few months after graduating from college, I interviewed to be an assistant in the events department at a magazine. The whole experience felt surreal, and getting offered the job seemed altogether unlikely. But a couple of days later, on a windy day in mid-April, my soon-to-be boss called and asked me two questions: “Do you want the job? And can you start tonight?”
I answered yes to both. She told me to be in front of the New York State Supreme Court building at 6 p.m., where they were throwing a party for the Tribeca Film Festival. I’d be helping check guests in at the door — my first of many turns as a glorified bouncer — and since I’d be standing outside for a few hours, she instructed me to “dress warmly,” which is precisely when I panicked.
I stared into my closet and tried to draw a mental venn diagram of “clothes I own that are warm” and “clothes that a public-facing Condé Nast staffer would wear to a party.” I’d just spent four years at a liberal arts college in Vermont, so needless to say, the two circles didn’t exactly intersect. I cobbled together a makeshift black suit out of a tuxedo jacket and trousers from two different brands, wore them over a black crewneck sweater, added a set of heavy, dangling pearl and pastel earrings, and because I didn’t own any practical black heels (and in my 23-year-old mind, all Condé Nast staffers must always wear heels), shoved my feet into a pair of navy blue Helmut Lang calf-hair stilettos that I had recently impulse-purchased with a Barneys gift card.
It was an objectively bad outfit. It was neither warm nor chic. It was also the beginning of an era of fear-based dressing. My early days at 4 Times Square involved a succession of outfits that were, for the most part, informed by an entirely self-imposed idea of what I thought this new, glamorous phase of adulthood was supposed to look like. I laugh-slash-cringe now thinking of some of my attempts to fit into that imaginary mold. I tottered back and forth to the mailroom in turquoise suede single-sole pumps. I wore tailored blazers and pleated midi skirts. I maintained a collection of silky, demurely colored, office-appropriate work tops. I remember feeling very much like a grownup the day I bought a pair of black and nude stacked-heel Lanvin sandals.
In a 1973 Esquire column about her hero, Dorothy Parker, Nora Ephron wrote that the reality of who she was was almost besides the point: “The point is the legend. I grew up on it and coveted it desperately.” Like Ephron, I grew up wanting to be someone who didn’t really exist. Or, to be totally honest, I wanted to have and wear the kind of clothes that would prove I had become that sort of someone: the right shoes, the elegant bag, the perfectly tailored pants.
The version of an editor I thought I wanted to become might have been real in another era, but I’m pretty sure it stopped existing long before I frantically threw together that missguided black “suit.” Four years went by quickly. I moved out of events, then onto the editorial team at another magazine. By the time I had worn out the soles of a lot of heels, I was close enough to the ideal that had been propelling me forward to realize it was a mirage. One day, I looked around and realized I didn’t want any of it anymore. And then I quit.
Now I work from the apartment I live in alone or a library where I post up at a desk hidden in a back corner of a rarely-frequented part of the stacks. Aside from passing nods with other library regulars (old men in cardigans teaching themselves Italian, exhausted-looking med students studying for exams), I rarely experience significant human interaction before 7 p.m. on weekdays. For the first time in my life, I’m putting together day-to-day outfits without an audience in mind.
The concept of “dressing for yourself” takes on a whole new meaning when you are, quite literally, dressing only for yourself. Do I occasionally spend the entire day in leggings and a sweatshirt? Sure. But most of the time, I don’t. Clothes started feeling way more fun again when the word “should” stopped being a part of the equation. I find myself reaching for things I’ve owned for years, hitting “add to cart” on pieces that just make me smile, layering on accessories that have happy stories attached to them that only I know.
The style I’ve landed on looks like some combination of “dirtbag WASP” and “artsy grandmother.” I wear vintage button-front dresses with beat up Supergas, embroidered scarves and patterned oversize button-downs, my ex-boyfriend’s red cable knit sweater with burn holes on the cuffs. I rotate through a pile of Organic John Patrick knits (soft as hell, perfectly boxy without being stiff, colors that make sense pretty much year-round) and multiple colors of the same Frame jeans (Le Crop Mini Boot, which I cropped even further with a pair of kitchen scissors because I’m 5’3). If I’m not in sneakers, I’m in loafers: Leopard print Dieppa Restrepos, a scuffed up silver pair from Zara, or embroidered velvet Stubbs & Woottons I picked up at a consignment store in Florida. The jewelry I wear every day feels almost totemic. I pile on beads in mismatched colors, my mom’s old charm necklaces, rings I bought on trips abroad or that remind me of my best friends.
It took me a while to separate my idea of what I had hoped adulthood would be from my actual experience of it. I focused for so long on what it was supposed to look like that I barely experienced what it felt like. It’s been interesting to apply this distinction to other parts of my life: How many of the decisions I make are based on external factors, and how many are based on self-imposed rules? How much of what I want is based on something I decided I wanted before I had all the information? How often do I ignore what I’m feeling because it would contradict the image I’ve created of myself?
When I stopped thinking of clothes as battle armor, I started thinking of them more as decoration for my own amusement. I still have those demure silky tops, but I wear them unbuttoned, with ten necklaces and the tails tied in a knot. I’ll wear my turquoise pumps, but only with a black-tie gown. It took years of mistakes, style-related and otherwise, to even begin to figure out what I really want out of my adult life. Chances are that what I want will change again in the next four years, but I think I’m getting closer to it, and feeling like myself has made looking like myself a lot easier. To entirely misuse the Marie Kondo ethos: If it sparks joy, I put it on.
Photos provided by Andrea Whittle.