Cardiff Girl, I recall reading a book called “SHED your stuff, change your life” or something like that. The main point: Editing leaves space, both literal and in your mind for your next creative venture. There is no need to have plans for anything in advance. Uncertainty in this case is good. Obviously, Covid has left all of us with an extra dose of uncertainty! I remember following the advice, editing my belongings and somehow over the next few months the plans for my unique (at the time) career evolved.
Like you, my youngest, 23, just left home, this time for good (I believe). He has paid off his student loans and saved money while working remotely. He recently found a better position and moved to Denver (three days ago). So empty nest…and I have started to edit, although I started with my makeup drawer.
A good portion of wardrobe editing has to be done alone, however, I find it helpful to involve someone I trust with the more difficult and emotionally fraught decisions. A trusted helper can steer you through the fuzzy logic we all experience around items with emotional ties that blur our vision. They do not have those ties. DD28 has become my trusted helper for editing. Sometimes I use a friend, although I find DD more helpful.
I have used many of the suggestions already made above, especially trying things on! So important!! A helpful question for some items may be: Am I able to create an outfit out of something else I already have for (imagined occasion) without this item? If so, which outfit would I prefer to wear? If it’s not the outfit with the questioned item, it goes into the edit bin.
Another helpful strategy is to look at similar items, if you have them, and eliminate the items you use least often, or not at all.
There is no magical way to recover the lost money from something with tags remaining unused in my closet. I have learned from experience that I rarely if ever decide to wear things with tags after the first season they were purchased (unless they are a suit). Keeping them does not reduce my guilt or somehow make the bad investment better. Sunk cost.
If I am too attached and think I may use something again, I put it in a holding zone and set a time limit. My holding zone has containers with future dates. When that date comes I will sort the bins and if I haven’t already pulled out the items, will make a decision to edit from my life or add back to my closet. I have a keepsake box for certain items however, it’s pared down to only a few of the most sentimental.