He who dies with the most toys wins!!
with the caveat that-so long as "he" does estate planning regarding the 'toys' distribution individually (vs. 'you can all fight over who gets what' aka-'evenly distribute my property among my heirs'), and periodically purges junk so it doesn't make it a p.i.t.a. for whomever has to deal with it in the end (this coming from dealing directly w/going through, cleaning up, trying to document/determine current value/store/arbitrate fights among heirs in order to distribute 'toys' from 7 decedents/estates in the thankless role of 'executor' or 'trustee').
I am waaaay less thoughtful and determined than you describe, in fact this would be me in the sun hat scenario: I didn't like the sun in my eyes on my last island vacation and today Hadley posts about a straw hat.
I've got another vacation coming up and maybe I should get a straw hat too!! I'll think (off and on) about what stores around here sell sun hats and maybe Google hats a time or two to get an idea of what I like. One day I'll have a few spare minutes while I'm out and be by a store and decide to stop in. If they have a hat I like I'll buy it (if I like the price). I might even buy a hat I don't like very much just to get the job done. Or I might leave the store empty-handed and decide finding a sun hat isn't worth the bother. I'll go on my next vacation without giving it another thought. - until the sun is in my eyes again and I wish I had a sun hat like Hadley's! 
. But he has no use for "stuff." He lives in a cheap studio apartment, all of his furniture came from Goodwill. I think his laptop, cell phone, and lamp are the only things he ever plugs in.
. I don't go to the clearance section because I don't want to buy things simply because they are marked down. I needed pajama pants this weekend. I went into Kohls, grabbed two pair and was out the door five minutes later. I didn't look at anything else because I didn't need anything else. For me that works. I know it isn't for everybody.