What to Wear on a First Date: 3 Summer Looks

Three first date outfits for any occasion—from a baseball game to a rooftop happy hour.

The biggest dilemma before any first date is always what to wear.

I’m partnering with Coffee Meets Bagel to help you find the perfect first date outfit—and the perfect first date.

Coffee Meets Bagel is a free dating app that curates just a few matches for you each day—usually people you have mutual friends with—so you don’t have to swipe through endless profiles of guys you’re not into. They’re launching a brand new #LadiesChoice update, which means you’ll now only see matches who’ve already said they’re interested in you, putting you in total control of who you match with and talk to.

I first heard of CMB on Shark Tank last year, and then a few months later my friend was telling me about his new girlfriend who he met on the app (they’re still together, now living together!). One of my coworkers also met her boyfriend on the app, so I thought I’d give it a try.

These three super cute first-date outfits are inspired from looks my friends and I would wear on a summer date. Check them out and let me know which is your favorite!

1. ripped jeans | 2. off-the shoulder top | 3. shoes | 4. bag | 5. ear climbers

If you’re going on a casual day date, this outfit is perfect—cute and comfy and it doesn’t look like you’re trying too hard. Off-the-shoulder tops are such a huge trend for summer, and I love the look of a fresh white top with ripped jeans and Converse. The ear climbers add a little edge, and this Rebecca Minkoff crossbody bag is my summer go-to. In need of a few day date ideas? Check out the zoo, go to a baseball game, or do something touristy in your own city (like spending the day at Navy Pier in Chicago!).

1. romper | 2. sandals | 3. gold cuff | 4. necklace | 5. clutch

A romper is the perfect day-to-night piece, and it’s so easy to dress it up or down. This cold-shoulder romper is one of my favorites (my friend Kelsey wore it on the 4th of July and it was so cute!). It’s a great look if you’re headed with your date to a street fair, music festival or a rooftop happy hour. (Check out more of my favorite rompers here!)

1. black dress | 2. lace-up sandals | 3. crossbody bag | 4. earrings

A classic black dress is always a good idea for a first date, and this high-neck scalloped dress is so cute and such a great price. I love dressing up an all-black look with bright accessories in the summer, and these orange and turquoise earrings are a great statement piece. Rooftop cocktails is my summer date of choice, but dinner at a cool new place that neither of you have ever been to before is another fun idea.

Now that you’ve got the look down, you’re ready for your date! I’m a big fan of the new #LadiesChoice update (it takes the anxiety out of online dating!), and now that it’s available to everyone to download, you can try it out for yourself. Click here to download the Coffee Meets Bagel App.

Happy swiping!