Sometimes you get so used to the fit of the baggy clothes that you don't realize that it's time for a new size.
Luckily I have my mother to tell it to me straight when I need to go down a size
In the summer when I was first starting to lose weight I got a lot of my mother's old clothes because she was about two sizes smaller than me. I really needed them because some of my shorts and capris were falling down. I also luckily had Torrid shorts that I bought on clearance back in January that had been too tight on me. I wore those all summer and by the end they were falling down!
I was also able to wear some of my middle school summer clothes, but that was the extent of my "skinny" clothes.
I've just been shopping sales and clearance and buying a thing or two here and there to get me by (like I LITERALLY had no work clothes because my other ones were 14/16s) because after a while I had passed my mom by in sizes.
I've given her a lot of my clothes because she recently went down a size

so it's been a big clothing swap.
I really think I'm going to stop soon so I can probably start buying clothes again!