We have BigBrother BigSister come by once a month on their regular rounds so all we have to do is put stuff out in the driveway and they take it away. So every single time I challenge myself to get rid of things. At first I could get rid of a lot of clothes but now that it's been months later it's more challenging to find clothes to donate. I've already gone through and re-through the clothes pile to get rid of extras.
So now for clothes it's at the point where I like all the tshirts I have left - but do I really NEED 15 tshirts? Many people in the world only have 1 or 2 items. They would be thrilled to have one of my tshirts. So by donating one or two items I can really help others out. I certainly would still have tshirts to wear in my closet.
All of my hanging clothes now fit in one closet, where before they were spread across two. So that is definitely progress. I still have a number of "work clothes" (suits, blouses) from when I used to work out of the house. I hold onto them in case I need to go out somewhere and be professional, but at this point if I haven't needed to in ... 8 years? ... I imagine I can give these away and wear one of my dresses if I really have to. That way someone else who does need to interview for a job can have them.