Let’s Roll

Field-testing Heelys, the sneakers with wheels.

You probably know what Heelys are even if you’ve never heard of them: They’re the sneakers with wheels in the heel, the ones that allow kids to transition from a walk to a roll with unnerving ease. You’ll be keeping pace with what appears to be a normal, ambulatory youngster when all of a sudden he’s gliding ahead, weaving effortlessly through foot traffic. For those of us who came of age in the rollerblade era, this can be a discomfiting experience—we’re not used to recreational footwear that doesn’t advertise itself as such. We’re also, I suspect, a little bit envious. In just the last couple of years, the shoes have become wildly popular with kids—Heelys Inc. had $188 million in sales last year, up from $21.3 million two years earlier—but most adults don’t suspect that you can get Heelys above a size 5. It turns out you can. So I decided to get a pair and see what we’ve been missing.  

Easier said than done, actually. You can’t buy Heelys directly from the company, so you’ve got to go hunting at Zappos, the Sports Authority, Modell’s, and the like, and the pickings in the adult sizes tend to be slim. Then there is the question of aesthetics. Heelys come in about 30 styles for men, ranging from reprehensible (what can brown on brown do for you?) to still pretty bad. Most of the models are designed to look like skate shoes, though a few resemble Nike trail runners.

After searching high and low for a reasonably appealing pair in my size, I gave up. I settled on two possibilities: one a somewhat innocuous blue and white pair that I thought might pass for something in the Adidas tennis collection, the other an egregiously ugly number featuring perforated leather, faux-suede, and reflective trim. I was hoping the innocuous pair would pan out, as I thought they’d allow for an element of surprise—those are Heelys?—but when the shoes arrived, I saw they were innocuous only by comparison. Heelys are by necessity a bulky shoe, as the heel needs to be deep and wide enough to house, essentially, a skateboard wheel. No one was going to mistake these clodhoppers for my trusty Rod Lavers.

The ugly pair, on the other hand, were charmingly so. An enormous, ketchup-red Heelys logo adorned the flank of each shoe. A graffito on the tongue challenged the reader to “Grind This!,” a directive the midsole backed up with an obsidian grind plate. My choice was made.

Before describing the “heeling” experience—Heelys owners, like good dogs, are said to heel—it’s important to dispel what I’ve found to be a common misconception. Like many heeling neophytes, I’d been under the impression that the wheels fully recessed into the soles of the shoes when not in use and were perhaps deployed by a wriggling of the toes or some other hidden mechanism. The wheels are in fact removable, but you need a tool to get them out, and it’s not all that simple to ditch the wheels once the shoes are on your feet.

The upshot is that if you want to go out heeling, you’ve got to commit to having the wheels in, and walking with wheels is not easy at first and never very comfortable. Kids don’t seem to be bothered by this, but I swear my Heelys were starting to give me shin splints. I had thought that Heelys would be as well-suited to an afternoon constitutional as they are to an afternoon of can-openers and toe jams. Instead, even if you’re just walking across the street to your favorite heeling spot, you have to be sure to come down on the ball of your foot with each step, lest you accidentally engage the wheel and go flying, as if slipping on some invisible banana peel. My biggest wipeout to date happened while walking, not heeling. I was on my way home from a field test, talking on the phone, when one of my wheels caught a little too much pavement, I launched into an inadvertent grand jeté and came down hard on my coccyx. It took a few minutes, but I eventually found my phone in a nearby shrub.

Compared with walking in Heelys, heeling is pretty simple, once you get the hang of it. You push off with one leg, put the other forward and lean back on your heels. Roll and repeat. It takes a little while to find your balance, but when you do, it’s not long before you’re gliding along with the distinct, nonchalant air of a kid in Heelys: Yeah, I’ve got wheels in my shoes—what of it?

I tested my Heelys in a variety of environments. I heeled the paths of Central Park. I heeled to work one day, stepping deliberately to avoid killing myself on the subway stairs or rolling in front of an oncoming F train. I cruised around my neighborhood in Brooklyn, noticing for the first time how varied its sidewalks are: Some are smooth and flat, others so beveled as to stymie even the most vigorous attempt to heel. I took in “The Shapes of Space” show at the Guggenheim, attracting quizzical looks but surprisingly no reprimands from the docents as I spiraled my way from the sixth floor down to the lobby. But by far my favorite venue for heeling was Whole Foods. The concrete floors in the Columbus Circle store are well-buffed and slightly veneered, making them slick but not slippery.  

My fondness for the Whole Foods experience, though, isn’t purely a function of its fast surfaces. Unlike their ancestors the rollerblade and the skateboard, Heelys aren’t really designed to get you from one place to another—unless the trip is all downhill, heeling isn’t any quicker or easier than walking—or even really for doing tricks. The primary function of Heelys, as I see it, is to make boring activities a little bit less boring.

YouTube, unsurprisingly, has a vast collection of heeling videos, and cycling through them, you can’t help but notice how many are shot at the mall—or at Wal-Mart, K-Mart, and Target. Watching this footage, I was reminded of all the downtime of childhood, of being dragged along to the supermarket or the department store and left to entertain myself while my parents ran their errands. Those errands would have been a lot more fun if I’d been cutting up some linoleum in my Heelys.

I’m not the only grownup who has discovered the joys of heeling in Whole Foods, but I don’t think an adult Heely fad is in the offing. Heelys have neither the sports applications of rollerblades nor the countercultural vibe of skateboards (though this might change if schools keep banning them), which might grant them broad appeal among those of us old enough to have a real set of wheels. Then again, these things can be hard to predict. The greatest use of Heelys that I’ve come across paired them with the bizarre practice of “ghost riding the whip”—a pastime of Bay-area hip-hoppers wherein you get out of your car while it’s still moving and dance on and around it. In this mesmerizing video, a guy heels circles around his pick-up as it rolls, unmanned, through a darkened parking lot. If this catches on, more grownups may yet buy Heelys. You can’t ghost ride the whip if you don’t have a driver’s license.