I have a couple of them and they are by far my favorite hats. There used to be a surplus store near where I grew up that we would frequent for camping gear, so I have a fair bit of surplus items. As for 'the look,' I think the trick is boxing up caring about the look and storing it someplace far away, and focusing on the fact that functionally it's a great piece of kit.
Along those lines, I wear overalls a lot and at first, my wife said don't you worry about looking stupid? I definitely don't wear overalls to look good for anyone, they're just nice to work in. With pants my drawers ratchet up and downstairs gets to be like a tangled hammock, not so with overalls.
Long story short, fast forward to the part where you say f-it, even if you're not bald yet!