Holy Sh*t, I Can't Believe Girls Have To Walk In These Things

by Joe Oliveto
Joe Oliveto

I'm your typical American dude. Please accept my apologies. (I'm not sure what I'm apologizing for, but I am sure it's something.)

As your typical American dude, there are some experiences I'm not likely to ever have. Dealing with “that time of the month.” Being catcalled. Liking Carrie Bradshaw.

And I think we can safely add “walking in heels” to that list. Aside from that one weird dream I had that time in college, my experience with wearing women's shoes is fairly limited.

Me and my "How 2 Walk In Heels" classmate

Because I'm a guy, my footwear tends to be only marginally less comfortable than a pair of slippers. It makes life pretty easy. If I'm heading out to the mall and can find a parking space two miles from the entrance, the idea of a long walk doesn't bother me.

If the elevator at work is out of service, I'm not intimidated by the stairs. And if I'm ever stumbling around, that's just because I'm painfully awkward and uncoordinated -- not because my shoes were designed to make me look like I'm bombing a field sobriety test.

So, naturally, I was a little/a lot terrified when my editor asked me to attend StripXpertease's “How 2 Walk In Heels” class, and not only because I've lived behind a strip club, and it was a nightmare.

But I'm interested in any opportunity to step outside of my comfort zone (or, in this case, my comfort universe) and see what kind of challenges other people face.

It was … educational. I'd like to thank the wonderful people at CourseHorse for setting everything up.

(True story: The day after they signed me up for the class, my mom texted me to ask if I'd heard of CourseHorse. Little did you know, Mom...)

Although, speaking of my mom…

Step 1: Buying heels

The folks at StripXpertease, for completely understandable reasons, do not provide you with heels for the course. This is not a bowling alley. You have to bring your own.

I do not own any heels. When I hear women talking about shoes, I have such a hard time understanding their words that I kind of worry they're having a stroke.

I also don't know how to buy heels. I suppose I could just head to a store and try them on until I find a pair that works. But I'm a shy person, so doing that would require consuming an amount of alcohol I haven't had since I was an undergrad.

Luckily, my family's annual Easter brunch was right around the corner, giving me the perfect chance to ask my mom to help out in this area.

She enthusiastically agreed, which was really cool. I mean, when she and my dad were putting me through college, they couldn't have imagined this would be how I'd end up earning a paycheck.

Heels purchased with my mother's help

Step 2: Home practice

The class I'd be taking was originally meant for women only -- thanks again to CourseHorse and StripXpertease for turning it into a co-ed experience -- and I suspected I'd be the only guy there.

(Spoiler alert: I was correct!)

I also suspected I'd be the only one there who was ridiculously bad at this.

(Spoiler alert, part two: Yes!)

I'd accepted that I was going to embarrass myself. That was no big deal. Again, I'm an awkward guy; I accept that I'm going to embarrass myself every day.

That said, I wanted to at least give myself a chance to minimize my humiliation. That meant giving the heels a test run at home before the big day. How do you think that went?

(Spoiler alert, part three: YOU KNOW HOW IT WENT. STOP LAUGHING AT ME.)

Step 3: Introductions

Heels in hand, I arrived at the class on a Friday evening and met Abby, the super helpful instructor. Three other women were there for the lesson. Abby asked us to introduce ourselves, and while I was quick (probably a little too quick) to point out that I was a writer on assignment, my fellow classmates all expressed a desire to learn how to be more comfortable walking around in heels.

They weren't there to learn how to look sexy while strutting down the catwalk or seductively cross a room without missing a step. These women just wanted to get some tips on how to handle a night on the town without feeling like they'd hiked Everest by the time their heads hit the pillow.

I have never had this concern. In college, I stumbled back from parties all the way across town because I couldn't wait for a sober friend to drive the two minutes from campus to come pick me up. In Manhattan, I'll walk half the length of the island to avoid lingering in a subway station for more than five minutes.

I mean, I'm not graceful, so I'm always kind of concerned about how I look when I walk. But I don't care that much about how I feel.

Step 4: Learning the language

Stiletto. Wedge. Platform. Kitten. Pump. Mule. Cone.

To me, that string of words sounds like slam poetry. Apparently, though, these terms are actually quite important if you're looking to select the right heels.

When I'm buying shoes, I'm concerned with three things: Whether or not they fit, whether or not they're affordable, and whether or not they make me look stupid. And, to be honest, that third one isn't that important.

Choosing heels, I've learned, is a bit more complicated. As Abby walked us through the pros and cons of each option, I began to feel like I was back in high school, struggling through Spanish class and furiously taking notes to make it look like I understood what I was hearing.

Step 5: Gadgets

Heels were not designed for comfort. They were not designed to help you run faster. They were designed to make women look attractive -- and also to embarrass short boyfriends.


Luckily, there are ways to alleviate the pain associated with walking on a shoe that could double as a crude torture device. Abby shared them with us when she unveiled a collection of gadgets more impressive than Batman's f*cking utility belt.

She had foot pads, cushions, and grips to protect the balls of your feet; roll-up ballet flats for the end of the night; lamb's wool and adhesive tape for blisters; lotion and rollers for your recovery. And that's barely half of it.

I'll wait too many months before I bite the bullet and replace my frayed shoelaces. I usually defer to the wisdom of Morgan Freeman in “The Shawshank Redemption”: “I mean, really, how often do you look at a man's shoes?”

As far as I'm concerned, spending any extra cash on your footwear is appropriate only after you've won the lottery and have run out of other ways to waste your money.

Little did I know, if you're going to walk in heels regularly, you may need to splurge on some extras just to manage the discomfort.

Step 6: Exercises

When I agreed to take the class, I didn't know I'd be having flashbacks to my embarrassing stint as a yoga student.

Our teacher began with some instructions: Write the alphabet with your foot to strengthen your ankles. Wiggle and slap your foot to release tension. Pick up a pencil with your toes. Stretch your Achilles. Roll your toes one at a time.

Abby was full of useful advice. She ran down the numerous exercises you can do to make walking in heels much more manageable.

Except I'm not used to doing any sort of exercises in order to deal with the simple task of walking. I can barely be bothered to maintain decent posture. I didn't expect to go through boot camp just to feel comfortable in a pair of shoes.

I once got mildly annoyed at my senior prom date for complaining that I parked too far away from the venue. If you're reading this (you're not), I'm so, so sorry.

Step 7: Humiliation

After getting a rundown of the major life changes we'd have to make if we ever hoped to feel comfortable in heels, it was time to actually put our shoes on.

I pinched myself to make sure I wasn't having a nightmare. No luck.

We started off by trying to balance on one leg. It took me about 30 seconds to go from laughing at myself to “I'm not crying!”

Next, what Abby called “Kate Spade Kicks:” We kicked our feet to the side, like a cat with tape stuck to its foot. I've always adored cats.

Maybe I don't anymore.

After that, we did jumping jacks, which, according to the cheat-sheet Abby gave us at the beginning of class, increase “balance and confidence.”

Hahaha. NO.

And then, it was time to speed-walk across the room. I didn't fall down, so I'd call this one a success.

Then, there was the “Prada Pivot,” which involved walking fast across the room, performing a sexy 360-degree twirl, and continuing to walk as if we hadn't just performed an Olympic gymnastics routine.

I did not do as well on this one. I used to feel bad for Gisele because she had to live with Tom Brady. Now I had got two reasons to pity her.

Finally, we were supposed to do a "calm, confident walk" -- as if we were "strutting" down the street.

"Calm and confident" are definitely not qualities of mine. Whatever. I mean, it was fine. Don't worry about it.

Step 8: Reflection

The last time I learned to walk, people still thought the VCR was mind-blowing, “The Simpsons” was still funny, and people were excited to see Guns N' Roses for non-ironic reasons. Spending an hour on something I take for granted every day was humbling. I learned a lot, and I managed to survive with some semblance of dignity intact.

But I also realized, in a pretty visceral way, that women are expected to put themselves through physical discomfort, embarrassment and a plethora of other unpleasant feelings just to live up to society's standards.

Again, as a typical American dude, I'm allowed to fully adopt a do-what-you-want attitude when it comes to how I present myself to the world. As long as I'm not breaking any laws, I can wear what I want and prioritize my own comfort. I'm not committing a faux pas by deciding that I'd rather not torture my lower body in order to appear attractive at a social event.

I want to be clear on one thing: I'll never know what it is like to feel as though I need to master a skill like walking in heels. For me, this experience was a novelty, one I can write off quickly. No one expects me to be good at this.

That's not the case for women. Sure, you can rebel against expectations, but that will automatically be seen as some sort of statement you're making. If you simply decide that you won't wear heels, you defy what society expects of you.

Or, at least, I assume that's the case. The truth is, I don't know what it's like to feel that pressure, and I never will. Taking this class did for me what great education should do: It gave me such a unique perspective that I realized how much I still have to learn. I could try to mansplain it all (and I probably have, without realizing it … again, sorry), or I could deal with the fact that I don't know what I'm talking about. An experience like this doesn't change that; it simply makes that fact even clearer.

That said, I have never been happier to put on sneakers.