3 Unexpected Things Working In A Super-Casual Office Taught Me About Myself

When I entered the professional workforce at the shiny young age of 22 and found myself in an extremely casual environment in my first job out of college, I thought I was living the dream. That’s what us millennials are supposed to want, right? No formal dress code and all the free office coffee you can drink?

At first, I did love the casualness of my office. I loved not having to dress up in skirts and heels or a mandated uniform. I could be comfy and casual, which was extremely important as I adjusted to the oppressive heat of summer in Florida. Eventually, I moved on to a new job and another casual office, this one even more laid-back than the last. Again, it felt awesome and liberating at first. I could wear yoga leggings, and no one would bat an eye. I could wear shorts and have it be completely normal. (Did I mention how hot Florida is?)

Somewhere along the line, though, I started to fall out of love with the casualness that I’d become accustomed to. To be quite frank: I’m kind of over it. I find myself longing for structure and a bit more formality. Not having a dress code has somehow made getting dressed in the morning more stressful. Though I’m grateful that I’m not in a position requiring me to shell out for pantsuits and pumps (my wallet is truly #blessed in this regard), keeping it casual at work isn’t necessarily all it’s cracked up to be. I’ve learned some important things about myself and how to navigate an uber-casual workplace without losing my GD mind. 

1. You will enjoy the casualness…for a while.

As I said, I initially wanted to jump for joy at the thought of having free rein to wear what I wanted to work. I am acutely aware how difficult it can be to cultivate a business professional wardrobe and an off-duty lineup. I’m truly grateful that’s not part of my current reality. However, as with a lot of hyped-up things, extreme casualness at the office gets old. 

2. You will be confused by some co-workers’ decisions. 

An important thing to realize when you enter a casual workplace is that everyone will take “casual” to mean something a bit different. Casual to you could mean nice jeans and a classic tee. Casual to your co-worker could mean leggings and a tank top. When there are no hard-and-fast rules, people tend to make them up on their own, and they will rarely (if ever) exactly match your own. 

3. You will feel conflicted.

I have struggled a lot with how I’m supposed to feel about my extremely casual office. Part of me feels obligated to enjoy this time in my life and really live it up – lean into the casual before you find yourself needing to wear blazers and pencil skirts every day! Another part of me, though, desperately wants to bring more formality to my work, through clothes and other ways. Because that’s the big thing people don’t think about when considering a casual workplace: Dressing casually can often lead to the work being taken casually — from the way people speak to each other, to completing projects, to meeting deadlines. 

Think about it this way: Clothes, like popular songs on the radio, can mark stages in our lives and take us back to a specific time. So if you were to dress how you did in college, wouldn’t it be easy to fall into acting like you did in college? There’s a reason certain professions wear the clothes they do. Would you be able to take lawmakers seriously if they were showing up to the House floor wearing sweats? What about if your financial advisor came in looking like she’s ready to go to the beach? Those are two extreme examples, but my point is, clothes say a lot about how you view your current situation and yourself within it. 

I can’t say I have all the answers when it comes to navigating a casual work environment (and some people might be reading this and wondering how I’ve turned this into a problem), but I’ve found a few guiding principles that help me:

1. Decide how you want to feel at work, and dress like that.

If you are most creative when you’re comfortable in a pair of stretchy leggings, then do you. If a tailored blazer makes you feel like a badass ready to kill that presentation, then rock it. As long as you are not violating a policy or have someone explicitly telling you an item is inappropriate (which is pretty rare in my experience with casual offices), I suppose there’s nothing stopping you. The point is to figure out what clothes are going to help you be the best at your job. 

2. Have your Oh-No-No’s list.

Remember Tom Haverford’s “Oh-No-No’s” on Parks and Rec — the list of characteristics that would automatically end a relationship if committed by one of his girlfriends? Get yourself a workwear Oh-No-No’s list. These are items that you decide are off limits for wearing to work. For me, the No. 1 item on my personal Oh-No-No’s list is workout leggings (not to be confused with dressy leggings). If I can wear them to the gym, I do not wear them to work. I kid you not: I tried putting on workout leggings to wear to work one morning, and I literally could not bring myself to wear them out of my apartment. I knew they were setting the wrong tone for my day and how I wanted to show up at work, so back to my closet I went.

To be clear, your Oh-No-No’s list is not binding. It is not a place for judgment. It is not a place to feel bad about yourself or your style. It is simply you setting a comfortable boundary about what works for you.

3. Just because it’s casual doesn’t mean your clothing choices don’t say something about you.

Unfortunately, no matter how casual your office is or what policies are or are not in place, you will still be judged for your clothing choices. It’s just the way the world works. Giving people the freedom to dress as they wish does not change that. I’m not saying you need to change your style or worry about what every single person in your office thinks of your style, but be mindful of what message your personal presentation sends. 

4. No matter the dress code, clean and neat is always a safe choice, as is being professional.

When in doubt, go back to basics. Show up to work looking fresh and polished, which can simply be making sure your shirt isn’t wrinkled and running a brush through your hair. It can also look like putting on a full face of makeup and wearing your version of a power outfit, if that’s your thing. Being presentable is a good baseline, and it doesn’t have to be difficult. 

Additionally, professionalism doesn’t have to be stuffy and crammed into a two-piece suit. Communicating respectfully, doing your best work, meeting your deadlines, and representing your company well can be done while wearing jeans and sneakers. 

I can’t tell you I have everything figured out, and I’m still going to feel conflicted about how casual my clothes and office are some days. Ultimately, I’m working toward finding a happy middle where I can enjoy the freedom of dressing in what makes me feel best and not worry so much about whether I should be more formal. The important thing is knowing what’s going to set me up for success and allow me to be confident in any situation work throws my way.

Claire Cole is a Midwestern native currently living in sunny South Florida. When she’s not creating marketing campaigns in her day job, she’s reading every book she can get her hands on and trying new baking recipes (to varying degrees of success). Feel free to say hi on Twitter (@claire_cole18) and Instagram (@claire_cole18).

Image via Unsplash

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