If you are balding your hair will look better shorter. Just cut it shorter, then buzz it down grade by grade over a period of time to allow you and others the chance to get used to it.
Powerful Truth. I haven't gone sly, but I am doing the no-guard buzz and it's
so much better. My situation's recession (which isn't so horrific yet) and diffuse thinning (which
is), and while the thinning's not so apparent when there's length happening, if the wind hits it wrong or you sit under the wrong light, it looks like crap. Basically, I was thinking about it all the time, even if maybe mostly looked okay.
But buzzed, yeah, you're basically bald. But what hair there is looks so much better and you don't have to concern yourself with how it looks from angle because it looks the same from every angle. In my case, the thinning on top isn't particularly apparent this short whereas with even a week or so's extra growth there's an obvious horseshoe deal happening.
I'm not sure when or if I'll go full sly (more likely the more top goes), but even just the buzzcut is a tremendous load off. It's not even so much about any kind of confidence boost, though you may totally get one, it's about how you don't have to bother thinking about how your hair looks anymore, which in my case was so much that not having to think or worry about it was a surprising relief.