To clarify: I'm not an aesthetic masochist. Personally, I believe my collection of sandals, sneakers, lace-ups, and boots are beautiful. Ugliness — like beauty — is in the eye of the beholder, and while I wouldn't go as far as stating that Louboutins and Jimmy Choos are fug, I would say that they aren't challenging in a way that turns me out. Miuccia Prada recently said some really awesome things to that tune in an interview with T: "Ugly is attractive, ugly is exciting. The investigation of ugliness is, to me, more interesting than the bourgeois idea of beauty." Oh, Miuccia! Give me a lug sole Prada sandal with thick straps over a delicate Brian Atwood pump any day!
My relationship with ugly shoes, however, hasn't always been this positive. As a child of immigrant parents in the Midwest, fashion wasn't necessarily at the top of the list when it came to how to divvy up the monthly budget. No LA Lights or glitter-red Dorothy slippers for me; I grew up on a steady supply of hand-me-down boys' sneakers that were always a little too big, to ensure that they'd fit my always-growing feet for a little bit longer. As someone who already stuck out enough being the only Asian kid in a predominantly white community, each time I felt like I had to hide my Ninja Turtle kicks around the other girls' Rainbow Brite ones made me feel more like the weirdo who didn't quite belong.
In middle school, I was finally able to pick out my own clothes, and went straight for what I thought was the best imitation of what I saw in the fashion magazines I saved up to subscribe to. I bought candy-colored high heels and patent leather clogs, platforms sneakers and kitten heel flip-flops. Though it's definitely not the case now (kitten-heel flip-flops, really?), then it seemed like I was buying the most beautiful shoes I could afford. Playing around with personalities — faking it 'til you make it, if you will — is an important activity for any young person to engage in, and it was through dressing like a fashion editor (or at least, what I thought a fashion editor dressed like), that I felt confident enough to pursue that world, even though I'd never owned anything with a designer label.
After college, I swapped those flip-flops for gladiator sandals, those platform sneakers for wedge boots, and hobbled my way to New York City. Pretty soon, I was a bona fide fashion editor, made enough money to actually afford real deals, and found myself the victim of one too many rolled ankles. I spent a month in flats and discovered that I loved the feeling that I could walk anywhere, anytime. Eventually, I realized the power of standing tall in a flatform (instead of wobbling tall in stilettos). That I loved how a weird shoe could make a too-cutesy sundress suddenly look just right. That I had a minor obsession with white soles with oversized treads. I was hooked.
The great thing about ugly shoes is that they're aesthetically subversive in the comfiest way possible. Who says feet look better when they look smaller? Or that it's so important to try and create a long leg line? I think my feet and my legs do fine on their own without the aid or impediment of a shoe. Plus, ugly shoes aren't obvious. While people may expect to see a college student coming out of Intro to Anthropology in a pair of Birkenstocks or a fashion editor coming out of Lincoln Center in a pair of towering Alaïas, seeing a fashion editor in a Carven short suit and a pair of 'stocks is a whole lot less predictable. Being approachable, practical, and original are qualities that are important to me as a fashion person (and a person person, now that I think about it). I've never quite figured out how to do a proper bitch face or inspire true fear in a crowd, and for some reason, I think that's true of most people in the Ugly Shoe Club. What's more approachable, practical, and original than a colorful pair of Tevas?
So, how do you wear an ugly shoe? I can't really tell you, specifically, because if you're the type to really love a weird shoe, you're probably also the type to not really pay attention to other people's opinions about your fashion choices. Ugly-shoe fans are a contradiction: We're on-the-go, we're fashion-forward, we're slightly off-kilter, we're fans of nostalgia, and we hate being told what to do and how to look.
So, the next time you see a pair of five-toe shoes and point and laugh? …Actually, scratch that. Those are never okay.