I don’t need to convince anyone that the prospect of dating has become one of the most horrific experiences ailing young people today. Personally, over the past two years of tolerating singledom, I have found that crying on the floor after midnight is one of the best ways to get over an almost-lover. (Tile and glazed ceramic are best.) I’m not sure if this particular method of self-soothing is a universal experience, but at least for the single women I know circling 30, the bathroom floor, usually while in some version of a vintage silk slip, has become a baptismal site of sorts. It is, in part, that hamster-wheel feeling of despair and disappointment that explains why we’re abandoning the apps in droves — why we feel the hair prickle on our arms every time we see a match notification on Hinge or Feeld or Bumble or any other iPhone tile that has promised (and failed to deliver) a happily ever after. But we keep swiping and preening and hoping, because what other choice do we have?
If we’re forced to succumb to the apps’ lens of the world and accept that our online image, however hysterical, does precede us, perhaps there’s a more strategic way to brace for the self-induced lobotomy that is the modern dating scene. Not to fashion ourselves more palatable for a stranger necessarily, but more deliberate: to present ourselves in a way that weeds out the unserious suitors and saves our time, energy, and bathroom soliloquies for those who really deserve them. As luck would have it, there’s a cottage industry of professionals working to solve this very problem.
So-called dating stylists offer virtual wardrobe audits, styling sessions, image consulting, or personal-shopping services, guaranteeing outfits you’ll “feel 100 percent confident in” or promising to help you “stay true to [your] personal style,” whatever that means. Others still offer “dating photography sessions” to “present yourself in an attractive and authentic way.” And, if judging off numbers alone, some of them are raking in clients: Blaine Anderson of Dating by Blaine boasts 722K followers on Instagram, where she helps “men understand women” with instructional videos on how to get a girl back to your place, texting etiquette, and “how to get a girl thinking about you nonstop.” Pushing corny gender essentialism? Sure! But these services present a mouthwatering alternative to the idea that you’re the problem. Maybe it’s not you! Maybe it’s just your utter lack of personal style. Or, your poorly angled profile photo.
A medicated single with some war stories myself, I set out to test this theory. After all, it’s somewhat comforting to imagine that there’s nothing inherently lacking about my appearance or personality but that I simply needed to reconsider myself as a product or brand, and up the marketing spend! What a relief. For image retooling, I turned to New York–based virtual stylist Coco Schiffer. While the 28-year-old doesn’t actively bill herself as a “dating stylist” per se, the vast majority of her clients claim dating is one of the main motivators for seeking out her services. Even for those partnered or married, Schiffer says the conundrum of what to wear on a date night runs so rampant among her diverse clientele (from 20-somethings to stylish, divorced grandmas), she’s begun referring to it as an “epidemic.” She’s also found that her dating advice is gobbled up on TikTok with alarming appetite: Earlier this year, she was featured in the New York Post for her “best dating hack ever,” which she calls the “follow them theory.” Rather than wait for a dating-app match to message you, Schiffer recommends following your crush on your preferred social-media platform. It’s not a particularly novel idea, but 18,000 strangers found the Instagram hack intriguing, if not helpful. “Y’all will watch each other’s shit for a couple weeks,” she said. “Eventually … they’ll reach out, they’ll respond to a story.”
Last month, Schiffer trekked up the stairs to my third-floor Bed-Stuy apartment with four body bags of clothes and a diligent intern and got to work setting up a makeshift dressing room with the precision of a Beverly Hills plastic surgeon. As I’d explained to Schiffer in a pre-consultation call, my predilection was mostly that I didn’t feel equipped to translate my sense of self into my clothes. I could articulate what I liked — the hyperfeminine glitter of Sabrina Carpenter’s corsets and body-hugging sweetheart tops with a hint of Elena Velez’s edge; the whimsy of Tyler McGillivary and the irreverence of Chicago-based PROD; vintage Vivienne Westwood and Alexander McQueen — but I lacked the wherewithal to turn that Pinterest wish list into a functioning wardrobe. Braving the office in ill-fitting denim was nerve-racking enough; trying to outfit myself for the would-be love of my life prompted a whole different level of nitpicked anxieties, reopening little cuts I thought had scabbed years ago. But while some might describe the act of closet surgery as — to paraphrase Jemima Kirke — “thinking about ourselves too much,” Schiffer finds the whole ordeal more closely affiliated with the psychology of the self than to any narcissistic goals.
“Clothing is how we attach ourselves to an identity — how we portray ourselves to the world. Because people are super judgemental when you walk in the room, based on what you’re wearing, or what’s on your face, or how your hair is styled. That’s just our culture,” she says with a sigh, a loose-fitted Sandy Liang top in hand. “So if you’re not feeling your best in your clothes, then you’re not going to be confident.”
While I’d assumed that having a stylist come to my home would be a glamorous affair, the reality was more akin to standing in front of a warped fitting-room mirror beneath fluorescent lights — more clinical procedure than in-home fashion show. That’s not to say I didn’t enjoy being surrounded by rows of semi-affordable Sam Edelman kitten heels. But to diagnose the perceived failings of your wardrobe in front of a woman who regularly sees models and influencers undressed is sort of like pulling all of the skeletons out of your closet, then having to confront those skeletons in front of a relative (but kind) stranger: mortifying, really. As I ran my hand across a clothes rack draped with Rue Sophie dresses and Dana Foley blouses, Schiffer asked me to describe what most bothered me when getting dressed for a date. I rattled off the issues, which came to me more readily than I’d like to admit: “I tend to dress younger than I am but not in a cute way”; “I have a lot of fun, colorful pieces and don’t know how to bring an element of sophistication to them”; “I don’t think I’m dressing properly for my size and gravitate toward tight-fitting clothes that make me uncomfortable.” Noticing my fidgeting, Schiffer grabs an old Charlotte Russe top with shoulder pads out of my existing closet with an appreciative coo and smiles: “This doubles as a therapy session, by the way.”
Prior to meeting Schiffer, I’d never really attributed that head-to-toe feeling of dread (sometimes disgust?) that hit me before each first date to a simple styling malfunction. But the more time we spent identifying my closet’s weak points — the lack of denim and trousers that fit my body and not the 24-year-old size I wished I still was, and missing high-quality staples to pair with my funkier vintage finds — the more that pre-date dread checked out. What we wear and the dating rituals we partake in are, in some ways, inextricable. We want our potential partners to see us down to our core with just a few seconds of visual input, but the clothes are in the way. All a potential paramour can do is intuit who we are from the few bits of information we tell them over shared plates of oysters and from the swaths of fabric we hang on our bodies. To find confidence in accurately projecting our inner selves, we also have to acknowledge how our tastes and insecurities manifest in our clothes. However materialistic that may sound, a sense of intimacy with one’s closet allows us to show the nonthreatening person sitting across from us who we really are — that is, if we know the answer.
“People genuinely overthink it. When you don’t have your own set personal style really nailed down or mapped out in your head, that’s gonna mess up everything for you, because then you’re gonna be like, ‘Okay, I’m going on the date with this new cute person, and I want to feel sexy, but I don’t know how to dress sexy,’” Schiffer said as she handed me a see-through miniskirt from influencer favorite With Jéan. “But maybe your personal style is not sexy. So, how can we convey sexiness in other ways that aren’t putting your boobs up to the sky?”
As Schiffer points out, we sometimes get stuck mentally glitching around the idea of looking “attractive,” when the better question is: attractive to whom? There’s that image of a slinky 30-something in a formfitting little black dress and Manolo Blahniks that Sex and the City brandished in our brains. On previous dates, I’ve found myself catering to the idea of what a starter-pack caricature of an angsty Bushwick musician might want from me: more tattoos, ironic pleated skirts, belted skater chains clanking against my waist to accent a glinting navel piercing. While either might play into one convenient male fantasy, it does nothing by way of offering an honest-to-God peephole into my life.
“I think that’s where people get tripped up really easily. They want to play a part, or they want to put on a character when they’re dating, when, in reality, that’s going to make you feel so insecure,” Schiffer says. “I don’t think you should be dressing for a first date with your potential partner for the rest of your life in a costume, because then your whole relationship is based off of the person that you showed up as for the first date. And that’s not who you are.”
We cycle our way through oversize blazers, hip-hugging skirts, corporate button-ups, and adjustable trousers — all of which either exaggerate my favorite features (long legs, defined clavicle, a decent rack) or play down those I could part with. Two hours in, we settle on three key ensembles that work for scenarios of varying formality. For a “romantic candlelit dinner,” Schiffer offers a sheer, long-sleeved skirt set from the Frankie Shop with black Sam Edelman slingbacks (“It’s a little bit sexier but still feels comfortable, like we’re not going over the top”). For daytime, we land on a With Jéan red lace skirt with a striped button-up I already own. (“With a patent-leather slingback, we’re in Manhattan, and we’re going somewhere like Polo Bar; with Staud thigh-high boots, it’s more edgy Brooklyn.”) And for cocktails before dancing, we throw on a belted blazer — with nothing underneath. It’s not about dimming the offbeat elements of my style but, rather, about complementing or framing them to up the ante and refine what’s there. It’s an exercise in editing and restraint, without compromising on my beloved maximalism.
At the risk of lampooning her own business working with singles eager to attract partners, Schiffer acknowledges that her services don’t really change how datable you are. The inconvenient reality is that you can have a closet stuffed with gorgeous archival pieces and vintage Moschino pumps, and all of that can mean absolutely nothing if you don’t know who you are. Otherwise, you’re just a mannequin. And allowing yourself to dress well — to buck trends and invest in items that actually fit you, which (shocker) makes you feel like a bombshell — means finally throwing that mannequin out in the trash with the rest of your self-esteem hangups. What Schiffer’s hired guidance does give clients, however, is a sense of control and autonomy, when how they’re being perceived feels increasingly out of their hands.
“There’s an air of competition out there where everyone’s trying to stand out and trying to get the attention … like what’s going to make them different from the seven other girls whom some guy went on a date with?” Schiffer wonders. “I think that insecurity and anxiety is pushing people to want to try a bit harder or put more effort into what they’re wearing on dates, and I don’t know if I agree with it at all. There’s so much anxiety around the unlimited choices that people feel their outfit has to be perfect, or I have to show up perfectly, or I have to have the perfect shoe or the perfect bag. When in reality, none of it matters.”
What does matter, she reminds me, is my ability to show up as myself, clichéd though that may sound. Standing emotionally naked in front of a stranger who could end up being your life partner and asking politely not to be rejected or unfairly judged is humiliating, and there’s no getting around that. But of course, none of this is about acquiring new purses and belts, nor is it about throwing money at a problem. It’s about getting out of your own way so you can step into the person you are becoming — as it turns out, I needed a shocking ice plunge of a reality check that has both nothing and everything to do with clothes to come to terms with that. And if you’re curious, I did go on several successful dates (and one second date) in Coco Schiffer–assembled outfits. But I think Schiffer would probably tell you, as would I, that the clothes had absolutely nothing to do with it.
More From This Series
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- Why Allison Bornstein Wants Us to Rethink the Definition of ‘Timeless’
- What If My Personal Style Isn’t So Personal?