Mastering the Art of a First-Date Outfit

My fail-proof formula.

first date

Someone once told me they had a friend who went on three dates in one night in order to maximize a really good outfit. While it’s likely this was lore, the concept is brilliant—no mussing and fussing over what to wear, three times through. And while we can all agree that dating is hard enough without having to factor in an outfit—who you’re dating, where you’re going, the weather forecast, etc —the minefields you and your closet face when mastering the recipe for a perfect date-night look can be endless. So, I’ve pulled together a few tried-and-tested tips to help you master the art of date-night dressing.

Comfort Is Key

When I picture a stereotypical (but killer) date outfit, an impossible equation of dark colors and sexy cuts somehow come together in a chic but subtle way. In practice, this is most definitely not the case. After much trial and error, I think I’ve finally cracked it: Comfort is key, and while I’ll make an argument to stop short of sweatpants, being comfortable in what you’re wearing on a date should be prioritized above all else. It’s important to feel good in what you’re in, and this likely translates to all other aspects of what makes a great date, aside from a great outfit. Environment can also play a big factor in this theory. If it’s cold out, don’t opt for the skimpier jacket. If you’re going to a dive bar, leave the heels at home. Below are some options that work for just about any occasion and won’t have you questioning your choices over and over.

The Perfect Combination of Sexy and Cute

The perfect combination of sexy and cute is the gold standard for nearly everyone on date night. It requires a foolproof recipe of good conversation, fun environment, and, of course, a not-too-sexy-but-also-not-too-cute outfit. I personally think wearing a turtleneck is a power move, but you have to style the outfit well in order to differentiate it from one you’d wear to visit to your grandparents. You don’t want to overdo it but also want to do just enough—this is a date, after all. And while the time of a date is most definitely a factor (a Friday night look may let you get away with a little more than a Tuesday morning coffee), I usually prescribe to the less-is-more rule. This is not dissimilar to the perpetual desire to channel the cool and effortless look that so many of our style icons seem to have mastered. This old thing? Oh, I just threw this on. There’s nothing cute or sexy about an outfit looking like it took as much effort as it likely did, so I usually try and fake it ‘til I make it on this one, but pieces like these usually do the trick:

Accorta Top


Make It Personal

I used to adopt a mentality that I should dress for my date, not myself. This likely is a result of not having a “type,” which means the options can be endless depending on who my dinner partner may be. Not only can this be exhausting, but I found that it never truly reflected what I would have worn if I were dressing for myself. Everyone’s wardrobe has elements that make it theirs, and I’m a firm believer that some of these beloved components should make it to the first-date party. Whether it’s a pair of earrings or your favorite hot-pink pants, that’s for you to decide—but whatever the decision, be sure to make it a personal one. First impressions count, so yours might as well be of yourself.

Part of the series:


You May Also Like