Maura McAndrew
March 04, 2016 12:18 pm

Today I thought about wearing heels to work, but thought better of it. Instead I reached for my current go-to for any occasion, a pair of granny-style Ferragamo lace-up oxfords I recently purchased secondhand for $11. Throughout the day, I’ll catch a glimpse of my reflection and wonder, would this dress have looked better with the heels? and do I look short? The answers are most likely yes and definitely yes (I am short; there’s just no getting around it). But when I look down at my feet in my little granny shoes, I feel like myself, I feel at ease, and I feel just a twinge of happiness that I’m not wearing heels—I can walk the way I walk, or ride my bicycle, without too much clacking, or teetering, or awkward adjustments of movement. Particularly with vintage oxfords, I also take pleasure in their timelessness: I could be looking at the feet of a woman from nearly a century ago, and an unconventional woman at that.

Lace-up oxford shoes have reached peak popularity in the past few years, available in every style and color and seen on the feet of trendsetters like Taylor Swift and Emma Stone. Adapted from the men’s style popularized at Oxford University in the mid-1800s, oxfords have a sharp, sporty look that makes them good for work and play, day and evening. Most oxfords—even the heeled variety—are more comfortable than your typical heels, something even those who live in heels have to admit. Heels have been proven to cause foot and balance problems for life-long wearers and most of us, the older we get, tend to gravitate to “sensible” more than we might like to admit. And really, what better evidence that flats are where it’s at than high heel devotee Victoria Beckham’s recent conversion?

But while there are many varieties of sensible flat shoe, oxfords are the only style with full toe coverage, sensible laces and the ability to evoke either the schoolgirl or the schoolmarm (cute or ugly-chic). Much of their appeal for me relates to the effortlessly cool ladies from history that pioneered the oxford: the trend dates back all the way to the 1920s, when the “flapper” look challenged the conventions of “feminine” style. In addition to bobbing their hair and shortening their hemlines, some women took to wearing adapted versions of men’s lace-up shoes. Amelia Earhart, a style icon way before her time, was one of the first famous women to adopt the oxford, often sporting them with trousers and men’s flight jackets. By the 1940s, the oxford had become widely popular, thanks in part to high-profile devotees like Katharine Hepburn and Lauren Bacall, and in part to just plain practicality: women were entering the workforce, and looking for shoes that wouldn’t have them hobbling home after long days on their feet. With the 1950s came saddle shoes for schoolgirls, and the women’s oxford was here to stay, changing only slightly over the years and remaining a vintage-lover’s favorite.

My love affair with oxford shoes has been ongoing as long as I can remember. Many girls’ first style influence is their mother, and mine was always more interested in menswear-inspired looks (vest, jackets, and flat shoes) than the ultra-feminine. Though I went through the typical “pink” phase common to any child who’s spent time in the Mattel aisle, throughout elementary school I often wore vests, ties, pants with suspenders (one of those unfortunate mid-‘90s trends), and yes, the occasional oxford shoe. I learned my first lesson about practical shoes in first grade, while attending a Catholic school with a uniform: green and yellow plaid jumper, yellow Peter Pan collar blouse (how I would kill for that now), and dress or saddle shoes. Because our playground was paved blacktop and our uniform involved tights, slippery dress flats were a comedy of errors. I remember the one day I wore shiny-new patent leather shoes I fell multiple times, ripped both knees out of my tights and spent the afternoon scraped-up and embarrassed. Enter saddle shoes, love of my life. Sturdier and smarter, they made recess a little less clumsy.

After that first grade dalliance, I wouldn’t revisit saddle shoes until my early twenties (when I bought a cheap pair from the only outlet that seemed to sell them then—Payless.com—and continued to collect as they became trendy). Once I started attending regular elementary school and was allowed to wear sneakers, I didn’t need them anymore. In high school though, oxfords were back, with an emphasis on the clunky-and-chunky. I proudly wore the chunkiest of Delia’s shoes, which a teacher told me looked “orthopedic” But which I was convinced made me look like Natalie Imbruglia in the “Torn” video. And sophomore year, something possessed me to buy some honest-to-God Hush Puppies, of the exact same style worn by unfashionable stars Matthew Perry on Friends and David Spade on Just Shoot Me. They were suede, two-tone oxfords that reminded me of my childhood saddle shoes, and despite the fact that they were men’s, legit orthopedic, and I had to order them from a special catalogue at an old people’s shoe store at the mall, I cherished them. They remain in my closet still, some of the least cool and most durable shoes I own.

Which brings me to one of the most alluring things about oxford shoes—at least styles like those Hush Puppies and their trendier Delia’s brethren—which is that they border so dangerously on ugly that they feel edgier and more exciting than simply “cute”. A friend of mine in college used to wear a pair of ugly-chic Camper lace-ups that an acquaintance once compared to “an old doll’s shoes.” She took this as a compliment and he intended it as one. In a culture of chain stores and mass-produced clothing, why not dress like an “old doll”? It’s certainly more imaginative than dressing like a Kardashian. At a recent political rally I saw many women ten or more years my junior rocking this “old doll” look. They were wearing the chunky oxfords from my youth, thick-soled, sturdy and mud-brown. They paired these with socks and shorts and weird, drape-y vintage shirts I could never pull off. It made me happy to see this style back in full force, so refreshing compared to flimsy ballet flats and over-engineered athletic shoes. Though fashion has come a very long way since the 1920s, there’s still something about women’s oxfords that feels fresh and bold: that subtle rejection of pretty, that thumbing of the nose at delicate. These girls were embracing the ugly, and were all the more beautiful for it.

Since my feet stopped growing a good twenty years ago, I’ve been amassing a closet full of oxfords—those clunky ones, the multi-colored saddle shoes, the suede, the leather, the pointed toe, the vintage and the new. And whenever I go shoe shopping to select another pair, my companion will inevitably ask, “Don’t you already have shoes just like that?” But as we grow older, we define what we like. And while I’m still willing to take some fashion risks, I know that I’ll never give up my oxfords, that I’ll be wearing them into my golden years, and that they will stand the test of the next century, as they have the past one.

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