Whether it’s your first date or your four-hundredth, finding the right date-night outfit rarely feels like a simple task. Regardless of how much pre-date shopping and planning you’ve done, the hour leading up to leaving your house is fraught with indecision, a closet floor full of rejects, and many FaceTime calls with your closest friends.
A solid date outfit isn’t just about leaving a good impression. Throwing together the perfect ensemble can often feel like an overcomplicated equation. You’re made to balance out a myriad of elements like the time of day, location, weather, and how much walking will be involved—whether it’s with a long-term S.O. or a very new flame.
And with Valentine’s Day coming up, date night is at the top of mind. While we’re always up for giving you our advice on the matter, this time around, we’re crowdsourcing for date-appropriate looks that have been tested and approved. We figured it’d be best to go out into the Instagram wild and suss out what our NYC-based style muses actually do and don’t wear on dates. (Spoiler: Slip dresses are in and fussy heels are out.)
So the next time you match on Tinder, take advice from these six stylish women as they dish on the outfit combos that are sure to wow.
My go-to date-night outfit: With Valentines Day creeping up, I’m already plotting the perfect date-night outfit. My usual go-to is a slip dress because you can easily dress it up or down depending on where you are going. In the wintertime, I love to layer the slip dress over a patterned long-sleeved shirt and some knee-high boots for some added warmth. What I generally avoid: While I love to layer for warmth, I try to steer clear from layering too much. I remember a sit-down dinner date dinner where I started sweating profusely because I had two sets of leggings on under my skirt! Let’s just say I learned my lesson.
My go-to date-night outfit: When Collin (my boyfriend) and I head out for a date, it usually involves a lot of food and drinks—especially wine or beer. He’ll probably also pay zero attention to my outfit. So I usually take the approach of wearing something I feel bomb in. If I feel great, he picks up on that and it all contributes to the general merriment of the evening. That said, comfort is key. I love a printed pant with some stretch or a colorful skirt that I can wear a cozy sweater with. What I generally avoid: Anything that I’d have to unbutton after a big meal is a hard no. There’s nothing that makes me feel less sexy than having to unbutton a tight pair of pants after my individual 10-inch pizza. This isn’t even a rule I stick to just for dates—this is pretty much a life rule for me.
My go-to date-night outfit: I love a good pair of high waisted, straight-leg jeans with a silk top (preferably a crop top). I finish off the look with pointed-toe heels and a mini handbag or pouch. It’s a semi-comfortable but bold look. It’s a look that tells people you’re chic but effortless too. What I generally avoid: Tight tops. I’m not the type to shy away from throwing down a good meal that may leave me with an inevitable food baby. If that’s a possibility, I make sure to wear a blazer or a silk loose top and maybe a pair of fitted jeans to balance out the look. Or I’ll do the reverse and wear a pair of loose jeans with a fitted top. I always make sure to wear a light leather jacket over the combo just in case I end up indulging at dinner.
My go-to date-night outfit: If you invite me to anything—and I mean anything—I’ll use it as an excuse to wear a look. Date night is no different. I use any date with my boyfriend as an excuse to be extra as hell and test out new pieces or a new styling idea I’ve been dying to try. Besides, since my boyfriend has to love me, it’s a good time to use him to snap my outfit picture for Instagram. What I generally avoid: While I like getting creative with my look, I always wear comfortable shoes. One too many times I’ve made the mistake of wearing sky-high platforms or a pair of narrow boots that made me want to head straight home after dinner instead of spending doing something fun after. I’ve learned to pair my look with my go-to Naked Wolfe platform sneakers or Dr. Marten Jadon boots. It helps me to avoid spending half the date complaining about my feet and saves my boyfriend from having to carry me home (it’s cute, but I’m pretty sure he’s over it after the fifth time).
My go-to date-night outfit: My go-to date look starts with a high-neck bodysuit. I used to wear ones that would show a generous amount of cleavage, but my roommate has trained me to save some room for the imagination (LOL). I then pair it with a straight-leg jean and always a heel. My outfits are usually all black—simple, sophisticated and sexy. What I generally avoid: Traditionally, I steer clear of anything that feels too “romantic” or “girly” (like a red dress or a delicate flower print). I think first dates are about capturing your personality while also retaining a touch of mystery. I also make sure to never wear something I’m not comfortable in. If there’s an outfit that requires my boobs up to be taped up with multiple strips of double-sided tape, it’s not it. First dates should be about the conversation and the spark—not about whether your tits are lopsided. Trust me—I’ve been there, and it’s stressful.
My go-to date-night outfit: For a night out, I typically want to wear something that makes me feel cute, but comfort is still paramount to me. I’ve been enjoying wearing a short silk slip dress with high-heeled boots. The thicker the heel, the better. If it’s cooler out, I will layer with an oversized blazer. What I generally avoid: I try to avoid anything that makes me not feel like myself. I always want to have fun, but not at the cost of wearing something that feels like it’s too tight or like I wouldn’t wear some version of it with my friends on a girls’ night out.
