A few months ago, I was flicking through a rack of vintage capes at Chelsea’s West 25th Street Market in NYC when my friend broke my heart. “You know, it might be time to retire those boots,” he said, eyes cast down toward my feet. His expression was a careful blend of dismay and contempt with a pinch of pity—the type of concern reserved for the unreasonable and the maybe beyond help. (He looked like he was confronting a hermit perched atop a mountain of American Girl dolls.) “They’ve … seen better days,” he added.
“Oh, but they’re perfectly worn-in!” I said, laughing merrily to downplay my distress. It made me sound more distressed. I tried another tack, pleading: “Every time I wear them, someone stops me on the street to say, ‘Nice boots!’ ”
My studded motorcycle boots, you see, are beloved. The holes in the toes are patched with electrical tape, which I believe denotes character. But my friend was right; they’d seen better days—earlier days. Almost-a-decade-earlier days. But giving up on them felt like defeat—one more concession on the altar of adulthood, like health insurance co-pays, going to bed at a reasonable hour and wearing beige by choice. My boots weren’t just footwear—they were me at 18, betraying my New England boarding school roots and stomping all over New York. But that was then. As a fashion and culture writer midway through her 20s, what in the hell do I wear for my life now?
Aging is great and awful for any variety of reasons. There’s the famous line from The Sun Also Rises about going bankrupt “two ways, gradually and then suddenly.” Growing up is like that, not least when it comes to what you wear and looking “pulled together.” One day you try your very hardest to look like you just fell out of bed and don’t give a damn, and then the next you do give a damn, hugely, but you’ve kind of forgotten how. A quick visual survey of my peers led to the realization that dressing with any personality seemed to imply cultivating the impression you didn’t need a job and didn’t care what anybody thought. Or you swung the other way, embracing “adult” attire that felt depressing: individuality-stripping pencil skirts and stretch twill and whatever slacks are.
I liked my job, and I wanted to be good at it. So purposely underdressing wasn’t doing me any favors. As the always impeccably attired PR legend Peggy Siegal once told me: If you dress like the help, they’re gonna treat you like the help. Dress like the chairman of the board. (In case you missed it, she’s saying that your artfully shredded tank top isn’t exactly telegraphing your serious work ethic.)
So I considered that old trope “dress for success”—and the merits of a uniform. As Diane von Furstenberg wrote in her 1977 Book of Beauty, “One of the most important things about fashion is to dress as well as you can, look as attractive as you can, and at the same time be comfortable with yourself. Be easy about your clothes, forget about them.” You know what lets you do that? A uniform.
As for what happened next, well, I started playing around with what mine would be. White button-downs became my catnip, especially paired with sleek trousers (black, gray, printed!) or perfectly fitted Acne blue jeans. Good blazers, I came to realize, are magic, and camel, for the record, is decidedly not beige. Not only was I notably shocked by how great-looking a pencil skirt is, I can proudly now confess to you my love for black cardigans, cashmere turtlenecks and expansive loops of scarves.
I avoid clothes that convey “slouch,” opting instead for those that fit perfectly—or as close as I can generally manage. Tailoring looks expensive, even when it’s not, and it gives off a sophisticated vibe. I realized the deft and understated power of the single-sole pump. (Both literally and figuratively elevating!) I also invested in elegant riding boots, and while I will admit to purchasing new combat boots, they’re Chanel. It hopefully goes without saying that there are no holes.
I did the work: I built up staples, I pared down my closet—adios, “boyfriend” anything, whim purchases I never wear, anything overtly branded or too trend-tied. I donated so much that I am hoping to have made a significant karmic dent. Calling it a style evolution seems severe (I haven’t yet grown gills … yet), but there has been significant progress: I dress now like I have my life together, and as a result, I feel that way too.
And I still have those studded boots, even if I don’t wear them. Maybe “me” at 70 will get a motorcycle … and a genius cobbler for some much-needed repairs. I don’t feel defeated by the real world and its associated requirements. Dressing like an adult doesn’t have to be complicated, and it certainly doesn’t have to be boring: As the divine Diana Vreeland said, “I hope to God I die in a town with a good tailor, a good shoemaker and perhaps someone who’s interested in a little quelque chose d’autre.”