My first date track record is hit or miss, but I chalk that up to chemistry and not what I wear (thank you very much). When I’m picking out what to wear on a first date, I’m a creature of habit. Having spent a few years navigating dates with strangers, I’ve made a habit of deliberately dressing normal, which for me usually entails jeans with a T-shirt or dressy top and a pair of comfortable shoes. Despite what that description may lead you to believe, that’s not to say I don’t put in effort. Simply, I’ve realized that as a distinctively low-key person, I want a first impression to be an honest representation of who I am.
Still, since dating is a process that’s a bit of a closed feedback loop (it’s rare, and frankly weird, to get a review afterward), I was curious to know how other women dress for a first date. So I decided to reach out to single friends on social media and hear about their habits for date night dressing. The hope is that crowdsourcing other women’s tricks for a first date will make things just that much easier for you the next time it’s your turn. Read on to learn more!
“Jeans, a T-shirt, and lots of delicate jewelry! It’s the most understated form of sexy and makes me feel like my true self.” “T-shirts mostly. Why do I need to pretend I dress [girly] when most of the time I don’t?”
“Vintage Levi’s, a little black top, and cool heels every time.” “Low-cut top with the best jeans and some sort of platforms and hoops.” “Something cute but casual. A favorite pair of jeans is always a good staple to start with because you’re automatically comfortable and you know you look awesome.”
“Comfortable and not fidgety. The pièce de résistance is my earrings. I have a bunch of fun but not overpowering statement earrings that draw attention to my face, eyes, cheekbones, smile, and then earrings.” “I think jewelry is important. The other person may not notice those small details, but they add up.”
“I always wear a little block heel on the first date. I’m 5’3″, so typically a little height makes me feel more comfortable overall. However, a block heel is also a great choice in case you don’t know for sure how tall your date is. If he is on the shorter side, a block heel won’t come off as intimidating, and if he is taller, then you just look plain cute.” “I’m not a very tall girl, but if I’m going on a first date with a guy I met on a dating app and I don’t know his height (I don’t think guys have to divulge their height on dating apps, but a lot seem to…), I’ll always wear a low shoe like a bootie or kitten heel. I figure that if it turns out he’s not very tall, we’ll at least see eye-to-eye.”
“I wear a big dress like normal.” “When all else fails, Réalisation Par’s Alexandra dress. That seems to be my go-to back up.”
“Dress and sneakers always! It keeps you comfortable and can show your personality.” “Personally, I love just a great-fitting retro or plain tee and a killer heel, fun sneaker, or statement bootie. For first dates, it’s more about the little details.”
