What Makes a First-Date Outfit “Good”?

Dating again in New York City feels like a cat being thrown into a pool. I am confused and displeased. I am barely able to keep my head above water. Somehow everyone watching me finds my attempts at navigation amusing.

But after eight years of serial long-term monogamy, here I am: A curmudgeonly wet cat emerging from the shallow end of a pool, finally ready to settle into casual dating with no particular endgame in sight. Liberating! Empowering! My therapist is thrilled for me. I have no idea what I’m doing.

Don’t get me wrong, I’ve been single for periods of time in New York and have dabbled in dating. (The sheer STRENGTH required!) It never took long, though, before I had latched onto someone and formed a cute codependency. But I’m trying to resist my old impulses, which is why this new era feels fresh and particularly rife with possibility. I want to walk out on a first date when they tell me they want to touch my feet! I want a boy named Chad to fall asleep on me at dinner! I want to force someone into a pierogi crawl that starts at 11 a.m. and ends when we feel like we have to puke! And I need a solid, First Date Outfit (FDO) to do all of it.

There is an undeniable art to the FDO. I know what I’m typically drawn to: pants so tight I have to shed them like a snake, a sweater that exposes a clavicle or perhaps ~two~, etc. but I knew there had to be a real formula for happiness that pushed me out of wearing an innocuous jeans and tee (incidentally, what I wore when I met my previous partner of two years). I asked the Man Repeller audience for the criteria that are paramount when it comes to putting together a look and behold, they/you delivered:

  • The outfit must be comfortable and make you feel comfortable. It should have nothing that you have to fidget with, and nothing that makes you feel like you’re a different person.
  • It must be a balanced combination of trying, but also not trying. It should look nice enough to look put together, but casual enough that you don’t look like you spent hours overthinking it.
  • It CANNOT show sweat or hold odors.
  • It must include a subtly flirtatious element like a hint of a bra, a soft sweater, a heel, or jeans that make your butt look amazing.

With those in mind, Harling Ross and her flowing locks came to my aid. She styled me in four first-date looks that ticked every box, and I’ll be keeping them in my back pocket for eternity. Because I may be single for that long lol.

That’s Business, Baby

When I put on all the components of this outfit, I felt like a real business binch. For those of you with workplaces that are a little more buttoned up (literally), this felt like a perfect work-to-drinks option. The pants I could probably do the splits in, if I was capable of doing the splits, and the camel blazer brought the woo-woo-ness of the sequin shirt and sparkly ballet flat back to earth. It achieved all the criteria: comfort, trying but not trying, not sweat-tastic, and flirty because if you have what Amelia Diamond calls ‘Magpie-Itis’ then you will either be drawn to me or have my shoe in your mouth by the end of the date. Win!

Did I Stutter When I Said “Come Hither”?

When Harling put me in this second look I truly felt sexy from the second I stepped out into the foyer. This set from Staud is, as Tyra once noted, “Hoe but make it fashion.” The trousers are nice and long and–SURPRISE!–the top is actually cropped! Pairing it with an oversized sweater is totally something I would do to make myself feel completely at ease. Especially when that sweater slips oh-so-gently away from the shoulders. I felt comfortable, confident, and STEAMY! Are you warm?

Buy a Girl a Drink First!

I love this outfit so much, partially because it just feels so Harling to me, and partially because it delighted me by being something that I didn’t think I would ever wear but absolutely would now that I know how it makes me feel! I never think I look good in skirts, but something about this starchy one paired with the tights, knee-high heeled boots, and a bevy of layers on top made it feel just really right. I insisted on the velvet bow in my hair to complete the look. I felt comfortable, I felt elegant, I felt pretty, and I could absolutely walk a museum mile in this. Though not a great option for that one type of person who insists on making your first date the climbing gym.

Oh, I Didn’t See You There Because I’m Very Vision Impaired

I love this look. I wouldn’t say it reads overtly feminine or sexy in the way that some of the others do, but that’s also very moi. This outfit says: I’m ready to tell you that I think your passion project needs a critical eye or Do not try to pretend to be more online than me because you are decidedly not. It was comfortable, it was cotton for minimal pit sweat, and it made me feel like I embodied a cool effortlessness.

I hope that at least one of these has inspired you to switch up your requisite FDO. It certainly has rocked my world and ushered a veritable FOUNT of date-night outfit ideas for the dates that hit, the dates that flop, and the dates that make for a great story. Now New York’s Most Eligible Bachelorette just needs to… book one lol.

What’s your perfect First-Date Outfit formula? Any criteria we missed? Meet me in the comments section with a glass of wine and good conversation.

Styled by Harling Ross. Shot at Legacy Records.

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