First Date Outfits (From 100 First Dates)

Following up with Lisa's post on dating in another country, I wanted to share my contribution to her killer dating site - 100 First Dates. (The name reads true - she's been on 100 first dates. Holy macerole.)

I've never had to date while living abroad, mainly because I'm married and that pretty much covers that. But it's not what you think. Being married doesn't mean I own a home, or a car, or that my hair is clean.

Here's the scoop, straight from 100 First Dates, plus ideas for great date night outfits below: 


So, here’s the thing: I’m married, and it’s not a big deal. The idea of being a “wife” and being “married” makes me feel like someone I’m not, so I tend to play it down.

I love my husband and we have what I consider to be a pretty stellar relationship, but saying that makes me sound like I’ve somehow retired from life and now spend my time taking Instagrams of my wedding ring. It’s not like that at all.

Why am I even telling you this? Because at the heart of it - to me - marriage is casual. It’s two people who really like each other and just want to be together and that’s about it. Even the way we met was (relatively) simple – through a friend of a friend. Sure, it involved a three-year long distance relationship which I won’t even get into, but let’s go back to the beginning so that I can tell you how we met and what I was wearing. Yes, it matters.

It was a Friday night. I lived in Manhattan at the time, my friends lived in Brooklyn, and there was a big group dinner in Park Slope that I wanted to do anything but attend. You know how Friday nights go – sometimes you just want to stay home and go to bed. Luckily my mom talked me out of this one, and I went to what ended up being a pretty important dinner.

Because I was so ‘meh’ about the whole thing, I wore what I wanted to wear: a pink thrifted jumpsuit with elephants on it, a blue and white cardigan, and a sparkly headband. Totally wore that, and I still wear and love the elephant jumpsuitthankyouverymuch, though nowadays the pink jumpsuit is more likely to be paired with a black blazer and some oxfords rather than a sparkly headband.

My now husband and I hit it off, flirted for a few days, and then dated long-distance for three years before we got married last year and I moved to London. To this day, he remembers what I was wearing, because it’s a reflection of who I am. He was and (um, hopefully?) still is, just fine with that.

This teaches us all a pretty valuable lesson when it comes to the dating world. Whether you’re more comfortable in jeans and a t-shirt or heels and a dress, you should wear what you want and just be casual about it. If you feel comfortable in your clothing, you’ll be comfortable on the date. That’s all there really is to it.

Here’s the long-winded point: both with your outfit and with everything else, just try to be yourself. It’s so hard, it really is, but why do you think you always hear those annoying stories about people finding their person when they weren’t looking? Because when you’re not looking, you’re not trying, and you’re just being yourself. Honestly, there’s nothing more attractive than that.


“Be yourself” not enough? Here’s some solid outfit inspiration that might help you on your next date:

For a casual day date, don’t be afraid to experiment with double denim. Pair your best

skinny jeans with abutton-down chambray shirt.


Wanna get a little fancier? Go for some boyfriend trousers in navy, a blouse or even just a nice white teeAdd some classic black heels and accessorize however you’d like.


Or, if you’re more of a dress gal, I’d recommend Madewell. Their dresses strike the perfect combo of “cute” without showing too much skin. The casual Leather-Trim Dress, Silk Drop-Pleat Dress, and the ultra-romantic Pleated Sheer-Sleeve Dress are go-tos in my book.

More styling inspiration:

date night outfits / Second Floor Flat
date night outfits / Second Floor Flat