I carry pretty much all the time when I'm bush hogging, simply because of all the darned cats that show up. I can start cutting and within 20 minutes, I'll have four or five cats prowling around, just about all the time, it's easy to tell they ain't pets and nobody close to me has cats. (My garage cat stays up around the garage, he doesn't join in).
Holsters were a pain to wear on the tractor and my tool box is under the seat, so I went with a lightweight concealed carry vest. It has a pocket fairly high up under my left arm, easy to get to wit the velcro closures and I've never worried about losing it. It doesn't get dirty, but even so, wouldn't make much difference since I clean any pistol I take out before I return it to the safe.