As some of you may have seen, I recently culled a bunch of dresses that no longer looked great on me, due to shrinking in the laundry or other problems. It felt good, but I’m still committed to dresses, especially as summer wear.

I used to feel that way about skirts. A midi skirt or pencil skirt was my go-to look, especially if it had a cutesy print. But I have a short waist, which means the midi skirts usually sit too high, and look awkward both ways if the tops are both tucked or untucked. I used to just go with it, but it doesn’t feel right anymore.

Pencil skirts used to be a problem, but I’ve clme back around on them. I used to have a great collection of brightly printed ones that were the first things I sized out of when I gained weight. I now have one skirt in that vein that still fits. I also have a couple of black ones (including black on black polka dots and the BR black lace, see finds.) I was scared away from buying pencils for a long time due to how quickly I had to give up my crop of them (I got a couple of seasons out of them), but I’ve gotten over it and may look for more over time. They are easier to pair with tops especially because things like peplums, that don’t need tucking, work. And my weight has stabilized so I’m no longer gaining, though I hope to lose some.

As for midis, I tried on a few midis in my closet this morning. I am wearing one, even, but it doesn’t feel like me anymore. I don’t know if the fact that I find them awkward to wear has colored this opinion. I have a beautiful one from Boden that has a birdcage print (see find), and I think I have to put it into holding because it comes up to two inches below my bra—but may fit if I lose weight by next year. Maybe I should just let it go now, but it’s a purchase from two years ago, and Boden is not cheap. Plus I do love it, and maybe it would feel more me if it fit better. Or maybe I’m just more a pencil skirt gal now.

I realized that flowy midis work better now, and I do have some skirts along those lines. I still like them, too. The one I have on today (see find J Crew) is less flowy, but has an elastic waist and fits better than the Boden one. My top untucked but I have a cropped cardi on to mitigate that problem a little. The untucked tee is too long on me, like most tees before I realized it was a problem feels bunched up and frumpy. I changed to tucked. It’s somewhat better. Problem is likely the T-shirt in this case, and I should really keep trying to find cropped styles, although I find that difficult for some reason. I do have two. I should have change to one of those shirts, but I ran out of time.

I also have one midi with a ship print from Anthro (see find) that I stalked for ages on eBay. I'd like to keep this if I can figure out how to wear it.

I did buy one skirt from Loft this year (see find), which is more casual with a fluid fit and knee length. I can tuck a top into it well. I also have a couple of casual and maxi skirts that are fine for weekends.

Anyway, I’m not sure what the point of all this navel gazing is, except to share how fashion evolved for each of us at different times. I won’t solve this issue overnight, but over time probably. I’ve nearly abandoned skirts, but I still want that option in my fashion toolkit, so I’ll be thinking about it. Looking for sizes and styles that can sit lower on my body is the number one priority. Obviously, I’ll be much pickier in the future, as I have been about every other type of item. I should do an outfit lab for every skirt in my closet, but that sounds exhausting right now.