When Did I Become a Fashion Robot?

For years I was the girl with the out-there look: a pre-Leandra man repeller who proudly delighted in her own sartorial weirdness. And then, something happened: I became basic. No, I became boring.

Illustration: Jenny Williams; Photo: Joslyn Blair

There's an old picture of myself of which I'm very fond. In it, I am a towheaded seven year old, standing about 3'5" high, and wearing, I kid you not, my brother's plaid boxers, a leotard I sheared into a crop top that hits just below my ribcage, and sloppily laced, red, high top Converse Chucks. I am at school. I look awesome.

My history with out-there personal styling is a long and colorful one. Aside from my affinity for wearing boxers as pants, there was the era of the Rhinestone Cowgirl As Envisioned by the von Trapp Family (see below), my DIY dELiA*s decade, and the scarf-as-bandeau college years (a time during which I also became a large proponent of the "backlace," a necklace rotated backward so that it settled neatly between the spaghetti straps of my C&C tank top). Not to mention the fact that I designed my own Bat Mitzvah dress out of a swath of midnight blue velvet, a yard of silver sequins, and some voile piping.

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But somewhere along the line, it seems, I have lost my mix master mojo. Perhaps it's the intimidation factor of working at a fashion juggernaut like Hearst, which, in addition to ELLE, houses editors from Marie Claire, Harper's Bazaar, and Cosmopolitan among other stylish titles. Every day when I step into the mirror-lined elevators at my place of work, I pray for a Tommy Ton-esque ragamuffin reflection—you know, layers that flap casually in the wind, JBF bedhead, boots that don't reveal the telltale ankle scuffs of pronated knees—but am instead met with some version of the same: jacket, black; jeans, skinny; hair, sorta limp but pretty much decent; purse, black, large, and heavy. Gone from my ensemble, it seems, are the unexpected dashes of personality: a bright yellow Hermès 'Twilly' scarf I used to tie around my wrist for fun; the unabashed tangle of H&M necklaces I was fond of braiding into a rope; my penchant for layering party dresses over an old beat up Calvin Klein T-shirt for daytime fun. Where, oh where, did my panache go?

More than a fear of fashion failure, the dissolution of my daring might have something to do with our current entertainment idols. Gone are the days of Clarissa, Blossom, Punky B., and Patricia Field-invented magpies such as Carrie Bradshaw (Sex and the City), Betty Suarez (Ugly Betty), and post-Runway makeover Andy Sachs (The Devil Wears Prada). Instead we're presented with no bullshit power babes like Olivia Pope (Scandal), Clare Underwood (House of Cards), and Selina Meyer (Veep). I truly doubt that Alicia Florrick ever wasted her time making a faux fur stole out of a bathmat. (True story. Deal with it.)

Cowboy von Trapp lewk; tutu-over-sweats swag; Bat Mitzvah bombshell. All illustrations by Jenny Williams

Thanks to a lethal combination of both external and internal pressures, I became convinced that flourishes and pops of color were for the weak-minded. When I shop, I began to ask myself a series of questions: 'Would [ELLE.com deputy editor] Ruthie Friedlander buy this?' (Ruthie has a knack for picking up versatile basics, while the idea of actually buying a black cashmere turtleneck all but depresses me); 'Will this go with a bunch of things I already own or will it be the catalyst for additional purchases?' And, my personal favorite, 'Will this make getting dressed easier or more difficult?' I can't tell you how many items have slipped under the radar—the feathered vest, the balloon-like silk pants, a handful of capes—before I institutionalized that last edict. And yet, for all of my carefulness and professional-level curating, I rarely knock an outfit out of the park these days.

Could I have psyched myself out of having personal style?

"The amount of our time and energy that we can—or are willing to—put into creativity and self expression, sartorial or otherwise, seems to diminish as we get older," says Jenny Williams, whose blog, What My Daughter Wore, was recognized byTime magazine as one of the best blogs of 2013, and whose book of the same name went on sale yesterday. The premise of the site is cleverly simple: Williams, a self-professed "Brooklyn Mom" draws pictures of the whimsical, un-self conscious ensembles her school-age daughter and friends put together. (She also drew the images in this story from actual photographs from my own childhood. While they are not the most extreme examples of what I've actually worn, I hope they serve their purpose.)

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"I think self consciousness and peer pressure definitely come into it," she continues, and my mind immediately flashes back to that night, a few years after college, when I wore a men's short-sleeve button down, drop-crotch pants, and combat boots to meet some friends at The Frying Pan. No sooner had I arrived than I over heard a friend telling a group of boys, "She doesn't always dress like that." They laughed, and so I did too. This, I now realize, was the first of many incidents that subconsciously hedged in my sartorial creativity. Over the next several years, I began to more carefully consider the environment I would be in and how my styling choices would be perceived. 'Better safe than sorry' somehow became my unlikely guiding principle. "If you're an adult, and a sense of freedom and fun is something that you want to recapture, how you dress is an easy and low-risk way to work some of that back into your life," Williams assures me. "Wear a bright pink hat instead of a black one. You can always take a hat off if you feel like you look ridiculous in it."

I think the girl who invented the tutu-over-sweatpants look can handle a pink hat, amirite?