How My First Date Uniform Taught Me To Be Myself

Lessons in life and love, via one pair of excellent overalls.
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Photo: JD Hancock

Photo: JD Hancock

Over the past 12 months, I've gone on approximately 10 first dates with (more or less) complete strangers through the matchmaking powers of eager friends, dating apps and in one bizarre case, the New York Post*. And each time, I wore the exact same outfit: black skinny overalls, a white T-shirt and white sneakers. Listen, I know you've probably read a thousand personal essays about both dating and uniform dressing, but the Venn diagram space where those two clichéd spheres intersect is worth a closer look — I promise. Bear with me. I'm just a girl, standing in front of the Internet, asking it to hear me out. 

Before we get to the clothes, let's talk a bit about how I approach finding millennial companions. I think Heather Havrilesky, aka "Ask Polly," said it best when she described relationships in your 20s as "boarding one of those ridiculous Second World War bomber planes" and flying it perilously across the Pacific Ocean. Following this analogy, I have racked up many frequent flier miles on The Way We Almost Were Airlines, where you always have to pay extra for baggage and no one helps anybody else with his or her oxygen mask. Havrilesky continues: "You board the plane, all hopeful and excited, with raw, brilliant emotions and desires of your own swirling round inside of you, and the second you make a tiny squeak about what you want, that shit falls out of the sky, straight into the sea." I can verify that this is frequently correct. 

There's not much I can personally do to change the reality that many people in their 20s and 30s don't know what they want, don't know themselves and will jump out the window the second that plane engine makes the slightest cough. What I can do, however, is try to be more efficient with my time and emotions by presenting the truest version of myself from day one. This is not my natural instinct. I want to be the Cool Girl — you know, the hot and understanding one that doesn't mind if you don't ask me any questions for three straight hours. But if I perform the role of the Cool Girl for several weeks and then said millennial companion flings himself from the cockpit when I finally let slip that I am a community of loosely held organs controlled by impulsive and paranoid hormones, then I've wasted everyone's time. Chiefly, my own.

When I dived head first into the dating world a year ago — after being forcefully ejected from a longish relationship — I was at a loss about what to wear on proper first dates. A dress can feel too ladylike; skinny jeans too basic; boyfriend jeans too frumpy; shorts too revealing, etc. And, worst of all, none of those felt like an accurate representation of me — whoever that is. 

This is where the overalls come in. In December 2014, I bought a pair of Frame skinny black denim overalls during the Net-a-Porter holiday sale. Sure, I was late to the overalls trend, but I didn't care. As soon as they arrived and I put them on, I instantly felt like the best version of myself. They are basically a tight, stretchy body sock that make me feel thinner and taller by virtue of the dark wash and high-waisted silhouette. I started wearing them about two days a week, and they quickly became a staple — a personal signature among my friends and coworkers. They struck the perfect balance of considered yet casual, girlish yet sleek, quirky yet basic.

The overalls should have been an obvious first-date choice (I'm certainly not the first person to date in them) that I initially discounted because I worried they made too much of a statement. The Cool Girl doesn't make strong statements, said a voice inside of me. How will I present myself as the perfect reflection of what he's looking for if I'm wearing fucking overalls!? 

A second painful rejection ultimately freed me from that line of thinking, and I made a promise to myself to wear my favorite overalls on every first date for the rest of my tragically unattached life. And then something magical happened: Not only did removing outfit options take a weight off my shoulders, but the overalls also served as an excellent litmus test for boys. It's a conversation starter every time ("I can't believe you're wearing overalls on our date!"), but more importantly, the comfort of my tried and tested pair empowered me to be unapologetically myself — a goofy, anxious, salty, cranky, practical, defensive, flirty person. A person I understand better each time someone decides he doesn't want to know her anymore. 

Once, I frantically ran my overalls to a tailor after I busted the long side zipper in the middle of a "first drink" (it was embarrassing but ultimately endearing). I had another first date two days later and was panicked at the thought of having to figure out something else to wear. That dependency didn't feel good. I wore them on several more first dates, but soon, the magic started to fade. 

My overalls were a perfect dating security blanket. But as with all comfort objects, I outgrew the need. On one early summer day, I decided I shouldn't rely on this pact with myself any longer. The first dates I go on are still full of snap-judgements and self-description, but I don't want my clothing to do the heavy lifting for me — my own voice says more than a bib with buckles ever could.  

I've learned that despite how scary it can feel, I'll save myself some heartache by playing the role of me and accepting the outcome without regret. Meanwhile, my overalls still hang in the closet, zipper repaired, as a physical reminder that despite all the false starts, I'm still my own best bet. 

*If you're curious about the aforementioned New York Post blind date, you can read all about it right here.

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