that time when I wore overalls every day in july
might i add: during record-high temps
Welcome to Congrats, You Played Yourself, a newsletter about growing up and celebrating the mistakes made along the way.
I share stupid stories about myself, my pets, friends, strangers, twitter friends, and anyone else who’s willing to share. I’m always looking for more stories to join my own so they aren’t embarrassing and lonely — they’re embarrassing with friends. If you’re willing and able, hit me up. If you like this post, give it a share or a heart. Life is dumb, and that’s the best part about it.
Last July, I accidentally wore a pair of overalls three days in a row.
Well, not accidentally, necessarily — actually, quite on purpose. I had just gotten this new pair of overalls. A gloriously comfortable, deliciously soft, perfectly blue pair of overalls. I had seen an associate at Aritzia wearing the perfect blue overalls with a cute green crop top, so, naturally, I bought her exact outfit.
I wore them immediately. I did not care that it was 93 degrees in the high desert of Yakima. This was July 3rd. Then, because almost nothing feels more patriotic than a pair of overalls on the 4th of July, I wore them on the 4th of July.
July 5th, I had a three-hour trek back to Portland. And almost nothing sounded better than a long drive in my comfiest pair of overalls.
July 6th, having realized I had now worn the same pair of overalls three days in a row, I channeled our Lordt and Savior Hilary Duff and asked myself, “Why not?” And then I asked the good people of Instagram for their thoughts.
So, I committed to wearing the overalls the rest of the month of July.
And then Oregon had its fourth-hottest July on record.
As a former Catholic school student, I thrive off of predetermined dress codes and spent a majority of ages 8-18 in a committed relationship to Abercrombie & Fitch polos and khakis. Save for a few rare days when my chemistry teacher called me out for wearing a t-shirt secretly under my sweatshirt, I never deviated from the absolute slam dunk that was a polo+khaki combo.
When I hit college and had to fend for myself — ie: there was no one telling me what to wear every day anymore — I became infamous for dressing like an athlete even though I wasn’t one because I refused to wear real pants and instead opted for basketball shorts every day. One of the only (I like to think) giveaways that I was not a student athlete? I paired those basketball shorts with Ugg boots. Thus, a sartorial legend was born.
Or at least, a lazy sartorial legend, aka: one who was looking for the path of least resistance when it came to dressing oneself, aka: a uniform.
After college, turns out it’s not “appropriate” or “professional” to wear basketball shorts and Uggs to your real adult job. So I abided by the rules of the corporate world and started wearing pants — and sometimes even dresses!! — to conform to the necessary work dress code in order to avoid getting fired, or worse: written up by HR.
I was fired anyways (read: “let go”) (not because of what I was wearing lol) and eventually made the move to work at Nike, where wearing basketball shorts wasn’t a red flag but a green one. I had already made a habit out of putting pants on everyday, so I adjusted to a new mini dress code of daily Air Force 1s. Wearing the same pair of shoes every day became one less thing for me to worry about in the morning, freeing up my brain space for much more important things like royal family drama and TikTok binges and the entire four years that were 2016-2020. The AF1s quickly became part of my identity, much like the basketball shorts and Uggs once were.
Which brings us to July 2022, and my general willingness to embrace a uniform lifestyle.
It started as a simple decision born out of one part laziness, one part challenge, and one part self-imposed social pressure.
I thought I would thrive! I would be the next Steve Jobs! Or at least the next Elizabeth Holmes without the whole modern-con-man element but probably just as eclectic!
Narrator: she did not. She was not. She definitely was not.
Looking back, I was obviously dramatic. (Insert here: “is it me? am i the drama?” tiktok) But by day 9, I was ready to give up. It was hot. I was bored. My overalls already had seen too much.
Did I mention it was really hot in Oregon?
Nevertheless: she persisted. Through what? Let me count the ways:
28 out of 31 days of July
4 separate outfit repeats
3 different states
3 triple-digit temperature days in Portland
2 nieces’ birthday parties
1 bachelorette party
1 93 degree day in Yakima
1 extremely bad case of hangxiety
1 WNBA All-Star Game
Internally, I didn’t learn anything life-changing: a few realizations here and there about how much farther I can take my wardrobe, a couple creative breakthroughs related to layering and strap strategy, how much slower I eat when I am under pressure to wear the exact same overalls the next day and do not have time to do laundry if I spill syrup onto aforementioned overalls.
Most importantly though, it was fun. It was annoying sometimes, yes, to lie in the bed that I, myself, had made — but ultimately, fun. A little challenge to spice up the day to day. A little talking point to update folks who cared and to confuse the ones who did not. Not to mention, a little stinky at the end of a month of wearing the same piece of clothing nearly daily.
And externally: listen, did I change the world wearing my overalls nearly every day of July 2022? Absolutely not. At the most, I gave these overalls something to write home about, my boyfriend an arch nemesis in the form of denim, and my Instagram followers a mini-diatribe about fast fashion on my last day that was not planned but gave an interesting socio-political commentary twist to my overalls challenge.
And now, this April 2023, I’m back at it again. I’m already learning from my mistakes I made before: I’ve specifically chosen a month more conducive to overalls wearability on the comfortability scale, and polled IG folks at the beginning of the month on what fun adventures I should take these bad bois on. We’ve got 21 more days of action ahead — let’s see where these overalls can take me.
What’s your favorite article of clothing, and would you wear it every day for a month? Why or why not? Give it to me in the comments.