Awhile back, Rob Scallon—one of the most popular and talented members of the world's growing online guitar community—posted a helpful video dedicated to helping players choose the string gauge that works for them.
You can check out the clip, titled "String Gauges 101," above. Bear in mind, this is clearly a "101"-style video, so Scallon covers a lot of very basic, but still helpful, information.
Since we're on the topic, let me recommend the little-known .095 string gauge. It's exactly what it sounds like—a gauge that's between .009 and .010. I've been using .010's for decades, but they never really worked on my vintage-spec (baseball-bat-necked) Tele-style custom job. Since going down to .009's would be ridiculous (they are, after all, rubber bands), I tried 9.5's, based on a friend's recommendation.
They're exactly what this particular guitar needed; it's now my go-to guitar, my most-playable ax, by far. They're a bit on the "9" side, but when weighed against all the competing factors, it all works perfectly.
I'm not sure why more companies don't make .095-gauge strings, but D'Addario makes a very nice set or two.
Anyway, that's all from me. Check out the video!