Hey Fashion Friend: I’m Dating Again. What Should I Wear Out?

Video: The Cut

It’s getting hotter in New York. The tree outside my apartment just started blooming. I took the quilt off of my bed. I even shaved my legs this morning. After a period of hibernation, I think I’m ready to come out of my shell and start dating again, and readers seem to feel the same. But what to wear? When I posed the question on Instagram, I was naïvely surprised to see that so many of you have been out. You’re not waiting for any stupid groundhog to give you the go-ahead. You’re putting on your leather mini skirts, backless bodysuits, and Margiela Tabi boots and hopping on the backs of motorcycles with your crushes. It’s inspiring! Below, all the insight I gathered from other people’s escapades.

If You’re Nervous, Try a Uniform

Years ago, there was a period of time when I was going on enough first dates that I felt like I needed a dating uniform — something that worked in most scenarios, that I could just confidently throw on without thinking. “It’s so much easier,” said one reader of the practice. “I feel like if I don’t wear a consistent outfit, I’m worried about being uncomfortable and how I look.”

My own uniform consisted of a black turtleneck and jeans: simple, smart, and flattering. But also deeply unoriginal. A friend offered a different, but similarly casual formula: either a Reformation top and jeans, or a black shirt dress with knee-high boots. None of these looks scream “date night,” which is the point. You could probably wear them to the office and no one would be like, Where are YOU going?? [Insert embarrassing wink face.] They spare you from putting in too much effort, and they telegraph this same attitude to your date: You’re not going to bend over backwards, unless it’s worth it.

Your dating uniform doesn’t have to be a snooze, though. One reader told me they wore a “full joutfit” with a gold belt on two different dates recently. Another said they like to wear big earrings with their T-shirt/turtlenecks. (I recently invested in these.) And lipstick always helps. “Jeans, sweater, no bra, heels, big curly hair, bold lip,” said another person of their go-to first-date outfit. Carrie Bradshaw would approve.

Your second-date uniform — should you make it that far — can also up the ante. My friend, for example, said for second dates she wears “either a slip dress with a little shirt over it, or a funkier top.” So, something flirtier, with more personality. (I’d try something sheer.)

No one I spoke to has a third-date uniform up their sleeve, which seems like a good thing, but also maybe speaks to the effectiveness of the practice in general …

Dress for the Rom-Com You Want to See

We could all use more reasons to dress up, and going on a date is one of them. I would even go as far as saying that dressing up is the entire point. It was thrilling to read the descriptions of some of the more formal, or on-theme outfits you all have been wearing lately. This one, for example, had me swooning when it landed in my inbox:

Wore a black leather double-pleat trousers, black FW 1992 Yohji double-breasted blazer, and black Margiela Tabis on a first date two weekends ago with someone I’d had a crush on for years — he picked me up on his motorcycle (I’d never ridden one until then!) so I knew I had to dress the part. Lost a chunk of the stacked leather heel on one boot while keeping myself from flying off the bike but it was absolutely worth it. Kissed me good night when he dropped me off, we’re planning on meeting up again.

They got the gig! Bravo. A few of you also told me you wore corsets on first dates, which feels very Bridgerton. (Here’s hoping your slow burn doesn’t last eight weeks.) Maybe try styling it like Prada Fall 1999, instead?

Some of you also suggested wearing eye shadow as a way to add some glam, and accentuate your smoldering gaze. One person told me she channeled Elizabeth Taylor’s beauty look in Ash Wednesday for a fifth date and it “worked.” Another told me they went full GoodFellas wife for dinner and a movie:

It’s been about six months. I wore a black and white swirly dress from a brand called Another Girl with a tight black turtleneck underneath, sheer black polka-dot tights, Doc Marten monkey boots, a gold chain necklace, lilac hoops, and blue eyeshadow because every day I want to be in that scene in GoodFellas when all the wives are pampering themselves.

If you want something even more dangerous, you could also watch some erotic thrillers for inspiration.

Wear Fabrics That Feel Good

As with dating in general, it is possible to be both casual and formal at the same time, although it is a delicate balance to strike. Maybe show a little skin with a crop top and low-rise jeans, or wear a shirt with a low-cut back. One reader said of their backless bodysuit: “It didn’t reveal much, until I turned around for a surprise.”

Here are three examples of more advanced outfits readers submitted that I think do this especially well:

  • Suede mini skirt, tall Prada boots, white T-shirt, and a leather coat.
  • Muted Bode one-off shirt, vintage Levis, loafers, and a fur coat.
  • Navy blue Pleats Please mockneck top with cropped black pants and pointy black boots.

You’ll notice that all of these looks include some sort of sexy material, whether it’s suede, or leather, or fur — or a manipulation of a fabric, like pleats. When choosing an outfit for a date, I think it’s important to not only think about how it looks on your body, but also how it feels. A silk shirt, velvet, or anything leather can help get you in the mood, and turn the person sitting across from you on. As one particularly fabric-conscious person told me, a leather mini skirt also slides off more easily when you wear it with tights.

Put It All on the Table! (Your Style, I Mean)

The last time I went on a really good first date, I decided to ditch my normal uniform and wear something that felt more me: an ankle-length, tiger print Rachel Comey dress. It was tight but not body-con, and made out of a stretchy, sweat-proof, almost bathing suit-type material. It may sound weird, but it was perfect. The night was perfect. And I really do think my outfit — or at least the act of choosing said outfit — had something to do with it. At first, I was hesitant. I thought it was maybe too much, and I was nervous about coming on strong. But I was also genuinely excited about this date, and didn’t want to hide it. Why should I? I figured I might as well put all my cards on the table from the jump, and not waste anyone’s time. If he didn’t like what he saw, well, then it was never going to work.

A lot of you wrote that you wore your most style-forward outfits on first dates, and I’d have to argue that this is the best approach. Be bold! Dating is supposed to feel a little bit like jumping off a cliff, and if you’re dressing like you’re interviewing for a boring desk job, (as I have), then maybe you’re not really in the mood to be dating at all. On the flip side, if the person you’re on a date with can’t handle your style, then you’ve got your answer: Good-bye. One reader said she wore white printed Saks Pott logo tights on a date and a guy called them “designer leggings” with disdain. Next! Another reader told me that when a guy “didn’t even notice” his incredible, vintage white Versace cargo pants with a gold medusa on the butt that it was also a deal-breaker. Respect. The dates that get it, get it.

Some Other Helpful Tips:

  • Don’t wear your favorite earrings if you’re considering sleeping over. Let this message I got from a reader be a lesson: “Lost earring in his bed. Didn’t wanna hang again. Had to retrieve when he found it later. He thought it was another date. Bad vibes.”
Hey Fashion Friend: What Should I Wear on a Hot Date?