I have a quick test on whether it should go or not, and it goes like this:
Take item of clothing out of the closet.
What was the first thing that came into your head, Keep or Toss?
It’s that simple.
If you want something a little more objective because you ended up with a Half-Keep, Half-Toss feeling, then:
1. Check for rips, stains, tears, fading
Is it still in decent condition to be worn out?
If it is pilled to high heaven but you still love it, wear it (I do this to my cobalt blue stripe top), but if it is all pilled out, faded to a dark grey from a black and stretched out, then toss it.
2. Imagine it in the store right now & cash in your hand
Would you buy it again? If not, get rid of it.
If you wouldn’t buy that colour, fit, cut, and type again, then don’t keep it.
Now that you’ve decided, then put it in a box or a garbage bag and leave it there. Don’t open it for 6 months.
If you don’t miss it, then you can rip open the box to sell the items individually without any guilt or stress, or donate it as-is.