My clothes wardrobe drives me nuts too!
I have clothes from a size 12 to a size 24. Because I work in business and live in a climate with seasons this includes business wear, work out clothes, summer clothes, winter clothes, casual wear, evening wear, etc..
I don't want to get rid of my "skinny" clothes because that is the size that I want to be again. When I lose weight I don't want to get rid of my larger clothes "just in case". I know that some people think it is good to get rid of all your larger clothes, but I've gained weight back too many times to not keep some or most of them. While I like shopping for clothes when I've lost weight, I despise having to do so when I've gained weight. (For every 10 pairs of pants or jeans I try on when I'm heavier I'm lucky if
one fits.)
It really doesn't help that we don't have a lot of storage in this apartment because I don't even have a lot of places to store clothes away. I've got clothes 18 to 24 in my closet and 12-16 boxed away. I need to clean out my closet, but I don't want to spend the time especially since I'm losing again and I'm hoping some of the smaller clothes fit soon. When I am losing weight I hate it when I forget which clothes fit me at which size. I'm often pleasantly surprised when I find clothes I've got tucked away. Because women's clothing sizes have changed in America over the years and they were never consistent in the first place, I can't trust the size label to determine if it is something I can get into.
If I keep the weight off for a while I might just box away the larger clothes and put them in an actual storage space. That way it won't be convenient to slip into larger clothes if the weight starts creeping on, but I will have them if I god forbid I need them.