Written by: Charlotte
Elementary school was when I began to make my own outfit choices. There is a legendary photo of me from my first-grade picture day that I believe perfectly sums up my ideas of fashion from age 5 to 22 (see below).

As you can see, I have paired a horizontally-striped turtleneck t-shirt with vertically striped shorter-alls (for those of you unfamiliar, this means overalls that have shorts at the bottom instead of pants) both in the same orange-yellow color family. On top of this glamorous foundation, I threw on a purple zip-up patterned with snowflakes. Let me now articulate that it was early September and probably somewhere around 85 degrees — a perfect time to remind everyone of the snowflakey winter ahead as represented by this iconic cardigan. To tie the entire outfit together, I stuck a gigantic orange puffy sticker with a jack-o-lantern on it in the middle of my chest (you can see it peeking out of the shorter-alls). I specifically remember receiving this sticker at the dentist at an appropriate Halloween-adjacent time and saving it for the perfect day. Picture day was my moment. I proudly peeled it off my dresser where I had been storing it and transferred it onto my person, completing this show-stopping number. I can only imagine what the photographer thought of this toothless pumpkin-child. I can only hope I spiced up his day of photographing hundreds of children with combed hair and button-down shirts.

To me, fashion was about being comfortable and vaguely-coordinated (i.e. wearing two different kinds of stripes that were both orange-ish). Comfort, for me, meant clothing that I would not feel restricted in when running around at recess. I needed to be able to transition from rolling down the dirt hill to flipping off the monkey bars without having to worry about my underwear showing. Therefore, my wardrobe consisted exclusively of overall-style items, leggings and that was it. I did not own a real pair of jeans until I was at least 12 and even then I insisted on the extra-stretch kind just in case I needed to perform a cartwheel at a moment’s notice.

I waltzed into college with this same philosophy. I so badly wanted to be the cool girl who would be your spotter at the gym but who would also look great in a candle-lit restaurant. But I could not, for the life of me, put the two together. I wore sweatpants and sweatshirts to class for the entirety of my freshman and sophomore years of college. I could not understand why people were getting dressed up and putting makeup on in order to talk through “The Yellow Wallpaper” for the ninth time. I figured, I’m going to be sitting in an windowless basement trying to sound smarter than the person next to me, I cannot also be stressed about whether or not my belt was going to do that thing where it rises above your belt-loops giving your neighbors a nice view of the only belt you own (which was made out of a rope-like material), your not-sexy underwear and your jeans hanging onto the top of your butt for dear life.

Not until I began teaching did I realize that dressing up is a form of respect for yourself and for those around you — namely in professional settings. Showing up to class in an outfit that one of your students said reminded him of “Indiana Jones and not in a good way,” conveys a sense of carelessness that other people will pick up on. Caring about your own appearance, I learned, lets other people know that you showed up to work today rather than to go on a spelunking expedition.

Though I still wear leggings more often than not and maintain a personal wrath against button-down shirts (are they uncomfortable to all women or do I have the body-frame of a linebacker?), I understand that sometimes you just suck it up and sit through a meeting in a blazer that restricts your arm movement to the point where you can only take notes on the bottom-half of your paper. I will always remain in contact with my inner-sweat-pant-clad self (in fact at this very moment I am wearing a onesie made entirely out of sweatshirt material), but I will simultaneously channel Michelle Obama because that woman could not possibly be 100% comfortable 100% of the time while looking like a runway model and also queen of the universe.

Major Takeaways:

  1. Comfort is king, but once you turn into a real-life adult you should probably think twice before leaving the house in the sweatpants you got from your high school field hockey team.
  2. Fashion is about embracing your own style while remaining conscious of the fact that sometimes your professional environment does not always call for your “professional” tuxedo t-shirt.
  3. Jack-O-Lantern stickers are never not on trend.