I am in the same boat as cindysmith. I've lost some weight, and almost all of my old clothing is now too big. Not oversized, but BIG. When I try them on, I feel like a child playing dress-up in mommy's closet.
As I got bigger in the body than I wanted to over the years, I also started wearing more "fluid" (but in my case, it was still mostly just a size bigger) fits, so most of the things I have/had are quite large. I am now more aware of what too big looks like, but I still struggle sometimes with the categories. I don't wear bodycon, generally speaking, so I've been trying to stick to tailored and fluid.
Angie's comments, as usual, were particularly enlightening. I do feel better when one key area - especially the shoulder line - fits properly. I have trouble distinguishing fluid or oversized from just plain too big when there is a dropped shoulder line, so I avoid those items. For the first time in a very long while, I'm not just going with a size bigger so an item doesn't cling in the wrong places, meaning I have to try on multiple sizes sometimes. This is a particularly timely topic for me, so thank you for starting the thread! I am learning a lot.