It's a sticking point with me, unfortunately. I had jumped-up-mall-cop types confiscate my pocketknife a couple times as a younger man, so now my collection has a special subset of cheap 'riskable' knives I carry in unfamiliar situations, to complement my nicer "edc" knives. Similarly, the sentimental knives mostly stay wrapped up at home, only getting broken out on occasions that fit them. When my uncle was in town, I carried the Buck 303 he gave me when I was a kid. On his birthday and the anniversary of his passing, I carried the 501 my dad gave me when I went off to college. A few others like that.
It's ridiculous, I know -- they were given to me to be used, and none of them are what you'd call 'safe queen' material. They're just tools, right? Well, yes.
...and no.
--Mark
(TL;DR: It's all in your head. But then, so is everything, isn't it?)