Style Footwear Sneakers

Why I Always Wear Sneakers on a First Date

Allie Flinn

November 13, 2018

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In my experience, first dates are kind of like pilot episodes of TV shows. Sometimes you get a Stranger Things and you immediately know you're gonna be binge-watching; sometimes you get more of a slow-build Mindhunter that takes a few episodes (read: dates) to really get into; most times, though, you get something like I Want to Marry Harry and you know within 30 seconds that, no, this is not going to work. As someone who recently re-entered the dating world, it is what I would classify as a lot.

But, unfortunately, first dates are kind of inevitable if you're looking for a relationship (even a casual one). Deciding what to wear on said first date is a particularly stressful sartorial challenge. Through a bit of trial-and-error, I've concluded that no matter your outfit, sneakers are the perfect footwear choice.

I came upon this realization—nay, epiphany—earlier in the year while prepping for one of my very first Bumble dates. Here's a little mise en scene for the date: We were going to a cool, dimly lit bar in Venice. I picked out a flirty little dress that was both comfortable and flattering. But every shoe I paired with it just felt off. Not to be dramatic (but definitely to be dramatic), I would rather give up cheese for six months than wear heels on a first date. I think making awkward small talk while being strapped into painful shoes is actually one of Dante's circles of hell. Neither sandals nor boots felt right either.

I think making awkward small talk while being strapped into painful shoes is actually one of Dante’s circles of hell.

And then, I saw them: my Vans, inconspicuously sitting by the front door where I had kicked them off earlier in the day. I put them on, looked in the mirror, and heaved a sigh of relief and wonder. I imagine it was similar to how Michelangelo felt after finishing the Sistine Chapel. I looked like myself in sneakers. All the other shoes made me feel like I was trying to be someone I wasn't.

You can wear sneakers with anything, and on basically any first date-night occurrence. I'm partial to a uniform of sneakers and a dress—sneakers help tone down its fanciness without looking sloppy. They say, I'm cool, I'm chill, I definitely didn't stalk your Instagram right before this. (Related: It's just called due diligence.) Sneakers and well-fitting jeans is also a no-brainer—just throw on a slinky sweater, camisole, or button up and you're at once put-together and low-key. An iteration of these outfits works for drink dates, dinner dates, coffee dates, and everything in between. Plus, I think there's something kind of sexy about the juxtaposition of feminine clothing and sporty sneakers.

And the best part about all of this: Sneakers are so freaking comfortable. Right now, I fluctuate between my classic Vans, these black APL beauties, and, if I'm feeling a little bold, these Reebok Aztreks. Without fail, I get compliments on my outfit every time. The real beauty, though, is that I feel confident in myself and my appearance. (And, again, my feet are super comfy. Have I mentioned that?)

Required reading for every sneaker-lover: how to wash them so they look brand new, plus 10 designer sneakers you need in your closet ASAP.