Top: Zara (similar here & here) Pants: Levi’s 501 / Shoes: Rag & Bone / Earrings: Brinker & Eliza

Lately, I’ve been feeling the urge to write about dating. About two years ago, I put myself back out there after a break-up with someone I’d been with for a veryyy long time. At first, it was really hard for me to adjust to a lifestyle without a long-term significant other — it was a time in my life where I felt the most vulnerable. So in light of that, I wanted to round-up a few thoughts I had while I was back on that initial dating scene, and share some insight I gained from those many first dates.

First dates can be nerve wracking, so it’s always important to feel good about what you’re wearing. For me, fashion is about the way you feel, and you always want to feel confident when you’re meeting someone new. So, start by putting whatever you wore to work that day back in the closet. Remember, it’s a date, not a job interview.

My go-to first date outfit is always a pair of high-waisted Levis jeans and a fun blouse. I love peplum, floral, or patterned shirts, but go with whatever you think fits your style and personality. I also prefer my hair down, with some beach-waved curls. (GET THE BEACHWAVER IF YOU HAVEN’T ALREADY!) I love this look because it’s flirty, fun, and shows you put in a little effort, without being too done-up.  

If the date-night spot is a little fancier, I always make sure to throw on some cute spunky heels. Then I add a little liquid liner, and I’m ready to go. Hint: if you’re unsure of what the dress code is like, I think it’s always best to be a little overdressed, rather than feeling like you didn’t get the memo. At the end of the day, just make sure that whatever you wear you feel confident in, or else you’re going to be worried about aspects of your outfit all night, instead of trying to get to know your new beau.

To be honest, I've never been into dinner on the first date; I personally think it’s intimidating, especially if you’ve never met the person before (example, Hinge.) For men: My first rule is you should ALWAYS pick a place that’s casual, but still romantic and cute. Think cozy cocktails or an intimate wine bar.

For me, the first date should be more of a "looksy" — it’s all about getting a feel for their personality to see if you vibe together. For both men and women: I also suggest to have a backup activity planned, so if the date is goes well you two can keep getting to know each other after.  

Now if you’re meeting for drinks, I recommend sitting at the bar. This is for a few reasons — for starters, I think it’s less awkward and more casual, since there’s already so much pressure when you’re on that first date (which, FYI, there shouldn’t be, it’s just two people getting to know one another). But, I find it’s best to keep it low-key, even if it’s just for your own peace of mind. Also, when you sit at the bar, you’re physically closer to your date, so it’s easy to touch them on the shoulder if you like their jokes, or to tap them on the knee to show you’re interested. Body language is key people.

New York City is the perfect place for a first date — it’s a city filled with romantic bars, charming restaurants, and endless ways to get to know someone new. And remember, you should never be afraid to put yourself out there and share your time with another human being. Even if you don’t wind up on a second date, it’s important that you tried. That you made the effort.

And at the end of the day, if all else fails, at least you can say you enjoyed a nice glass of wine and some tasty food. Don’t stress about finding that perfect person, the right one will come along soon! Most likely when you least expect it.

In terms first date location, I have a few favorite city spots that that I highly recommend:


  1. The first is Dante, “where everything old, is new again.” It’s small and cozy, located in Greenwich Village, with a lot of history to it.

  2. The next is Bar Fortuna. It’s hidden away on the second floor of Casa Apicii, and as soon as I found it I fell in love. Its small, intimate atmosphere makes it an ideal place for a romantic date.

  3. I have a soft spot for Raouls. My parents went on their first date here, so it holds a special place for me. It’s a cute french bistro in SoHo, which also happens to be the home of cupid’s bow (I swear everyone who goes here on a first ends up getting married).


  4. The Freehand Hotel recently opened up in Gramercy Park, and has literally EVERYTHING you could ever want in a date! There are two restaurants, and two really fun bars all in the hotel! My favorite is Broken Shaker on the roof. Think tribal vibes.


  5. Next is The Penrose, a trendy pub on the Upper East Side. They have live music on Sunday nights, which is awesome if you want to catch some local jazz, blues or folk music.

  6. Another one of my favorite date spots is UVA, especially if you’re in the mood for some Italian food.The food is mouth-watering good. It’s one of the most loved wine bar restaurants in the city, so make sure you have a reservation instead of trying to do a walk-in.

    X kt

Other First Date Outfit Ideas Below:


Photography by Meg Niemann | @MSNPhotography