DO THIS DON'T: Wear Sneakers With Dresses

I get so much more excited when getting all dressed up to go out now because I know I’ll be able to walk and stand and dance all night without any pain.
Publish date:
January 13, 2014
heels, Sneakers, footwear

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I own at least a dozen pairs of heels, but every time I put on a dress this past month I left my heels in the back of my closet in favor of… sneakers.

You have to understand that this is really weird for me. First of all, at 5’4” I’m the smallest person in my family. My younger siblings and my boyfriend all tower over me. I love the height heels give me.

More importantly, I have a traumatic memory of my mother forcing me to go to school in third grade wearing my prettiest dress paired with my ugly hand-me-down sneakers. WHO SCHEDULES PICTURE DAY ON THE SAME DAY AS GYM? The entire day, I was convinced that everyone was ridiculing me behind my back for my ridiculous ensemble. Sneakers with a dress just felt so WRONG.

… Until suddenly, one day it just felt so right. I’m not totally sure what happened but I suspect it was the usual business of me seeing hot people do it on the Internet and then deciding I can do it, too.

Say what you will about Kristen Stewart, the girl knows how to pull off the sneakers and fancy dress combo on the red carpet... or even on stage. Not into the surly twenties-something aesthetic? That’s OK, I also got a lot of inspiration for this look from Emerson Fry. They know how to make it look chic and grown up.

Still not convinced? Fine, but at least listen to my reasons before you stalk off in disgust and four-inch heels:

1. You can actually move and DO stuff.

Listen, you might be great at walking in heels. I know I am! Years of practice have allowed me to perfect my effortless strut. Still, there are some things I can’t do in heels (or at least not without some difficulty) because heels are by nature somewhat limiting. Running, jumping, dashing down the stairs, and traipsing around in mud and snow are all difficult to do in heels.

If you wear sneakers and a dress on your next date, you’ll still look like you made an effort but you won’t be limited by your footwear. This outfit says “I’m fun, confident, and willing to be spontaneous!”

2. You’ll learn to embrace your height.

Like I said, I’m a little on the short side so I often compensate by wearing heels. There’s nothing wrong with that -- until it becomes a crutch, like getting stuck in a rut of always wearing makeup because no one has seen your bare face. (I’m not judging; I’ve been there.)

Once I started wearing flats and sneakers more often, even to more formal occasions, I started to feel more comfortable at my natural height. The biggest and most unexpected bonus was that it encouraged me to improve my posture. When I’m not wearing heels, I suddenly feel the need to stand up as straight as possible. In the end I look and feel more confident.

3. No more pain/foot problems.

Remember when Abby broke her foot and posted about cute flats? An even better solution is sneakers because they’re more likely to give you the proper support.

I get so much more excited when getting all dressed up to go out now because I know I’ll be able to walk and stand and dance all night without any pain. I wish this had occurred to me in college, when I was one of many girls in high heels stumbling over the crumbling brick sidewalks on the way to the bars. Now THAT was the definition of pain.

4. It looks awesome.

Seriously, no matter what your personal style is, there is a way for every one of you to pull this off. It’s so customizable! You can wear your sparkly clubbing dress with your beat up Converse, or wear cute red sneakers (I got mine from Target ages ago) with a casual day dress for spending the afternoon shopping.

You could even wear a nice pair of Nikes or Keds with a classic shift dress to work if your workplace isn’t super strict about that sort of thing -- or if they are, you can at least look good and feel comfy wearing them on your commute.

In case I managed to convince you, here’s a roundup of some of the sneakers I’m currently coveting:

Going clockwise: New Balance for J. Crew, $80; Comme des Garcons Play Converse Sneakers (also available in low-top and black), $110; Chuck Taylor Low Sneakers, $45; Elizabeth and James Evva Sneakers, $275; Kate Spade New York Keds Polka Kick Sneaker, $75; and Nike Air Pegasus 83 Sneaker, $75.

So what do you guys think? Would you be willing to trade in your heels for sneakers every once in a while, or are you having flashbacks to third grade picture day?

You can follow Kelly on Twitter @picturesqueliar for more endless spiels about footwear.