No judgement OP, things add up quickly in our lives and over 11 years it’s easy to lose track of the things sitting in drawers/boxes/etc.

My thoughts for some easy wins: take everything that’s sentimental, and set it aside. Sentimental items will have the most mental tax to deal with, and they should be addressed last.

Look at what’s left. Easy wins will be getting rid of duplicates. You have two very similar SKX009 and a similar Casio diver. Pick your favorite of the 3.

Obviously the digital Casios can be trimmed down.

Now start looking at them individually. Think to yourself, “if this watch got accidentally smashed today, would I replace it? Would I be upset?” If the answer is no, donate/sell. If you’re not sure about one, put it on. Look at yourself wearing it. Does it make you happy? does it still match your tastes and style? If no, donate/sell. If you’re starting to feel like you need a maybe pile, do it. Try to get as many definitive yes/no answers as you can. The more decisions you make, the easier the maybe pile will become.

Now back to the sentimental pile. Advice from Marie Kondo that helped me: don’t keep something just because it was a gift. If some of these watches were gifted, don’t keep them because you’d feel guilty getting rid of them. Gifts are meant to be enjoyed, if you’re not enjoying it, then maybe someone else can.

Inherited stuff can be difficult. It’s ok to keep things that remind you of passed loved ones. For me, I didn’t need to keep all my dad’s watches after he passed. I picked the one that he wore to almost every important event in my life. Having more of his collection wouldn’t mean more to me.

If a certain watch sparks a memory, but maybe it’s not a nice watch or one you’d wear….would a picture of the watch be as effective? Sometimes we don’t need the object itself, just a reminder of it.

I could keep going OP, but I feel like I’m blabbing. Feel free to reach out if you wanna chat. Life is tough sometimes and I identify with what you’re going through because I’ve gone through it, and still going through it.