I keep receipts for every tool I bought since moving out of my parent's house. Owning and maintaining vehicles, homes, yard equipment, etc. requires quite a few tools. I always buy tools as needed for a job and justify the tool because of the money I save doing it myself.
I also am very involved with glass, wood, and metal working. I even have a few antique tools that I got just because they look cool. I don't like to think about what I've spent, but there are no regrets.
After quitting smoking 5 years ago, thinking about that wasted money does give me regrets. (14 years x 1-2 packs a day)