The Absolute Horror That Is Dressing for Work; or, How to Navigate Dress Codes

I’ve been spending a lot of time thinking about how I dress lately, which I think is something that happens to you when you’re in your early twenties and trying to figure out how to be a “professional”. I think dress codes were always sort of a sticking point for many people, but from what I understand, in the pre-covid era there were many workplaces with very strong implicit or explicit dress codes that (I am told) made it very easy, or at the very least, easier to understand how you were supposed to dress.

Unfortunately, I came of adulthood during covid, so I never experienced this. My first real internship was remote, my second job was in a casual workplace, and now that we’re back in person (or really, “engaging in hybrid modes of work”), I’ve spent the last two years trying to navigate the new quagmire that is dressing for an office job. It’s almost like there are two dress codes: one for when you’re remotely participating in meetings, and one for when you come into the building, and the dress code for remote meetings is even more nebulous than the rest, because of course, nothing is ever easy.

I don’t know which is worse: places that say they have a dress code (that no one really understands), or places that don’t even pretend to have a concrete dress code and leave employees to their own devices. For example, lots of places will claim that their dress code is “business casual”. The problem I have with this is that there is no meaningful notion of what “business casual” actually means, only “what people wear in my office”, which may wildly differ from person to person.

Here’s a likely scenario: you spend days reading “what is business casual attire” articles, which are just as confused as you are but won’t admit it because they’re trying to be authoritative sources. You walk in wearing a blazer over a dress shirt tucked into dark pants, but you end up pairing that with sneakers because that’s what you own. You immediately feel overdressed because no one seems to wear tailored jackets around here. It seems like most of the guys are wearing dress shirts or polos with chinos, there’s that one guy wearing a tracksuit, and there are so few women that it’s impossible to tell what they’re supposed to wear. Meanwhile, your boss is wearing a t-shirt, his boss is wearing a suit, and your mind is twisting into knots trying to figure out whether it’s okay to wear t-shirts here (or whether your boss just gets leeway thanks to seniority) and whether senior management actually dress more formally (or whether the director just comes from an era when wearing suits was a thing people did).

But hey, somehow you actually got the shoes right. That was definitely on purpose. Yup.

That scenario was completely made up, but I swear, I’ve seen versions of it happen.

Last summer was my first time working in a real office, and I was feeling quite overwhelmed by this whole “dressing for work” thing. I asked two of my coworkers what the dress code was, to which they replied that there was no dress code, only “dress for your day”. “Dress for your day” is part of the annoying subset of life advice that is pithy and easy to repeat but difficult to understand unless someone explains it to you.

Of course, anyone who tells you that there isn’t a dress code is lying. Just because the way people dress in your workplace is guided by a set of softly-coded non-explicit social norms rather than any real rules doesn’t mean majorly screwing it up can’t ruin your life, and minorly screwing it up can’t affect your chances of getting promoted. As much as I hate it, impressions matter, and trying to decode unwritten rules isn’t just a thing we do for fun, it’s in our best interests.

There is a benefit to having less stringent rules around dress, I guess; in some ways it alleviates pressure to meet the standard at all costs, and hence, risk doing it wrong. The reason why I own any formal shoes at all is because I did Model UN in high school. In case you don’t know what Model UN is, at the high school level it’s quite literally teenage public policy nerds in suits roleplaying as world leaders. Standard MUN conference attire is business formal - this means suits, blazers, ties, etc. I dressed more formally for MUN conferences than I ever do for work; however, this also meant that I had to own a set of formal clothes. I did MUN for four years, so I ended up buying a collection of blazers, pants, blouses and shoes that I could wear to conferences, but most teenagers don’t really own formal clothes, which can be… awkward.

The problem with formal business attire is that it doesn’t leave quite as much room for personal expression; also, it’s very easy to get wrong. It can be expensive, and its fit and quality are something you develop an eye for over time. You could sometimes immediately tell who the new delegates at conferences were, because the way they dressed was just a little bit… off. Their shirts might be too tight, or they might show up in black jeans rather than dress pants, or their skirts might be too casual, or their blazers might be a few sizes too big. This was probably not their fault (and there’s a whole other conversation to be had about classism in MUN access), but the point is that enforcing stricter dress codes caused these sorts of problems. Being slightly underdressed, but with clothes that fit well, is always better than wearing a suit that doesn’t fit. And of course, learning that during a real job is probably… not ideal.

Last year, during the same period when I was struggling to figure out how to dress for work, I opened my closet and had the unsettling realization that I hadn’t properly shopped for clothes since middle school. It wasn’t just a “how do I look professional” moment - I was having a style crisis at a more personal level as well. Somewhere between growing out of my clothes, growing into my body, being stuck at home during the pandemic with no reason to dress well, and transferring into a degree where constantly wearing a black hoodie was the norm, the only upgrades to my closet had been to acquire a few slightly more structured pieces I could wear to formal events and interviews. Of course, these had all been purchased in a haphazard manner, and so they were all in bland neutral colours. It’s true that neutrals tend to match everything, and your first attempt at an “adulting costume” should probably be forgettable and timeless. But I looked into my closet and hated it. I hated the kind of dresser I’d become.

One thing I’ve really struggled with while trying to figure out how I’m going to dress is balancing the somewhat clashing set of preferences I have. My personal style is a bit more on the formal side. I love clothing that is well tailored, with strong lines, nice details, and lots of structure. I’m very into outerwear, I love a good blazer, and I think you can never own too many denim jackets. But I also like to wear colours, and I like contrast. I love pinks, blues, yellows, oranges, and I’d rather wear pure black or white than navy or tan under most circumstances. When combined, these preferences tend to be a bit… much, especially when dressing on the formal side. I’ve been wanting to own a pink pantsuit for ages, and I finally do, but that sort of outfit strikes me as fundamentally unwearable in most offices. It’s way too visible and attention grabbing, especially considering that most people no longer wear suits on a regular basis.

Another consideration in my life is that I’m still a university student, and oftentimes I need my outfits to do double duty for both a school and a work environment. (And I also volunteer at my church, so often I need outfits to do double duty for school and church, especially if I have evening classes that day.) Different contexts tend to have different boundaries for what is “socially acceptable dress” in that environment, which of course, also depends on who the people you’re going to interact with. You might be able to wear a tuxedo at church, but not at work; you can wear a pantsuit at work, but not at school; you can wear shorts and a tank top at school, and maybe also at church, but likely not at work; you can probably wear a minidress with fishnets at school, but definitely not at work.

The distinctions don’t just stop at lines between what’s okay and what is not okay to wear; not everything is uniformly suitable, and the “safe zones”, as well as the porousness of their boundaries, differ widely. There is often an acceptable, baseline level of formality, and straying too far from it in any direction will generally mark you as weird and different, even if your outfit is still technically within the bounds of social acceptability. As an intern, if I were to wear a pantsuit to work every day in an office where the average dude wears a polo and chinos, it would definitely be a little bit strange and I would stand out quite a bit. We all have different comfort levels with this. Sometimes, you want that. Mostly, I don’t.

Dressing for hybrid school/work days is this delicate dance of trying to signal the right level of formality while still being mostly casual, or, at the very least, not looking overly corporate while still blending in with office workers (think turtlenecks but not button-downs). Some contexts have wider boundaries that give more room to play with; some have narrower boundaries, and some have weirdly shaped boundaries. But the mental exercise of figuring out those boundaries can be exhausting, and trying to find viable intersections between them (that also work with your current wardrobe) can be challenging.

Of course, you can choose to totally disregard what’s socially acceptable, and just wear whatever you want, but remember, all choices have costs.

Fashion is a language, or rather, a set of interconnected languages, and I think there is value and potential power in understanding the language of “professional” clothing. Formality is read in the cut of your clothes; it is in the fabric your clothes are made of; it is in your accessories how you combine them; it is in the types of items that you choose; it is in the colours that you wear. I have become hyper aware of what the people around me wear, because it is through identifying similarities and differences in how specific groups of people dress that we understand the social conventions at play in our “dress codes”.

For example, one thing I have observed is that women are likely to signal the level of formality they intend to project either through their pants or through their shoes. Blouses can be awkward, so a lot of people (including me) tend to wear t-shirts instead. Most of the time, jeans and a t-shirt still won’t cut it, but dress pants and a well-fitted t-shirt will, and you’ll get bonus points for heels. The other way works too; a t-shirt and jeans is casual, but tuck the t-shirt in and add a blazer, and you’ve brought it up a notch. Formality tends to be expressed through both the fit and drape of your clothing and through “looking like you tried”, while sticking to “timeless” silhouettes. Wearing at least one traditionally “formal” item of clothing makes it look more like you tried. That being said, items that cannot easily be put on and taken off (such as pants) tend to suggest a higher level of formality than outerwear, in my opinion. If you’re wearing dress pants, you’ve committed to the dress pants, and the only way to reduce the level of formality is to add more clothes to dress down your outfit, whereas a blazer can easily be removed to appear more casual.

This is where the idea of “dressing up” vs “dressing down” an outfit comes from, in my opinion. There is the base outfit, which consists of the clothes that are difficult to remove. Those suggest the baseline vibe and level of formality you’ve decided to project that day. Then there are the accessories and additional layers of clothing, which serve to push the formality meter up or down, but perhaps only temporarily. The great thing about wearing a blazer with a t-shirt and jeans at work is that I can take the blazer off when I’m at school so I don’t look like an alien. Knowing your silhouettes, fabrics and materials, as well as their associated connotations, is really helpful at this dressing up or down stage. Here are some general guidelines, non-exhaustive guidelines:

So, for example, to dress up a jeans + t-shirt outfit a bit, wear dark wash jeans, wear a thicker t-shirt and tuck it in, and accessorize with a belt and pendant necklace. You could wear an oversized blazer, which adds a sort of casual elegance to the outfit, the kind you might want when going down for dinner with friends. And last, but not least, you could wear dressier shoes, like kitten heels.

I think it is also worth noting here that there is a difference between a piece that is meant to be oversized and a clothing item that doesn’t actually fit. This is especially true when it comes to clothing that is traditionally more structured. If you want an oversized blazer, buy an oversized blazer in your size, or, for the love of God, get the blazer altered to fit you in the shoulders at the very least so my eyes don’t bleed. A sized up blazer won’t fit you in the shoulders, in the arms, or at the armpits, and the darts will hit in all the wrong places. Tailored clothes should always fit correctly. End of story.

Take this advice how you will. I hope it’s somewhat helpful.

I guess the conclusion to all of this is that adulting is messy, fashion is messy, and even simple things like “what should I wear??” can cause internal crises. Especially as an intern, I feel like there’s a lot of pressure to try to match the corporate culture you’re embedded in, since you’re new, don’t have much leeway, and are trying to blend in enough that your colleagues could see you as a permanent addition to their team. The safe band for what I feel like is okay for an intern to wear is a bit narrower than for a permanent employee, I guess: you can be a step above the norm in terms of formality, or a step below as long as you don’t do it constantly, but I think depending on the company, living too far outside of those zones could prove to be problematic.

At the end of the day, all we can really do is observe what others wear, practice putting outfits together, and evaluate how we feel in them at work. Don’t bother asking your colleagues about the dress code. You won’t get a real answer.