It would probably be beneficial to copy the idea motivated by the image linked below. The individual has selected and photographed meaningful combinations of his clothing. While I’m not particularly vain, it is clear that engaging with my wardrobe would help me to rid myself of what is numerically a nightmare of items. I have a bizarre assortment of pre-college/marriage/grad school/etc. clothing.
I’ve encountered many pieces of advice about wardrobe reduction over the years and the perspective was always negative. This series of photographs focuses on the positive aspect of intentionally selecting combinations of clothing. It seems to me that it would be easy to replace damaged or over-worn items with relative ease when necessary because it would be clear what part of your wardrobe had been lost. I also imagine that this would keep my closet from becoming too unruly because I would truly know what was in there.