Summer First Date Outfits, As Selected By An IRL Couple

Summer First Date Outfits, As Selected By An IRL Couple
Photo: Cam Zhang.

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What do the cool girls wear as a first-date outfit nowadays? I’ve been dealing with the conundrum of what to wear out in the heat this summer, and even though I have a boyfriend, I still contemplate the age-old question of how much effort to make on the first date. In my continual effort to overhaul and refine my closet to tastefully keep up with trends, I’m always investigating how TikTokers approach their wardrobe. 

Having my Gen Z in-a-band boyfriend as a stylist definitely helps, and he killed it as a budding fashionista concocting a concert outfit for me. Since I’m still in the honeymoon phase of trying to impress him even in the humid summer temps (we just made it official earlier this year), I consulted him for a faux summertime “first date” fit. I was curious about what look he envisioned me in on, say, a first date in the West Village for drinks and apps. 

Before he dived into his picks, all he said to me dead in the face was “you’re gonna hate me. It’s cute, it’s just not your vibe.” Fun first words. Below, the trendy first-date ensemble he chose for me—and what I would have chosen myself. 

 Summer First Date Outfits, As Selected By An IRL Couple

Cam Zhang.

What My Boyfriend Chose

My boyfriend chose the above ensemble for our faux first date look, and he considered what the expectations would be after the requisite Insta-stalking. “This potential partner’s probably been in your DM’s for a couple weeks, so first and foremost it’s important to wear something that is consistent with the pictures you usually take,” he said. “You don’t want to be a cottagecore girl on Instagram, but in real life, you’re emo. You want consistent branding.” I had no idea men contemplated digital branding in such depth. 


New York gets wet and humid—swamp butt is a very real struggle to accommodate for. Z’s suggestion is to go with a very billowy minidress of any color or pattern. You’re able to flaunt your assets while simultaneously being comfortable in the heat. “Instead of showing traditional things that you want to show off in your body, you’d be showing more nuanced flavor. It’s something that wouldn’t make your mom cry if she saw it, but enough to probably give her grandkids.”


Z selects out a strappy black sandal with a small heel for footwear. “We don’t praise nor shame foot fetishes,” but he picks this out due to practicality and style. Socks will make you sweaty, while a tall heel will make you feel uncomfortable. A small heeled sandal will eliminate the problem of you towering over your date, just in case they were lying about their height online. 


Hold your belongings in a clutch, because at some point, if your date is a decent human being, they’ll offer to hold it for you. “It’s sleek, minimal, and elegant, and it looks like you can afford more than the chicken tendies you just devoured.” 


For jewelry, Z recommends avoiding rings, as rings of any sort subconsciously signify commitment, and you’re scoping out if you want that from them yet. A dainty necklace paired with the dress will help accentuate your neck and shoulders, as well as become a conversation point. Small earrings, such as pearls or studs, will help tie the whole look together. 

gen z boyfriend styled

Cam Zhang.

What I Would Have Chose

I once read somewhere that a first date doesn’t deserve to see you in a dress yet, because to me, a dress is a top-tier outfit. While Z’s picks gave off a divine soft feminine energy, I want to ensure my first date knows I’m a gaslight gatekeep girlboss with a 9-5, and I don’t have time for them to play games. 


I’d go for a classic oversized blazer over a comfy yet cute knit crop top. The blazer reminds your date you DO in fact have a job and are independent without them, while also keeping you warm under any unnecessarily high AC inside. The crop top serves as a sexy piece underneath, which you can always reveal by taking off your blazer as the night goes on.


I’m all about blending cozy with sleek, so a high-waisted, slim hem ribbed black legging is my go-to here. The high-waist will hold you in and keep you covered up in just the right ways with the crop top, while the slit hem is a classy polished detail designed to show off some hot footwear. Black is universally flattering and, most of all, will hide any accidental food stains.


I actually agreed with Z’s shoe choice. I’d pair the high-waisted slit hem leggings with the strappy black heeled sandals. It’s easygoing, elegant energy you exude via footwear while you balance both business and sex appeal on top.


Since there are pockets here in the blazer, I’m a fan of foregoing a purse when possible. Tie the whole boss b*tch look together with gold mini hoops and sophisticated modern rings to show off your fresh mani.

Ultimately, wherever your first dates end up being, Z and I agree on the following. He notes, “the best thing you can wear on a date is the thing that makes you the most comfortable. A real date will not be concerned with the fabric on your body, but the words out of your mouth.” Amen.

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Image: Getty Images. Design: Sasha Purdy/STYLECASTER.