Is There a Place for Uptown Fashion in 2022?

In 2009, I moved to an apartment on New York’s Upper East Side. Twenty-two, fresh out of college, and jobless, my options for housing were limited. An old friend and I moved to the city from the Midwest the same week with no money and no backup plan, and by dint of our sheer delusions convinced a management company to rent us their worst one-bedroom apartment. Located beneath the Queensboro Bridge, the apartment would prove a semi-harrowing place to live. Its heat and hot water were erratic, its window faced a brick wall, and the fact that one of our beds was in the living room turned it into something of an anti-bachelorette pad.

But that first chaotic fall in the city, I would come to discover my new neighborhood itself operated as something of a balm. The Upper East Side was everything my own life was not: orderly, luxurious, solid, and grand. Deep down, I was afraid—that my gambit to move to work at a magazine in New York without a safety net would fail, and I would have to slink home to my parents’ basement in Missouri with my tail between my legs. But when I walked a few blocks west from our apartment, I found myself in a world of Beaux Arts townhomes and bona fide ballgowns. And these atmospherics made failing feel impossible. They were the polar opposite of fear, or falling asleep next to your kitchen sink. When I slipped on a tiny brocade minidress and silk headband of my own, this softness and luxury functioned as both armor and escape. My clothes, like my neighborhood, were another form of slipping into the future perfect; totemic and absurd in equal measure hanging in our apartment’s one shared closet. What I meant when I wore them was that I wanted a life that was more than scraping by. And uptown clothes let me pretend for a little while, even to myself.

In the aughts, this had the added benefit of making me fashionable. Even distinctly downtown designers—from Marc Jacobs to Anna Sui—seemed to have been inspired by the original uptown bad girl (and W alum) Blair Waldorf. Their designs, along with those from mainstay uptown brands like Oscar de la Renta and Carolina Herrera, embraced the silks, jewels, and out-and-out prep that have defined the uptown aesthetic for generations. It was a time when Jason Wu dressed Michelle Obama in chiffon ballgowns and peplum reigned supreme.

In the years since, my life has changed, and fashion has changed along with it. As my day-to-day became more stable and secure, I stopped needing to use uptown clothing as a psychological prophylactic, and started appreciating it on its own terms. While my style didn’t change, much of the fashion worlds did, as the uptown aesthetic of the aughts gave way to sportswear, street style peacockery, and the matte, monochrome ath-leisure favored by the Kardashian sisters; luxury democratized, via Calabasas and the infinite scroll.

As a committed leftist, this democratization was everything I believed in. High fashion had been for centuries largely the dominion of the thin, white, and to-the-manor-born, and it was difficult to reconcile these oppressive demographics with my own ethics. Now, high fashion is infinitely more diverse. This is not to say that it’s perfect, or that the work is anywhere near done. But the ethos of high fashion now is one of almost infinite permutations of beauty. Hijabs walk runways, gender-fluid collections are the norm, and ad campaigns, editorial spreads, and even collections themselves are notably more multicultural than they were even a decade ago. (To wit: Ralph Lauren’s recent capsule collection inspired by historically Black colleges and universities, which the brand said was born out of a desire to share “a more complete and authentic portrait of American style and the American dream.”)

But can there be modernity in a tweed skirt set? Some of the most exciting uptown-inflected designers working in American fashion today certainly think so. “I think that with social media, styles have really merged and remixed into a new genre,” says Mark Cross’s new creative director, Rebeca Mendoza. “What’s fun about fashion, and what’s fun about styling, is bringing cultures together and making it your own. For example, wearing a really bold sneaker and having it mixed with a very beautiful and classic vintage dress.” Markarian designer Alexandra O’Neill—who has dressed no less than First Lady Jill Biden—agrees. “A friend wore one of our mini dresses out this week with a pair of sneakers,” she told me, “and it looked so good.”

Indeed, perhaps what is antiquated is the idea of geographic silos at all. Mendoza says that she and her designers think about a woman grabbing her Mark Cross bag for a night at the opera before heading downtown to a friend’s apartment for a late-night party. “People are multifaceted,” she said. And though O’Neill’s designs looked stunning amid all the pomp and formality of Inauguration Day, they would work beautifully at a backyard dinner party in Brooklyn, insouciantly luxurious and feminine spangling amid artists and grass. They are joyful clothes, made for getting into good trouble, rather than lunching as a verb.

So too does the classical nature of so much uptown fashion cut against the nihilism that underpins more of-the-moment aesthetics like indie sleaze. Nihilism is an understandable response to the world today, with its ripped jeans and greasy roots serving as visual manifestations of internal anomie and alienation. Uptown fashion, on the other hand, is the dominion of the bleedingly sincere. To put on an Oscar de la Renta minidress is to say that you haven’t given up yet. That you hope—like me, sleeping next to my kitchen sink—brighter days are on the horizon.

That kind of hope can break your heart. But it can also serve as a form of resistance against the relentless pace of late capitalism; venerating slowness, softness, and beauty for its own sake, while insisting that moments have meaning and matter. “Whatever your style, I think it’s important to put effort into putting yourself together,” O’Neill told me. “It’s a sign of respect for whatever you’re going into and a sign of appreciation. It shows that you tried and that you are respecting the time that you’re going to have with someone, or the experience you’re going to have.” Both Mendoza and Danarys New York designer Natasha Das also pointed to the sustainability factor of luxury pieces built to last. “Uptown style stays true to classic silhouettes and timeless beauty, instead of trends that can change dramatically over a short period of time,” Das told me.

Classically feminine style can also cut against the false binary still so often posed between the female and the serious. “I think historically people didn’t want to dress in a feminine way because it wouldn’t be taken seriously,” O’Neill said. “I like to play with that in my work.” And indeed, the point isn’t so much that a woman can run a boardroom, write an award-winning play, or map the human genome in a delicate lace dress. Rather, it is that in so doing, she is telegraphing a message to her spectators that she simply doesn’t care what they think. And this indifference of hers is a quality beyond seriousness: instead, it is power.

If uptown fashion has been out of style past few years, it may just be due for a comeback. Although they are better known sartorially for the Y2K cargo pant and tiny sunglass look, Gen Z’s defining philosophical perspective is that the world they’ve inherited is a dumpster fire of which they want no part. And despite their progressive politics, so much of what they want instead is adopted from the past, as the Carlyle Hotel’s freshly necessary bouncer at the decidedly old-school Bemelmans’s Bar can attest. “I think younger generations have a real depth of appreciation for something that’s long-lasting and classic,” Mendoza says.

Defiance doesn’t always come cloaked in the trappings we think it does. Luxury has for a long time been the domain of those born with privilege, or at least those who have already amassed their own wealth. But when I look back on my first fall in New York, alone and afraid and yet still somehow hopeful, stopping to stare in the windows at Carolina Herrera, I realize that I was part of a long American tradition of strivers who have done just that. From Truman Capote’s tiara-adorned Holly Golightly—a working girl if there ever was one—standing outside of Tiffany’s in the morning to Marlowe Granados’s dreamers in her hit novel Happy Hour, careening through New York on little more than comped Champagne, borrowed silk, and prayers, those to whom softness, joy, and safety mean the most are perhaps not those who have always had it. Uptown is about life in excess of survival. It is most modern when its gates are crashed by rebels and interlopers, insisting that no matter their current circumstances, life be gorgeous anyway.