of squeezing my feet into pointe shoes. As a result, this is the first place I get blisters—so as a result, I habitually bandage my heels with clear adhesive tape or Band-Aids before I step into my pumps. If your toes habitually crunch and rub blisters on one another, try a set of toe spacers—I used these when I did ballet, and they’re great for stopping blisters on the sides of your toes. Keep in mind, though, that some of these issues are merely caused by poorly-fitting shoes, so I repeat: don’t wear shoes that don’t fit you!
  • Don’t wear heels seven days a week. No matter how well they fit and how diligently you take care of your feet, heels are kinda bad for you. If you wear them all the time, you’re just asking for chronic problems with your ankles, knees, and back. Plus, you’re much more likely to sustain acute injuries while you’re wearing them—sprains, strains, and fractures, as well as trips and falls that can make you skin your hands and knees like a schoolgirl. Give yourself a break—designate every other day or every third day as a heels-wearing day, but the rest of the time, opt for ballet flats, oxfords, or flat boots.
  • Don’t commute in heels.It’s one thing to wear your amazing peep-toe t-straps all day when you’re sitting at your desk or padding around the carpeted office. It’s quite another to wear them for your six-block walk to the subway and your five-block walk from the subway to your house. So don’t. The same goes for going out—wear your killer gladiator heels at the bar, but tuck a pair of cute, comfy flats into your bag for the tipsy train ride home. (Plus, let’s be honest: If you change out of your heels during a long night of drinking, who’s going to know? Everyone around you will likely be drinking too. And you might save yourself some trouble—drunk walking in heels can result in injuries and severely distressed-looking shoes. Trust me.)
  • Do your best not to wear heels in rain, snow, or ice. I know this isn’t always possible to predict, but use some common sense. If it looks like rain, bring an umbrella and flats. Or, better yet, wear boots and change your shoes when you get where you’re going.
  • Learn to walk in them properly. Having been a dancer, I am one of the rare breed that can run in heels. Walking on my toes is natural to me, so it’s no feat of strength. However, if you’re not like me, you should watch this video. It instructions you on how to walk in heels confidently and safely, and I really can’t do any better than that.
  • Bring band-aids, invest in some Epsom salt soak, and have a drink. Because, at the end of the day, there’s nothing you can do to make heels one hundred percent comfy one hundred percent of the time. So do your best, but be aware that it can all go awry.

Do you guys have any really harrowing heel-wearing experiences? Or, how do you make heels more comfy and practical?

Related posts:

  1. How to Make Heels Bearable
  2. How to Make a Style Inspiration Guide
  3. Inspiration: 1.27.2009