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When is Casual Too Casual?

Updated: May 24, 2022

When I started my career years ago as a hospital Administrative Assistant, I was surrounded by coworkers and leaders who came to work every day as if prepared for an interview, and quickly understood that appearance was important. Unfortunately, at that time, I could not afford to shop for work clothes and often felt embarrassed going to work because I knew that my appearance did not match what I brought to the organization.


I was lucky enough to have a leader who expected a high level of professionalism from me but also recognized my inability to "look the part”. She pulled me aside one day and had a very direct conversation with me about my attire. She suggested that I start looking at thrift stores because there was a great chance that I could find good clothing for next to nothing. She also gave me tips on how to make the most of my wardrobe until I could afford to do more. The goal was to always look my best even if I only spent $3 on the entire outfit (true story)! Her advice set the tone for what I believe has contributed in some ways to my career growth and I continue to use and offer this advice to others.



Throughout my career, I have worked for organizations that have loosened dress code requirements, I imagine, to create more inclusive environments that make employees more comfortable. Although, I understand the concept behind these relaxed rules, I have found myself at times looking at my colleagues and wondering if they meant to make a quick stop at the grocery store or come to work. I have seen flip flops, cut off shorts, see-through shirts, messy hair, over sized t-shirts, and my absolute favorite, bedroom slippers, the fuzzy pink kind! I must ask; at what point do we throw in the towel and call it inappropriate? Is there even an "inappropriate" category anymore? When as a leader is it OK to step in and say something is not appropriate for work?


To be clear, I am not saying that your appearance is the only thing that counts, nor am I claiming to be an authority on workplace attire, as I have been known to sometimes wear jeans to work (with a blazer). With that said, I also know there is something eternally powerful about looking and feeling your best every day! There is something about the ritual of preparing for work! You stand up straighter, you feel prepared for anything, and you command a certain level of respect without saying a word.


There have been times when I had employees ask me what I expected and I try to use these situations to challenge their own perceptions. I normally make a point to outline what the organization's expectations are, which is the most important, and then simply asked them to ask themselves the following questions before heading to work:

  • If a sudden opportunity arose for you to meet an important client, are you ready?

  • If a high-level leader of the organization asked to meet with you, do feel good about what you're wearing?

  • If you want to grow in your career, do you look the part today and every day?

  • Are you proud of what you see in the mirror?

  • Are you representing your best self?

If the answer to any of these questions is "No", then get back in that closet and try again!

I know that the corporate world is evolving and with this evolution comes new expectations of employees and leaders alike but there is something that I don't believe will ever change and that is our ability to choose how we present ourselves to others. In my opinion, taking the time every day to look your best says that you care and will care for your organization in the same way.

So, if I get a vote in any of this, I say save the flip flops and cut off shorts for a cool vacation and come to work prepared to show everyone you are the best choice for your position and any other opportunity that may be on the horizon!

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