When I was an undergrad, I don’t think anyone told me anything about dressing for work. That probably had something to do with being a philosophy major, and that major not having a specific “job” associated with it (maybe professor?). Then I went to get a Masters Degree, and I got a lot of confusing messages from everyone. You have to wear X every day, never wear Y to work, Z is only appropriate for A occasion. It still makes my head spin. However, in the 8 years since then, I would like to think that I have gotten a decent sense of how to dress myself (feel free to scoff at this idea the next time we see each other). Here are the two best pieces of advice on dressing I have ever received, and a bit about how I put them to practice.
1. Dress for the day you are going to have
Take a moment to think about what your day entails. Do you know whom you are meeting with, where and how you are going to show up? How would you want to dress in any of those particular situations? None of my jobs have a dress code per se, so for me it really comes down to my opinion on how I see my day going. I know I want to be comfortable, and I know I want to look good. For comfort, I just ask myself “am I going to regret wearing this in a few hours?” The same can be said for showing up to class. If I’m going to sit somewhere for three hours or more, I certainly don’t want to wear something that is going to make me hate it by the 90 minute mark and/or distract me from what is going on in the room. As far as looking good, well that leads to the second point.
2. Wear clothes that make you feel good.
Now I know that I wrote looking good in the last paragraph, and titled this section feeling good, but that is because these two things are, in my mind, inextricable. To me, the things that make us look good are the things that make us feel good about the way we look. So every morning when I look myself over in the mirror before leaving for work or school, I ask myself “do I feel good about how I look?” You would be amazed at how often the days that I say “absolutely” are the days that others tell me I look good, and those are also the days when I feel better about much of what I do. There is a sense of confidence that comes with feeling good about myself, and that translates into a lot more about my day.
I’m not going to make specific recommendations about things I think everyone should wear, because everyone who reads this has a different life. While I am a big fan of, for example, mixing floral prints with plaids (which can work very well despite what my mother tells me) I know that may not be what you all are going for. Also, feeling good about how you look doesn’t, in my opinion, have boundaries or norms based on our gender or other identities (despite what spoken and unspoken messages we get bombarded with every day). This gets at the core of my point, which is that if you feel good about yourself in what you are wearing, you are bringing that part of yourself into your work, into your interactions with others, and into the world around you. A friend that I’ve been emailing lately has at the bottom of their email signature “When you show up authentic, you create space for others to do the same”, and while I know they aren’t just talking about clothing, it still helps me center my thoughts as I get ready every day. If I can show up feeling good about me, maybe makes a space where other people can too.
 
Read more of Conor’s thoughts on his blog Life Work Balances>>