Why You Should Go On A Date In That Weird Outfit

Figuring out what to wear as a first date outfit is some tough stuff. It takes a little more out of you than just picking up a pair of jeans off of the floor and deciding that you’re ready to convince someone you’re special.

My story begins on a Saturday morning with me sitting on my friend’s hardwood floor, leaning close to the standing mirror and trying to work miracles with a concealer brush. My friend Tom and I went out for what was supposed to be a dessert dinner the night before, but came home from a cocktail gravy train instead. The kind where fizzy drinks were ordered inside dark bars that required passwords and a healthy disrespect for budgets to get into. While most days I wouldn't wake up with too much regret over the slight headache behind my eyes, this morning was a little different.

I had a first date in about two hours and I looked like I had just been rescued from an underground bunker in the woods. I'm talking about level seven under-eye bags and hair sticking up at all ends. There might even have been a stray leaf in there.

But I had the promise of nutella pancakes and mimosas right around the corner — not to mention the possibility of spending some time with a really sweet guy — so I dipped into my pots and tubes with determination. By God, I would look human again.

As I was buffing away the hangover, my friend sat down next to me and asked the one dreaded question that comes with a pre-date package: "What are you going to wear?"

Ugh. What a loaded question. First date outfits are the worst. While some folks might just toss on a sweater and call it a day — and I envy you levelheaded people — the rest of us usually feel like there's a lot of stock held in that one outfit choice. It not only gives your date a glimpse of your personality — like taking a quick peek behind the curtain at opening night — but it also helps you build a story. It not only shows who you are, but who you want to be.

So what was I going to wear? I tapped my foundation brush on my chin as I thought about it. "I brought two options," I said, reaching over and plucking a coffee cup out of his hand. "Help me choose?"

The common denominator was white tapered pants, and I had to choose between a white bell-shaped tank or a split-side bohemian tunic in rich colors. In the former, I looked like summer dressed in all-white. In the latter, I looked like I might drape a shawl over my head and go exploring the bazaars out in the humid and spice-heady streets.

I was in love with both options.

At a loss, I asked what my friend thought, and what he said stuck me as one of those life moments: The ones when the minutes slow down a fraction, just long enough for your brain to snap them up and file them carefully away underneath a floorboard for safe keeping. He said, "It’s always best to go with something normal on the first date — you don't want to scare them away with the crazy from the beginning. You have to ease them into it; go with the white shirt."

So I went with the crazy tunic.

Why? Because right after he said it, I instantly thought, “But I like my weird self.” And I do — with all my questionable wardrobe choices, all the old lady kaftans, the barefoot-hippie tent dresses, and the high-waisted grandpa shorts. While I’m sure there have been moments when someone has seen me standing outside a restaurant from their cab and wrinkled their nose, that’s perfectly alright with me.

So if I walk into this sunny little brunch place and the guy waiting for me at the bar feels a little ill over my button-up, well, chances are he’d feel the same over my other eccentricities. What if he found out I had a whole closet of vintage coats I never wear, but love to visit and try on from time to time? He’d think I was Little Edie from Grey Gardens and dub me nuts. Or what if he found out I used to doodle “Marilyn Crane” on the margins of my notebooks because I really, really wanted to be Niles Crane’s lady love? As in, Frasier’s shy, neurotic brother. And by “used to,” I mean I still do.

We all have quirks that run louder than any pattern or questionable shirt choice. Some of us just choose not to hide them because, well, for better or for worse, that’s who we are.

I went with my crazy tunic because I felt like I’d be lying if I toned it down a notch just so the boy with the brown eyes and sweet smile would give me a chance. It felt wrong to dilute myself — to hide — just so I could have an easier go at things. So I swept my hair up into a bun, rolled the cuffs of my button-up, and stepped out into the Chicago streets looking like I might sell someone amber stones and bags of heady teas if they only asked me.

And the cool thing was, I got asked for a second date right before the first Nutella pancake was put in front of me. Because sometimes you can be someone’s cup of tea just as you are.

Images: Marlen Komar