1.) Have you worn this in a year?
2.) Are you keeping this for a specific purpose? (like say I would wear this if I ever went on a cruise to Alaska) and
3.) Are you keeping this because you feel guilty? (like your aunt knitted it and she is 80 years old with bad arthritis. Wear it once for her and get rid of it)
I applied these things to everything I owned. I ended up with two very large boxes full of clothes I did not wear, fit into, or really like.
A few of the items ended up with my Mom, but thats fine because she will wear it/it fits her. The boxes have since been getting fuller and fuller. Once I went through everything I made a list of everything in there for when we give it away. At the same time my Mom, randomly mind you, went through her own closet and got rid of about 20 items she never wears or doesn't fit into. I had to really push her to get rid of some things, but it was for the best! =) Since then we have regularly been adding to the boxes. Really anything that we suddenly think we don't want or care for anymore.
The cats got a joy out of the boxes the first night. They just can't help themselves.