I’ll spare you the details of my protracted, Piscean search for “true love” that has taken me through several relationships, heartbreaks, and MANY first dates both abject and awesome. Unless (as happened this week) my first date happens spontaneously and unexpectedly and I don’t have time to change out of the chafing pseudo-work duds I wear to the office, I try to dress tactically for a first date. The most important factors in a first date outfit (IMO, as always) are comfort and potential.
The former is self-explanatory, the latter I like to think of as walking the line between sartorially functioning as a blank canvas onto which your prospective lover may project their desires and designs for the future you two could share and having a visible personality that doesn’t render you as a soulless husk (think: showing up to a date in head-to-toe beige athleisure).
This manifests in clothing that is relatively simple in shape and color but has interesting, thoughtful details. You also want an outfit that, in case you meet your soulmate wearing it, will feel good as a talisman of love for years/decades to come but if you just get mediocre soup with another schmo won’t be irredeemably tainted.
Of course, this is all assuming that you actually want your date to be able to envision a future with you. If you are “dating viciously” or “antagonistically,” you can ignore all of these recommendations. I’ll write a post on antagonistic outfitting soon enough.
I’m assuming that your first dates are as relatively casual as mine typically are (god forbid the Moonstruck-style first date at the Opera) but I’ll still separate this guide into “more casual” and “slightly less casual” categories because that seems to make the most sense!
My most controversial quality is that I LOVE a boat neck, and this one is super evocative while still remaining casual. They’ll want to play with the snaps around the neck. Mission accomplished.
Another white tee with a playful hardware detail! If it’s good, it’s good!
I like the elbow-length sleeves and the shape of the collar on this tee! Buttoned-up without being self-serious.
I love the subtle but bright colorway of this shirt, which apparently has “side vents with hidden snap fastenings” in case you get sweaty in the presence of a hot person.
I would either pair these pants with a plain off-white tee or go balls to the wall and wear this full suit. The muted color palette keeps this from looking clownish but it still suggest that the wearer is Here For A Good Time.
The goal of these pants is to implant an artificial sense of nostalgia in your potential match, making them associate you with the wistful dusks of their adolescence. By the time the date is over they’ll feel like they have known you for decades.
These pants look like the awning of a perfect Greek diner in Queens on a sunny Spring day. Cute date idea! Though maybe save these pants for a less on-the-nose occasion. I own a different-patterned pair of Chefman pants and they are so comfortable and durable they always make me feel confident and competent.
This is my go-to first date uniform! The colored jumpsuits can be a little cutesy, but the black is simply perfect in its fit and structure and is ineffably cool. Only issue is if you end up at a scummy bar, as many of my dates are wont to, the suit might touch the bathroom floor when you have to go pee. Develop a disrobing strategy and practice before your date.
I don’t really have much to say about this parka. It’s casual without looking sloppy, the fabric is sturdy and interesting, and the shape is unique. It just looks nice.
Pretty much any Misu A Barbe hat would be horrifically adorable on a date but this is a FIRST date so we are keeping things a little less cloying with a beanie! Nothing says “I haven’t decided whether or not I want to have sex with you yet” like sporting a beanie! Keep ’em on their toes!
On most of my *good* first dates I end up getting in 20k steps or so because we get restless, move to a second location to avoid the karaoke night we did not know was going to be happening at the first bar we chose, or we spontaneously decide to walk across most of Manhattan because I direly need a cup of borscht right at that second (the *good* dates usually play along with these whims). I have a really fucked-up ankle from a years-old injury that has radiated into fucked-up knees and hips, so walking a ton is tragically difficult for me, as someone who loves to walk. THESE SHOES CHANGED EVERYTHING FOR ME. I CAN GO ON MARATHON DATES AGAIN, FOR BETTER OR FOR WORSE.
I have this exact watch but it’s very broken. I might order a new one because of the price point and just how many people have been impressed/amused/confounded into infatuation with me after a first date solely because of this watch. I’m probably exaggerating but maybe I’m not.
Slightly Less Casual
This button-down is extremely sexy in its prim shape and clingy fabric. The buttons down the back are erotic. The only thing I would change about these is the cabbage-y hems (one of my pet peeves, they make everything look 50% more like an item that would be sold at Urban Outfitters) but since the blouse is dark it’s not as noticeable and meets my harsh first date standards. More than most of the people I’ve dated in the past year can say.
I think by now you all understand how much I love a garment that can be worn in multiple ways. Think of the potential. You can excuse yourself to go to the bathroom, come back in an essentially different look, and judge your date’s perceptiveness by seeing if they notice this change.
This shirt is fun, evokes motion, and is enjoyable to look at without being overwhelming!
You can EASILY find a dupe for this shirt in a thrift store. Its preciousness and its sexiness neutralize each other, making it perfectly first-date-appropriate.
This shirt looks sharp without being overwrought and evokes a kind of cowboy laissez-faire without being costumey (hey, for the love of god, unless you’re going to a RODEO, please DON’T wear a suede fringed jacket or a ten-gallon hat to your FIRST date. Yes, I have been on the receiving end of this move. There was no second date [not because of the sartorial decisions, but those didn’t help]).
This suit makes you look like Madeline (the 1939 boarding school darling) grew up and became the CEO of Verso books. Looks luxe and a bit posh but not overly capitalistic or grotesque. Excellent collar, color, and button size. Don’t love the presumably fake pockets but I still fuck with the fit.
The subtlety of the twisted shoulders will force your date’s eyes to HONE in on your collarbones, where they will stay for the rest of the evening, inducing sexual but respectful thoughts about kissing them.
The “scales” on this jacket provide visual interest, the hardware makes you look badass, and you caqn wear this jacket to literally every first date you go on for the rest of your life without it getting tired because it’s a fucking leather jacket and will never go out of style.
This is another one of the rare HR picks I actually own myself. Each necklace is unique, which makes them feel like talismans. Maybe your ring necklace will be the harbinger of an eventual ring on your finger hahahahaha probably not this is your 6th Tinder date of the month and two of them, differently gendered, have been named Charlie and both of them ghosted you immediately after you rounded the corner post-goodbye. But this necklace pays homage to your most romantic inclinations while avoiding gaudiness or a cringe factor.
Thanks for reading! Let me know if you have any hellish or heavenly first-date-dressing stories, I am a Pisces with fashion brain worms and eat that stuff up.