Clothing dilemma

Just venting…
So between dressing up for last night and this weekend’s closet clean out it is now obvious I need to get my clothes in order as most are too big, a bad fit, or too worn out/faded.
I really need to go through everything and sort out what needs taken in (every single one of my long skirts that are worth keeping and 3 semi sheer tops I love)
I lived for years with a few decent items and way too many pieced together, ratty things to have lost half my body weight plus and still be wearing worn out, ratty clothes or to have the few good items I have hang off of me or be pinned together.
And Yes I DO understand that lots of people would love this problem but the fact is I have only a small handful of clothes that fit me and are not way too big or small or stretched out/faded/damaged. 
I have quite a bit of clothes but most of it doesn’t fit.
In my actual size other than a few bras and leggings I have:
1 long short sleeve plain black dress,
2 decently fitted shorter black dresses,
1 skirt (out of 9 that need taking in or gotten rid of)
2 blouses
maybe 3 t-shirts (which is fine since those I love oversized so bigger is OK)
And some undershirts 

Before I start buying clothes I can’t afford and that assumes I can find anything I like I need to see what of the rest of my stuff is worth taking in (especially skirts since long black skirts are hard to find)

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