Everybody has those days. The ones where you try on the entire contents of your closet and nothing looks or feels right to you. Those days bite. It’s easy, on those days, to give into the temptation to just buy something new, but that’s not really the best way to deal, I’ve found.

I try, on days like that, to analyze what’s going on and figure out why I feel that way. Is it because I legitimately don’t like what I own? Am I trying new outfit combinations that aren’t working? Is there a tried-and-true look I can pull off? If that’s the case, it solves the immediate problem. If it doesn’t, it’s usually just a bad day and I vow to reassess when I’m feeling more myself.

If it’s more complicated, I start to reassess my closet. I’m at this stage now with skirts – I don’t want to wear the ones I have and I’m trying to decide if it’s because I need to replace them or if I’m just not feeling skirts. Here’s what I ask myself in this case:

  • How does this make me feel? Why?
  • Does it look good? If not, why not? Is the fit off? Are there unflattering details (ruffles, pleats, etc.)
  • Does this reflect or enhance my personal style?
  • How will people perceive me in this outfit? Does that fit with the way I want to be perceived?
  • Is it comfortable? Does it fit my lifestyle?
  • What can I pair it with to make it work for me?

These obviously aren’t the only things I think, but they’re the big ones.(And I’m not proud – a lot of these ways of thinking about clothes I picked up from What Not to Wear. The show does make people a little cookie-cutter, but it gives really good guidelines on how and why we like what we like and how to think about clothes in a more analytical way.)

With short-to-medium length skirts I currently own, I think the problem is fit. The weight I’ve lost in my hips is making them slip and slide all around me. I need to either have them taken in or give them away. But I am, I think, afraid that the weight loss isn’t permanent and I’m going to need them to be bigger again. It’s ridiculous and I need to let go of it, but I’m just not ready. A lot of these skirts I’ve had for ages and I really genuinely still like them and feel they fit my current style.

So that’s something I need to let go of and figure out. I’m thinking taking them in is the way to go. I need to figure out how to make the skirts work for me. Right now, I’m just letting them hang in my closet and take up space.