Committee on Environment, Geography and Urbanization

Division of Social Sciences, The University of Chicago

portrait of Stella Bennett

Most people will never end up at Skyscraper Heels. I, however, have been twice. The first time I showed up at the small custom high-heel shop on a quiet commercial street in Chicago’s Roscoe Village, it was closed, despite the hours on the website. There were two pieces of paper taped to the door instead: “Back Thurs 8-11-22 at 12p” and “Call first. I’m out of town a lot.” The next weekend I did call ahead and told the sole employee, Gary, my sob story. “My feet are too small for women’s shoes but too wide for children’s shoes,” I explained. I usually end up buying kid’s shoes that I eventually manage to break in or I shuffle around in women’s shoes with too much room in the toe. Did he have heels in a women’s size five? Yeah, he said, not many, but he could dig some up. And yes, they were open.

Skyscraper Heels, Chicago’s only destination for custom high heels, has a formidable, intriguing website. The font is comic sans. The color is purple. Glitter is everywhere. It is not fit to be viewed on a mobile device. They advertise “hard to find sizes for everyone.” Also: “CORSET FITTINGS ARE BY APPOINTMENT ONLY.” The website, and the store itself, seem to be frozen in time at least 20 years ago. In retrospect, the fact that I trusted the website hours and took an hour-long journey to Roscoe Village without ever calling ahead seems like punishment for my hubris as a digital native. My parents always call ahead. I almost never did, but now I’ve learned my lesson.

I spent three or four hours in Skyscraper Heels (the second time, when it was open), wavering endlessly between a pair of black synthetic leather heels and a black-and-white lace-up number meant to make my feet look like they were wearing little tuxedos. I sunk into the store’s fading floral couch, nestled in the middle of a dozen dusty shoe boxes which Gary had unearthed from the basement or back room (it was unclear which; all I know was he disappeared behind a wall and came back again). I was desperate to finally find the solution to my shoe woes, but Gary, a seventy-nine-year-old, slightly hunched man with thinning gray hair, small glasses, and colorful suspenders, seemed strangely unbothered by whether I bought anything. He kept handing me boxes and making pessimistic comments about their contents: “These will probably be too narrow,” “I hesitate to sell these because the straps are falling off,” “these will probably pinch.” But he kept bringing them out, and I kept trying them on, hoping for a goldilocks pair.

My indecision allowed me plenty of time to observe the other customers. At 21, I was the youngest in the store that day. The others were three middle-aged pairs—a husband accompanying his wife on a corset-buying mission, two friends who had driven all the way from Indiana to find black leather platform heels in a men’s 14, and another pair who stopped in briefly and left, possibly crowded out by the rest of us taking up space in the one-room store. Skyscraper Heels is about the size of your average living room, with a window display in front, an open area with a couch and display table on the left half of the room, and a cash register and desk in the back right corner. Every other surface is taken up by shoes: dozens of shoes sitting on shelves on the wall, hung on metal rods, stacked in the window, lining a rack by the door, and stacked in boxes around the ancient couch. They are red, black, white, and pink. They are polka-dotted and rhinestoned. Some are real leather, others synthetic, from kitten heels to thigh-highs. The dusty shoeboxes piled in cairns throughout the room don’t help the claustrophobic atmosphere. Gary implied he hadn’t cleaned up because he hadn’t had the time, but then again, he told me when I arrived around noon that I was the first person to come into the store that day.

Cramped as we were, we couldn’t help but acknowledge each other (something that would never happen in a DSW). Soon, I was getting feedback on which pair of heels everyone preferred. I marveled at the size 14 platforms, and everyone else marveled at my size 5s. The corset-seeking woman, a redhead whom Gary was lacing up into various contraptions, said they looked like doll’s shoes. Gary sounded dismayed but unsurprised as the man trying on black latex platforms failed to zip the boot around his calves. “This happens a lot with men’s legs,” he lamented. It seemed we’d all traveled from inconvenient locations to get to Skyscraper, and we’d all come with a specific need in mind, looking for an expert to help us. The corset-buyers and platform-purchasers passed no judgment on each other. The only judgment passed was Gary warning me about the four-inch black heels I was eyeing, which had little silver locks on the ankle straps. “Those are kinky shoes,” he informed me. “Be careful what crowd you hang out with in those, they might get the wrong idea.” I asked what made them kinky shoes. He pointed to the lock charms. “It’s so you can’t get out,” he said, and left it at that. I bought them anyway—for the pleasant jingling sound the locks make when I walk.

In his former lives, Gary has been a drag queen, a moving company founder, and spent some time “prospecting” out in the southwest (whether for business opportunities or for gold is unclear from his telling). He got into the shoe business in the early 1990s after a friend of his established a plus-size lingerie store on Lincoln Avenue (which then moved to West Belmont Avenue). Gary started selling shoes on consignment in the lingerie store and met with enough success to consider opening his own store, which he did in 1998, in a storefront across from his friend on W Belmont, a street known for its antique stores. The rent on this stretch of W Belmont is cheap and has been for the nearly twenty-five years Skyscraper has been there, only the first ten of which were truly profitable, Gary explained, to my surprise. “As long as I can make rent I’m fine,” he added.

I came to Skyscraper because online shopping doesn’t often work for people who fall outside standard sizes. I’m convinced online shopping doesn’t work for most people, but since Zappos started offering free returns in 1999, the world of online shopping has become cheap enough and convenient enough to be worth engaging with. Online shopping and/or curbside pickup is incredibly convenient for companies, which can then pay fewer employees because in-person customer service becomes redundant. Of course, for people who are housebound for one reason or another, ordering online is non-negotiable. But when I can, I greatly prefer in-store shopping. Finding the right salesperson for my conundrums can make or break a shopping experience. Talking to Gary felt like talking to a consultant, someone who is invested in solving a problem with me, rather than just pointing me to the right section.

I was raised to have a great deal of curiosity and respect for craftspeople, small business owners, and little out-of-the-way stores. Most of my grandparents grew up on farms, and my grandfather ran a beekeeping operation in Virginia in the late 1960s and early 70s, then became a hearing-aid salesman. Farther back in the family tree, you’ll find plumbers and bakers. You can’t travel with my family without frequent stops at roadside stands or boutiques and a barrage of questions: “Where does this propolis honey come from?” “How long is the season for peas out here?” “How was this leather made?” We were people who made and sold things, and now that we are not anymore, we buy things from people who make and sell things.

Though he knows his way around a shoe, Gary doesn’t make his wares himself. Instead, he has corset and shoe contacts to whom he can call in custom orders (a women’s 12 of the latex platform boots but in red; a corset made with a special fabric). Gary’s role is intermediary between supplier and customer as well as salesman for the models that can be bought right off the shelf—he orders what he suspects will sell and then calls in more specific requests as needed. I listened intently as Gary explained how the heels are constructed, with which materials and which glues. Some of them desperately need repairs, but the shoemakers he used to send orders or repairs to out in California have shrunk in number, retired, or closed. Shoemakers and shoe repairmen are a shrinking industry, largely due to trends towards casual athletic wear as opposed to the traditional office attire that might demand Oxfords. Shoemakers can’t necessarily repair sneakers, which are designed to be thrown out and bought again when they wear down. A lack of shoemaker contacts means many of the older heels at Skyscraper may come apart without anyone to reglue them, making them impossible to sell responsibly. Despite this declining traffic, Gary didn’t overcharge me for the black heels—in fact, he shaved off twenty dollars because one of the straps had visible wear, and he threw in the lock charms for three dollars each. He announced everything that was structurally wrong with the shoes, put them in a box, and wished me well. I walked out wondering if the shoes really did fit or if I imagined that they did because I couldn’t spend three hours going through dozens of disintegrating boxes of hand-glued heels and leave without giving him anything in return.

Skyscraper’s customers are people who can’t find what they’re looking for at a typical shoe boutique. Gary told me their customer base is “crossdressers, drag queens, and transsexuals” (the previous generation’s “transgender”). There’s a framed photo of Gary himself in drag hanging above the register. The store’s location right in the middle of Roscoe Village attracts a suburban element, too. While it’s not a true suburb, still within the bounds of Chicago’s urban sprawl, Roscoe Village is extremely residential. The North Side neighborhood is one of the quietest places I’ve been in Chicago, even on weekends. A painted bridge on Ravenswood Road reads “Welcome to Roscoe Village” on one side and “The Village Within the City” on the other. Roscoe Village presents itself as a kind of quaint, tight-knit refuge from the bustling downtown, though you wouldn’t guess this from Skyscraper Heels’s name or the city skyline on its awning. During summer weekends, some of Roscoe Village’s wide streets are cordoned off for block parties or outdoor restaurant seating. Everything seems a little slower here. Young families stroll around, cyclists pass leisurely with Bluetooth speakers playing from their baskets, and the neighborhood’s “L” station is well-maintained but nearly empty. Gary mentioned that “housewives” will often come in looking to try on a pair of thigh-highs “to spice up their sex life,” only to wobble when they try to walk around. The customers from Indiana came to Skyscraper from the real suburbs to find men’s platforms in the more liberal Chicago, which has such options, but having traveled from my apartment on the South Side through the heart of downtown all the way to the North Side, Roscoe Village felt like the suburbs to me. Given its name, Skyscraper might be more at home among the drag clubs close to downtown, but the rent would be unforgiving. Still, it acts as an exciting urban enclave of one in sleepy Roscoe Village, attracting high heel tourists, whether men with a hobby or Gary’s “housewives.” I can’t help but picture him bemusedly looking on while a prim woman who wouldn’t set foot inside a go-go bar tries to zip up patent leather boots and almost topples into the piles of boxes that are always on the verge of being reshelved. But business is business: housewives will never be turned away. Of his customers, Gary said, “We need ‘em all.”

If anything, Gary seems eager to introduce everyone to a taste of the sensual, even if they are uninitiated with the world of fishnets and stilettos. At some point in every customer interaction (at least with women, in my observation), he’ll tell you he wants you to try something on, scamper delightedly into the back, and return with a $200 black silk corset. He insists that everyone should try it, just to see. By the time he pulled this song-and-dance on me, I shrugged and stood as still as possible while he deftly laced up the bodice. I sent pictures to my friends, silently gawking at the way I had suddenly been pinched into a dramatic hourglass. “Look what it does for the hips!” Gary raved. “Your posture!”

Under different circumstances, this whole routine might make me uncomfortable, but it was clear that the corset fitting was not about me or my waist in particular. Everyone gets corseted, and Gary is delighted in exactly the same way each time. At no point do you ever feel like you’re wasting his time. It’s clear he would rather be doing nothing else; he has something for everyone, time for everyone, and compliments for everyone. “See how the heels change your walk?” “Look what they do for the legs!” I rolled my eyes internally at these phrases straight out of an 80s makeover movie, but I took them less as an attempt to make me sexy and more as an attempt to get me excited about the ways I could transform myself. Like one might believe in the power of positive thinking or an apple a day, Gary believes in the power of shoes. Despite his brutal honesty about the disrepair of his stock, if you find a pair that works, Gary will make it known. “They change your walk!” he’ll cry with the faith of a magician. “They make your calves look amazing!” Gary knows what he can adjust for (“That platform is too long, I’ll get another from the back,” “I have a smaller heel in purple”) and what is a lost cause (“We only have that slingback in brown. The guy went out of business”). The shoes will serve you well for years, at least the ones with glue still intact. The corsets will too, until you stretch them out. This is the joy of investing in products made and sold with intention, made and sold to last. It would be easier to buy something with a few clicks and a tracking link, yes, but I can go back to Skyscraper Heels when my ankle straps wear out and buy new ones. I can go back anytime I need a shoe expert, the opinion of three to four strangers, or simply a beautiful thing I can hold in my hands and know where it came from.

portrait of Stella Bennett
portrait of Stella Bennett