My own feelings about gear have definitely evolved over the years. During classic WoW, the list-maker in me salivated over the relatively small selection of upgrades. I loved farming for a rare piece that granted some infinitesimally small (but infinitesimally satisfying) bump in my stats. But along about Wrath of the Lich King, I started losing track of what I was wearing. With so many choices and such comparatively high drop rates, upgrades began to seem all rather inevitable. My focus shifted from anxiously plotting my next move to a laid-back, almost nonchalant philosophy of covering the basics and then getting on with the game. Frankly, I'm quite certain I wouldn't be able to list every piece of gear I have currently equipped. Set it and forget it.
How much does acquiring gear factor into your current playstyle? Are you a progression raider eagerly chasing best in slots, squeezing out every last drop of power? Are you pushing hard to hit a particular ilevel to support a certain level of play? Must you have All The Hats? Are you a transmogaholic?