In the past I would use the what-if method and usually kept most items. Now, I use a different method that has proved itself to me several times. When working with clothing I choose an article I absolutely adore and an article I couldn't care less about, like a holey sock. I then pick up an item and try to feel what emotion comes up. Does it match the feeling when I think about or hold the adored item, or do I feel bleh like when I think about or hold the holey sock. When I started to use this method I didn't feel much at first. It takes practice to notice the subtle feelings when they arise. I never paid attention to them before, so it is a process. Another way to achieve a similar result (until I master the first method) is when I pick up an item and it takes me several seconds to decide, or I feel confused, or indecisive. If it takes me a while to decide, then I know I most likely don't want it but feel guilty or fear discarding it. The guilt may be because it was a gift and the fear may be because my anxiety leans me towards the what-if scenario.
What if I need it in the future and have to purchase it again. In these cases, I place it in a pending pile, a pile that I will leave until after I have gone through everything else. Because I made so many decisions going through my clothing usually by the end of the session I feel much more confident and am able to blow through the pending pile. On occasion, I keep the pending pile for a couple weeks to see if I find myself thinking about any of the items in it. Most of the time I don't and end up discarding it. Sometimes I keep an item or two and a couple months later end up discarding them. Think of each decision as practice. Practice to hone in on how each item makes you feel and practice making decisions. Making hundreds of decisions back-to-back will increase your self-confidence whether you think you need it or not. It's just a fact. When you practice something, you get better at it. When you practice making decisions, you learn to trust yourself more. I'd say it's a win-win situation.
Below is the mountain of clothing and the bin of shoes I went through.
Below is the aftermath of the discard. Simon has claimed the discard pile. It ended up being 7 yard waste sized trash bags of items that were donated. SEVEN YARD WASTE SIZED BAGS! That is insane! There is more clothing and shoes around the corner that wasn't in this photograph. The weird part is, 3 months prior I decluttered using the what-if method, this clearly proves the what-if method doesn't work well and I discarded that method as well.
We bagged up the rest (except for Simon), took it to a goodwill story and felt a huge weight lifted. We slept well that night.
Check out all these hangers that were left over!