I had to cull mine too, and I hate throwing clothes away as I sew and often use material from clothes as practice pieces or for other patchwork things.
The only thing that worked for me was the reverse hanger tip. You have all your hangers with hooks facing forwards, then as you wear things you put them back after wearing/washing with the hooks facing backwards. After 3 months you then pull out the backwards ones (stuff you have worn) and if possible move them to a separate section or space in your wardrobe. This is stuff you will definitely keep.
You then go through all the stuff you haven't worn and decide on a set number of items to either donate, throw away, or recycle. But you only choose items that would have been appropriate for that season (spring, summer, autumn and winter) - you don't, for example throw away winter jumpers in June because you very well might regret that.
Also you start with stuff that is ripped, stained, stretched or just looking tatty, too big or too small.
In my case I chose 10 items - although there were probably more like 50 or 60 items I hadn't worn at that point.
After the first round of doing this I still had a lot of stuff I needed to cull, so I did it again after the next 3 months. Then repeated it for the rest of the year (4 batches in total). I really did get rid of a lot of stuff that way and didn't regret anything I got rid of. I do it now as a habit every 3 months and actually kind of look forward to it.
Hopefully it might work for someone else.