Good luck! I need to do this as well. My wardrobe is a mess.

I'd love to know how it turns out!! Wishing you the best of luck

This is a good question! Previously when I felt this way my first thought would be to declutter something. As in, the first action I take when I'm bored is to declutter. Now when I'm bored, my first thought is to keep it. Let it hang around for a bit, because every year there's at least something (usually multiple) that I rediscover and am interested in wearing again. All I needed was a break from it. Last year in specific was a really wonderful year for that as I rediscovered several old pieces I was determined to give away at one point because I wasn't wearing them and they're favourites now! If, it's been multiple years and I'm still feeling that way I strive not to declutter something until I understand why. Boredom or disinterest are surface level reasons (for me personally). What specifically don't I like about this item? If it's not getting wear or doesn't match my style why? What about it? That grey cardigan I held up and waffled on was something I said I didn't like a few years ago because I wasn't wearing it but had no idea why. I could have just decluttered it, but now that I've kept it and tried to style it I've learned that the problem isn't so much the colour or the shape, it's the function. I don't like this item because I can only wear light weight items underneath. I don't own a lot of these items, and it's generally too cold for me to do this in the winter, which leads me to passing over it and not wearing it. I can use this knowledge to create frameworks for future purchases. That was a bit long-winded but I hope it helps!

@shawnaripari Thank you for answering so thoroughly. Having a break from something, to then find it interesting again later, makes sense. I move things around the house for a similar reason. It freshens the decor up without actually buying anything to do so. Working out why you dislike something so that you then don't make the same mistake again is a great idea. It had never occurred to me to use that reasoning. Thank you, I shall try to implement that into my own way of doing things.