Dress-down days are about as common as a stat holiday and nearly as well-received. For most people, they are a boon to morale. For me, they are a bane to an otherwise delightful day.

I wasn’t always like this. Once upon a time, I enjoyed Casual Friday. Twenty-twenty had its effect on us all, but for me the years that followed mattered even more—the recovery zone. I don’t think the same anymore. Every choice is placed gingerly on a scale in my mind, counterbalanced by inner peace. I have been dismantling my own autopilot ever since.

When I had to switch into my new career path, my jobbing autopilot was activated and ready. Fill out forms. Pay staff fees. Throw together my best working wardrobe. I’d already run into my first issue. See, my old work clothes, of which I had many, were of a different industry. One where scrubs were the norm. My new job was at a local high school working as an Education Associate. My budget for new clothes: non-existent.

My tops weren’t terrible and I had a couple other dress shirts and t-shirts to interchange. But wearing the scrub pants with the scrub shirts was not an attractive option. It would draw way too much attention. I already felt self-conscious when I had to wear the tops. So, for most of the days, I was wearing jeans with everything.

As it goes in new jobs, I was learning as I went. I discovered that jeans were not considered acceptable for daily wear and were only acceptable on days that were granted as “dress-down” days. I stayed my course. The principal had said nothing so far and I figured I could at least claim ignorance until then. If she did say something, I would tell her about my predicament and buy myself some more time. And then something unexpected happened.

I was having a casual conversation with a coworker when she said to me, “How has no one talked to you about wearing jeans?”

It didn’t feel curious, it felt pointed and I sensed her disapproval. I chose my words carefully to give her something to chew on, rather than answer the question: “I don’t know, I’m just glad I don’t have to have the awkward conversation about how I don’t have anything else right now.”

The look on her face told me that I had made my point well and she dropped it like it was hot. However, I didn’t stop thinking about how my superior had said nothing, while my peer made it her business. Even if my boss simply hadn’t noticed, the social implications remained the same.

This experience has stuck with me and been a catalyst for deeper reflection. What compelled her to comment on my wardrobe? Was she hoping to gain my compliance or something else, perhaps? I began to wonder how often social systems surreptitiously compel our conformity to rules that, when examined, reveal themselves to be largely arbitrary—maintained through subtle pressure that keeps everyone quietly yielding.

It didn’t matter though. I had to live my reality. I continued to wear jeans until I could afford to buy new clothes. I was not deeply bothered by what she had said, but I was impacted nonetheless. With her words resonating in my mind, I was entertained by countless imaginary counter-arguments. What is wrong with my jeans? Do you know how much I paid for these? Have you seen what the high-schoolers are wearing? At least mine don’t have rips in them. Though she was critiquing my ability to fit in with social expectations, I had discovered something unforeseen. I was unpacking a deeper inner misalignment.

Over the next while, I learned a fun fact. It turns out that the “staff fees” I had unquestioningly paid were largely misrepresented. A more accurate name for this “fee” would be a “dress-down donation,” since only ten dollars went toward actual staff costs while the remaining fifty funded dress-down days. It’s a curious feeling, paying for the privilege to wear something I had felt shamed for wearing. Even more curious is the paradox of mandatory philanthropy and casualness.

Working in a school is interesting. A clearly defined cycle with much opportunity for growth and reflection. That is the environment, the substrate. In year one, I had paid the fees without question. In year two, after much deliberation, I made a conscientious objection. I don’t have extra resources. I have made intentional sacrifices to live with integrity. My family comes first. Fitting in does not qualify as a good reason to do anything. I am willing to forgo the social benefits of this offering, though there are still some days where it feels like a hard hill to die on.

But for a moment, let’s just assume I could afford it and money was no object. Would that alleviate my angst? No, it would not. And here is why.

Jeans were invented as a solution to the rigorous demands of manual labour. When they became popular with the youth, the schools and offices responded with scorn saying these durable garments were inappropriate and unprofessional ‘blue-collar’ garb. When workplaces eventually adopted them into dress codes, it was arguably less about employee autonomy and more about organizational gain. Morale, corporate culture, and productivity were boosted, offering little tangible advantage to the people wearing them. Since the 1970s, jeans have found their place on the fashion runway, making them often more expensive than standard dress pants. Meanwhile, nobody bats an eye at other visibly casual garments.

So please forgive me if I don’t get excited when I am told what to wear, asked to pay for the privilege of wearing it and expected to be grateful for the opportunity. Naturally, the system will continue to prod my compliance with threats of lost house points and other subtle social consequences tucked neatly at the end of weekly staff newsletters.

I will continue to wait for the true bill.

The school has a lot of spirit days and I always try to participate, when I am able, to gain house points for my team. I am signed up for text notifications so that I don’t miss out on these. From the same source comes the notices about dress-down days, which I have learned to ignore. These are not for me. I have not paid for this privilege.

I do not recognize dress-down day as a reward I enjoy receiving, nor am I obligated to corporate pseudo-community — aka adult peer pressure. Furthermore, this position allows me to exercise clear judgment on the boundaries between professional and unprofessional, choosing what aligns with my work and values rather than following the unspoken rules of social expectation.

I have a raise coming soon. If I can afford the “fee,” I’m not sure that I’ll pay. This resistance does neither have to be futile nor fighty. It can just be.

Twenty-twenty was a gift. A gift that allowed me to see how quickly life makes its offers and how often my agreement is tacit through my reflexive participation. These days, when I take a moment to stop and look at what is being offered to me, I am surprised at how often I decline things I previously accepted at face value.

Nowadays, I mostly wear cargo pants—far more casual than jeans—yet miraculously, they pass the stylistic threshold without remark. And every once in a while, I wear my jeans when I feel like it—because I am a grown adult capable of dressing myself appropriately for work.