Ten First Dates, Ten Outfits, One Very Honest Review
Photo: Wilfredor, CC BY-SA 4.0, via Wikimedia Commons
I did something slightly unhinged last weekend: I scrolled through ten years of first-date photos and rated every outfit like a panel of one. What I found was less a fashion history and more a diary I didn't know I was keeping. Here it is, warts and wedges included.
The Decade, Rated
1. The bodycon dress, 2015. 3/10. I was twenty-three and dressed like I thought I was supposed to look. I couldn't sit down without strategic breathing. The date was fine; I remember nothing about him and everything about shapewear.
2. The 'cool girl' flannel, 2016. 4/10. I wore a flannel to a nice restaurant because I didn't want to seem like I was trying. I was trying. Extremely. The outfit lied about me and he liked the lie, which was worse.
3. The brand-new heels, 2017. 2/10. Unworn, blister-inducing, and we walked three miles. He was lovely about it. I was not lovely in any way.
4. The all-black everything, 2018. 6/10. Genuinely good outfit, worn by a genuinely nervous person. The clothes were ahead of me.
5. The sundress and denim jacket, 2019. 8/10. First outfit that felt like me. We went to a farmers market thing in Austin and I looked like someone you'd want to share a pastry with. We shared a pastry. It didn't go further, but the outfit did its job.
6. The pandemic porch date look, 2020. 7/10 for creativity, 5/10 for execution. Nice sweater, sweatpants below frame, hand sanitizer as an accessory. He married someone else. Not the sweater's fault.
7. The 'I definitely didn't plan this' outfit, 2021. 9/10 planning, 4/10 honesty. Took ninety minutes to look undone. He never knew. But I did.
8. The red dress, 2022. 10/10. First date with someone I'd known as a friend. I wore red because I wanted to be seen as someone who takes up space. The night matched the dress. This is the one I remember as warm.
9. The safe outfit, 2023. 5/10. Blazer, jeans, zero risk, zero story. I was tired that year. The outfit was tired too. We were all tired.
10. Last spring: the honest one. 10/10. Good jeans, my actual favorite top, sneakers because I said I like sneakers. I dressed as the woman I actually am and let him meet her or not. He met her.
What a Decade of Outfits Taught Me
Every one of these looks was a guess about who I should be for two hours. The early ones were answers to a question someone else asked. The later ones were answers to a question I finally started asking: who do I want to show up as?
If there's a lesson, it's this — dress for the version of yourself you'd want to run into again. Not the most flattering one, not the most impressive one. The one you'd like. The rest is just fabric.
