Dating as a Fashion Girl, or How I Re-Learned to Get Dressed in the Morning

In trying to find a dude, I have found myself. #deep
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Tyler McCall
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In trying to find a dude, I have found myself. #deep
Here I am, world. Date me. Photo: Nina Frazier Hansen/Fashionista

Here I am, world. Date me. Photo: Nina Frazier Hansen/Fashionista

Monday, while I was pitching this story, Eliza looked at me and asked, "Are you going on a date tonight? That's a very date-y outfit."

I wasn't, but it was a fair question: I had put on a gray tank top and a tight black pencil skirt that I hadn't worn since winter. Last Friday, I put on a pair of pants and realized it was the first I'd worn in over a month. 

That's because, after my long-term relationship ended last fall, leading into a dating sabbatical to find my inner Beyoncé, I jumped back into the dating pool at the beginning of summer. And the first hard lesson I learned, when a guy I met on Tinder took my gentle suggestion to "grab drinks sometime" to mean "in an hour, after work" was this: You Must Always Be Ready for a Date.

You see, that day I had chosen to wear my "grandma chic" shorts. Which are cute! But not very guy friendly. My date, wearing a suit fresh out of work, looked at me a bit confused. Now, it's not like I dress at Man Repeller levels of fashion daringness, but up until then, it had been a very long time since I'd had to think about what a guy thought about what I wore

I'm not trying to change myself -- I have a basic allergic reaction to anything body-con and I refuse to wear heels because I just can't be bothered. Still, I've made some basic tweaks when getting dressed in the morning. 

First, more skirts and dresses have made the rotation. If I know I have a date, I wear the Banana Republic dress shown above, in black or the navy stripe, because it's pretty but also not super in your face. (I promise I'm not trying to brag here, but my boobs get enough attention without being out.) I've also had pretty decent success with my floral tunic dress. Other pieces have gotten mixed results; one date looked at my faux-leather shorts and bemusedly remarked that I must be pretty committed to fashion to wear leather in the summer. And then there's the musician who remarked he liked my Peter Pan collars, which made me want to buy one in every color. (Don't look at me like that. He's super cute.)

That's to say nothing of my beauty routine. Gone are the days of skipping shaving or a messy bun. I take better care of my nails and I've stopped wearing bright red lipstick (except on a second date with a guy I didn't want to kiss me). I even started wearing -- wait for it -- lip gloss. I know. I don't even know myself anymore.

And we haven't even touched on lingerie! Nor will we, because I am a lady... also because my parents read this site. Hi, Mom and Dad.

It might sound like this is a bad thing, that I'm somehow giving up part of my identity to find a boy, but it's not! It has made me a more considered dresser and thus I feel more polished and put together -- I don't remember the last time I threw on a shirt and my baggy destroyed jeans. So regardless of whether I have a date lined up for that evening, I walk around with more confidence, and that has to be good all around.

At any rate, I'm really hopeful that I have a boyfriend by winter -- not because I can't handle being single anymore, but because when it gets cold, I retreat into a steady, non-date friendly wardrobe of skinny black jeans and fashion-y sweatshirts, plus lots and lots of red lipstick.

Gentlemen, the line forms to your right.