I Tried 7 Different Date Ready Outfits, And Here's How I Felt While Out On The Town In Each Of Them

First dates are no easy ordeal. Getting ready for a first date is even messier. Where most guys just put on deodorant and run a testing hand through their hair, girls have more of a, let's say, ritual around the whole event. It usually includes a couple of hours of primping, curling, straightening and painting. And peppered through the whole thing are glasses of wine, deep breaths, excited smiles and second guesses.

I don't know about you, but by the time I end up in front of my closet with a towel on my head, I start wishing I wasn't so social and just had an evening of Netflix and Easter candy planned. It's just the butterflies talking, but I always have this small moment of wild panic where I look around my room and start thinking of escape routes. Maybe I could say I have a lot of homework and I can't come out? Wait, he knows I'm not in school. Or I can call and say I'm coming down with a cold? I heard if you hang upside down from the edge of your bed your voice will sound congested. Okay, calm down, Mar. Where's that glass of wine?

After I get my crazy out of the way, the real fun begins: The choosing of the outfit! What you wear will set you up for how you'll feel for the rest of the night. Choose something you feel like a total fox in, and you'll act like said babe throughout the evening. But choose something you feel fidgety and not like yourself in, and you might be more concerned with how your cardigan is sitting rather than how smitten your companion looks every time he/she glances your way. It can be a tricky balance between wearing something that's all you, and wearing something that personifies the type of you that you want to portray. Below, I tried on seven different date-ready outfits, and tested how differently I felt in each of them. Some of the outcomes were surprising, some were hilarious, and some fit just right:

The Statement Piece Outfit

Confession time: I'm no stranger to wearing ballsy outfits. I like to wear 50s inspired vintage with red lips and pillbox hats, and have worn sweeping evening dresses with knit sweaters more than once to the grocery store. But there's something about wearing a statement piece on the first date that makes me shrink inside slightly. It's a little too "tadaaa" for me, where I begin to think more about what he thinks about my look and whether he's digging it or not.

While you see amazing dresses and killer heels as first-date wear in movies, I'd probably be squirming all through drinks and wishing I was at home watching The Daily Show with a cup of tea. I felt like the date became more about the skirt and less about us. It completely third-wheeled the whole shenanigan!

The Trendy Piece Outfit

Or as I like to think of it, "The On Point Outfit." And as he likes to think of it, "The Man Repeller Outfit." You should have seen me blow into the bar with this look. I was all:

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Girls left and right gave me the once over and then nodded their heads in approval before going back to their drinks. I felt amazing. And he... well, he ran a testing hand down the fur and then smiled in that confused, tight lipped way boys do every time a female does something mystifying in front of them. Like curl her eyelashes with something that looks like a Medieval torturing device, or, you know, when she channels her inner Viking warrior. This was a total go for me, and a total no-go for him.

The Cozy Outfit

You know how most of us take the "let's kill him with this dress" route when planning for the first date? Well, what if you forewent the tight dress and went the opposite direction? Say, with cozy and baggy layers instead?

For this date I decided to dress how I would for lunch with my girlfriends: Wearing a sweet midi skirt and a cozy turtleneck sweater. I felt adorable and completely like myself... but some of my pluck disappeared within those layers. I was charming and flirty, but maybe a bit more subdued. I felt more American sweetheart and girl next door, and acted hand in hand with the feeling. A few times I'd have something witty and sharp to respond back with, and it almost felt... out of character. It seems like that killer dress does play a role on that first date: It lets you test out a new temperament for a couple of hours, allowing you to hide behind the slightly-tweaked version of yourself.

The Classic Outfit

This is probably the look I got the most compliments on... and also the look I was most bored in. It was pretty and quietly elegant and let me feel completely comfortable as I tried my best not to swing side to side on my bar stool, but it also felt like it lacked something. While I had chemistry with the boy, I didn't have chemistry with the look. I felt like I was out for brunch with a friend, rather than at a chic bar in downtown Chicago, being wooed by a handsome man with a sweet smile. Simple can work, but sometimes it can drag you down when you want to make an ordeal out of the evening.

The Boyish Outfit

Interestingly enough, I felt incredibly gorgeous in this menswear inspired look. I think it was because of the way the feminine and manly elements combined to create this. I wore boyish suspenders, but with a loose, low-cut top. I put on high waisted trousers, but my hair was messy and tousled. Sweetness mixed with roughness; soft curves were set against hard lines. The outcome was super appealing, and I felt bold and like I had a Katharine Hepburn-esque type of straightforwardness and frankness.

It had to be the pants. She became my spirit animal through them.

The Overly Feminine Outfit

Then, on the flip side, I tried on a look that was all lady-like and prim. It embodied white gloves and crustless cucumber sandwiches, and perfume that hinted at meadows and white dresses. I felt very delicate and female, and it made me act a little more flirty than usual. It's like the florals and pastels emboldened me to act every inch the lady I portrayed: I was all gentle arm touches and underneath-the-eyelashes glances. He was smitten, I was smitten, the bartender was smitten... this outfit did me proud.

The "Dressing For Me" Outfit

While dressing for first dates could be a fun time to play with different versions of ourselves, there are times when you don't want to be anybody else but your wonderful self. Sometimes I want to channel my inner Doris Day and be all lady-like charm while sipping on Manhattans, and other times I want to walk in through that door and have him forget his name because of that killer dress I'm wearing. Sometimes I want to be aware of my female charms and act like Sophia Loren with my slow moving smiles and crossed legs, but other times I just want to be... me. Short haired, quiet eyed, backpack-wearing me.

And the best way to show that that's me is to put on a long 90s dress, knot a shirt at its hem, throw a book into my backpack for the train ride to the bar, and be on my way. Because even though it's fun to dress up for boys and for other girls, the funnest is to see someone light up over the most real version of yourself.

Images: Author's Own; Giphy