I've given away all the emotionally important things that I didn't need day to day --childhood toys, etc. I know some of the recipients have guessed what I'm up to, but my cover story was good --downsizing with the intent to move into a smaller house-- and so far they haven't caused problems.
The rest of my nice belongings I have labled with colored dots --green and blue for family, red and yellow for friends-- with a letter code (M = mom, etc.), and have made up a key, so that when I'm gone things can be distributed easily. I have also written up a narrative of how to deal with the bulk items --these friends have their pick of my tools, these other friends have their pick of my library.
A formal will will take care of the legally relevant items --bank account, vehicles, property, etc.
I have emptied my dresser and closet and boxed up all my clothes, in such categories as can be easily managed: T-shirts and underwear can be thrown out, shirts and sweaters go to Goodwill, etc.
I have worked as a professional logistical coordinator, so I like making sure all the ducks are in a row. But at a certain point, ending my life is about letting go, acknowledging that I won't be here any more and that I won't have a say in how things are managed. There'll be an emotional mess when I'm gone, and whether my T-shirts get turned into shop rags or tossed into a dumpster will be a pretty minor concern, all things considered.