What to Wear on a First Date? We Asked the Experts!

No matter how you cut it, first dates are usually preceded by a lot of nerves, at least a little bit of panic, and handful of jitters sprinkled on top. The stress sets in, and before you head out the door, you second-guess absolutely everything—including the outfit you picked out after frantically googling “what to wear on a first date” all day.

Listen up: when you’re dealing with first-date nerves, the last thing on your list of stressors should be your outfit. First dates aren’t the time to reinvent the wheel when it comes to what you’re wearing; it should be something you know you’re comfortable in, and we’re here to help figure out exactly what that is.

Whether you’re heading out on a daytime coffee date or have reservations at the cool, trendy new restaurant in town, stop typing out a frantic text to your group chat, and leave the outfit planning to us. 

Do’s and don’ts

Do

• Wear something you’ve already worn and know you’re comfortable in
• Break out your pieces you usually reserve for special occasions
• Think about what makes you feel the most confident

Don’t

• Wear a brand-new piece that risks being uncomfortable, like needing to mess with a falling strap or digging-in waistline
• Try to dress in a way where you won’t feel like yourself
• Overthink it

Daytime Coffee Date

A daytime date poses a little bit more of a question mark than something like a dinner or drinks date might, but it should be approached as being that much simpler. 

This is all about elevated basics. A cute pair of jeans, tank, and sneakers exudes just the right amount of effortless while also being ultra-flattering. If you run cold, make sure you bring a layer to throw on top, so you aren’t worried about your temperature more than hitting it off with your date.

Casual Dinner Date

In our experience, a casual date’s vibe can be more difficult to strike than one that veers more on the fancy side for one reason: the fear of feeling overdressed.

To keep it as simple as possible, opting for a casual dress is the easiest and best bet. You’ll feel date-ready and like the event is a little special, but won’t look like you tried too hard. The best part? It’s a one-and-done look, so your pre-date stress will be kept to a minimum.

Post-Work Drinks Date

A post-office drinks date is, in our humble opinion, one of the best types of dates you can have. It automatically feels like less pressure because you’re already out and about, and if you’re anything like us, have talked about every possible thing that could happen during the date with your coworkers all day.

Since you’re coming straight from the office, arriving in a look that’s office-appropriate is expected. We’re partial to a tee, blazer, jeans, and a pair of sneakers to hit the nail on the head of “working woman heads on date.” If you want to make it a little sexier, opt for a more form-fitting tank rather than a tee under your blazer.

Elevated Dinner Date

The most classic of dates: a nice dinner out. Rather than messing with figuring out a pants and top to wear, a dress is the best bet.

To make it a little more elevated, a midi-length dress is a great option for a nice restaurant. It’s easy to make work for a wide variety of locations and finding one you’re comfortable in is a great go-to to turn to whenever the nice-date jitters turn up.

Picnic or Outdoor Date

After 2020, the rise of the casual, outdoor date is here, and it’s a whole new variety of date to have to navigate the outfit waters of. To combat the questions, we’re taking the nap dress trend and running with it.

When you might be sitting cross-legged on the ground, you don’t want to mess with tight jeans or a risk of feeling uncomfortable the entire time. A long, casual dress not only screams picnic, but will make sure you can sit and maneuver any way you like all night long.