Don't leave home without it
A few thoughts:
1. Putting on the gear doesn't make me reckless; for me it is a tangible reminder of the risks involved and starts the process of getting in the right mindset before getting on the bike.
2. I'm a serious partaker of the Aerostich kool-aid: Roadcrafter two-piece, Combat Tourer boots, Shoei full-face, Hurd Steve gloves. All of it, every time, or I don't get on the bike.
3. Given #2 above, my only challenge is that at 6' 7", my Roadcrafter takes up a lot of room -- there isn't a top box on the planet big enough to store it in (that will fit on my KLR) so I have to either wear it or find a place to store it at my destination. This is not usually a problem (I've taken it off and stashed it in the shopping cart), but I take the cage when I think it will be more trouble than it's worth.
In my dreams I'd like a bigger gear wardrobe -- maybe a Darien for the colder weather, the mesh Kevlar gear from Motosport (?) for the summer. But the Roadcrafter handles temperature and weather extremes pretty well, so I live with it.
For me, the bottom line is that I'd hate to have to explain to my wife and kids, from the hospital bed, why I got all banged up because I couldn't be bothered to take 2-3 minutes to put the gear on.