Photo-Illustration: by The Cut; Photos: Stephanie Geddes, Ashley Markle, Sophia Aerts
Maria Del Russo, a relationship writer and author of Simple Acts of Love, still remembers what she wore on her first date — a crisp February walk — with her now-husband. “I was comfortable and wholly myself,” she says. That meant vintage Levi’s, Doc Martens, a sweatshirt she’d picked up at a German thrift shop, and her mom’s vintage leather Eileen Fisher jacket. Her husband, Ben, remembers the outfit too. He still tells her, “Before the date, I saw you walking down the street and thought, That’s a girl I would want to go out with.”
The internet is full of formulas, rules, and outfit ideas to help you navigate the hellscape that is the modern dating scene, but a few too many TikToks offering “advice” and you’re just as likely to enter an anxiety spiral as find anything helpful at all. “What you put on says a lot about who you are as a person,” says Del Russo. As such, getting dressed for a first date is like piling up vulnerable moments, one on top of another, opening up the potential to be hurt if it all doesn’t work out. “People [online] can capitalize on that vulnerability by saying, ‘Here is the right way to do it,’” Del Russo explains. “But what they’re really saying is ‘Here’s what worked for me.’” Maybe this is obvious, but be wary of scare tactics thrust upon you by internet strangers; there is no outfit that guarantees success. Not to pull an Occam’s razor on you, but in reality the simplest answer is the best one: Be yourself. Easier said than done, sure — but with a few tips, you can narrow in on what makes a good first-date outfit for you specifically. That way, you can walk into a first date confident and focus on the real challenge: Keeping up a conversation with an internet stranger.
Photo: Sophia Aerts
No matter what outfit you settle on, the most important thing to consider before you walk out the door is how comfortable you are wearing it. “If you’re fidgeting because your dress is too tight or too short, or your heels are too high, it’s going to convey a message to the person across from you,” says Katie Lloyd, COO and matchmaker at The Bevy. Having to adjust an outfit constantly takes you out of the moment. You want to feel confident walking into a room, not be wondering whether your underwear is showing. As tempting as it may be to pick up something new for a first date, proceed with caution — you might not realize a top slides down or a new pair of shoes gives you blisters until it’s too late.
Photo: Stephanie Geddes
That being said, while comfort is key, there is a line to be drawn — especially when it comes to making a first impression. Lloyd recently heard from a client whose date showed up in sweatpants, “an indication of not caring and being unable to plan and prioritize,” he texted Lloyd afterward. Not a great introduction. Instead, let your outfit show that you want to be there but don’t feel the need to go over the top. And please, hold your partner to the same standard. If your date arrives in something sloppy or stained (God forbid they show up in a pool slide), recognize that they couldn’t be bothered to put a little care into how they’d come off.
The internet (and probably your group chat) is full of opinions, but don’t feel pressured to follow them. Maybe you’ve heard you should wear a dress, or wear red, or avoid anything flashy — really, that’s all up to your interpretation. “Something like color can influence perception,” says Lloyd. ”Sure, there is something to that psychologically, but I would never blanket tell someone what to wear.” In part, she explains, this is because nothing works for everyone. What if you feel like red doesn’t work with your skin tone? What if heels trip you up? Instead, she suggests choosing authenticity over rules: “Wear something that you feel really confident and sexy in. Don’t wear something because someone else said you’re supposed to.” If there is a tip you see online or hear from a friend that interests you, go for it, just don’t feel like your future romantic success rides on if you put on a bow or not.
Photo: Ashley Markle
Meeting at the museum? Wear the ballet flats that you can walk 10,000-plus steps in. Getting martinis somewhere swanky? Break out the dress that makes you feel like you’re one of the suitcase girls on Deal or No Deal. Part of feeling comfortable in what you’re wearing is knowing exactly how casual or dressy you need to be. Del Russo’s first date with her husband involved a walk in the park with his dog. “It had rained the day before and it was going to be muddy,” she recalls, “so I knew I had to wear boots.” If your potential partner is doing the planning, make sure you know exactly the type of date you’re going to be suffering through (kidding) — you don’t want to dress for the orchestra and find out it’s actually the rodeo.
Photo: Sophia Aerts
During her time as a relationship editor, dating was part of the regular routine for Del Russo. In one year, she went on more than 150 first dates — that’s one every two or three days. “I developed a formula,” she explains. Her go-to was black booties, jeans, a button-down shirt, and a leather jacket: “It was good for drinks, it was good for dinner, I was never worried that I was going to be in a place that was too formal — it always worked.”
If you (rightfully) find early dating to be intimidating, locking in on a formula that you know to be both versatile and comfortable. This can save you the annoyance of wasting hours in front of the mirror, feeling like nothing looks quite right. And yet as helpful as an easy formula can be, you don’t want to lean too basic and erase your personality altogether. Lloyd suggests, when wearing a simple outfit like jeans and a tee, layering on unique accessories like jewelry, a scarf, or your favorite bag, which will show off your personal style and suggest effort without actually being all that hard to do
When Del Russo was deep in her outfit-formula era, she found herself in a funny predicament: “I would date the same type of guy over and over again. They were all graphic designers who lived in Williamsburg and would take me to the same five bars and order craft beer.” As she got older and more sure of what she wanted, she also brought more of her personality to her outfit choices, something she feels ultimately led her to the right partner.
By leaning into the things that make you you, you’re also giving yourself a chance to weed out the people who just don’t get it. Maybe you love your long nails and a potential partner isn’t so sure about them, or you’re in head-to-toe designer and they’re more low-key. Who knows, they may still be the one for you! If that’s the case, being yourself won’t scare them away. After all, what is a first date but a chance to explore if there’s a spark between you and a total stranger. The quicker you bring your true self to the table, the faster you move past the people who were never going to be right for you anyway.
