I used to play this sad little game with myself whenever I was having a bad day- I would go into my closet and I would pick out my most hated outfit and wear with an angry kind of pride, as if I wanted to project to all of the world that I was having a bad day. I was determined to make myself look as ugly on the outside as I felt on the inside.

The worst was whenever I received a compliment at the office or out on the street about the outfit that I had chosen. I couldn’t understand how clothing that I felt made me look frumpy and bloated could be admired by a stranger. Maybe they were just being nice in order to mock me, or worse, pity me. Then I’d get angry and think, “How dare you try to ruin my bad mood with your kind words!”

I am so twisted.

One day I was explaining this weird little habit to a friend of mine when he held up his hand to stop me. “Wait, hold on. Why do you keep clothes that you don’t like?”

So maybe he was a guy and he didn’t really understand. Or maybe I was the one not getting it. After all, I had half a closet’s worth of clothes that I didn’t wear half of the time because I had grown sick of them, or because they were old and had fallen out of fashion.

I think I said something crazy like I needed variety and we both thought it was weird so he dropped the subject, but ultimately in this scenario I really was the crazy person because I could not let go of things that made me feel badly about myself.

It took a lot of soul-searching but I eventually decided that I did not want to be that person that held on to things for the sake of having “things”. I wanted, I deserved, to fill my home with only the things that I loved. Why shouldn’t that ultimatum apply to clothing and accessories as well?

So I purged my closet of all of the things that no longer fit, were bad choices, or- let’s face it- were just plain unflattering. My wardrobe was decidedly slimmer, but I was satisfied- it was actually really easy to give up an abundance of choices in favor of a smaller wardrobe full of favorites that made me look and feel good.

It may seem silly to think of re-organizing or purging your closet as something that can improve your life emotionally, but paring down my wardrobe using my new rule has given me a boost in my self-esteem. I still have the occasional bad hair day (like, pretty much every other day) but I’m buoyed by the knowledge that even though I might feel like I’m dying on the inside, outwardly I can project an image of competence and self-confidence and show people the best of myself even when I’m feeling at my worst.

Plus, it makes getting out of the door in the morning way easier for this night owl. Trust me on this one.

Have you undertaken a closet re-organization lately? I want to hear all of the grisly details. Indulge me below or drop me a line at keepingbusyb@gmail.com. And if you’re looking for even more inspiration on how to get your wardrobe just the way you want it, I’ve got some best practices for organizing your clothing and more here.