I have one of these in suede that I picked up somewhere. It wears really well. I wish I could find more.
I’m a big, though not hugely fat, person, and I have a big head, but it’s narrow across, so hats with brims seem to look silly on me.
Speaking of fedoras, there’s a little guy (maybe 5’7" or so, and slender) where I work who affects a fedora, and he just doesn’t carry it off. He always reminds me of Elisha Cook Jr trying to look tough, and failing.
Roddy
That’s sorta where I’m at now… but sunburned scalp sucks shit, and if I shaved my head my wife would probably murder and/or leave me, which would really suck.
oh, not even shaved once just to see? well, i’d say find a hat YOU like and wear it, the only opinions that matter are your’s and your wife’s. everyone else can step off, its your head, you’re the one wearing the hat.
What happens if you lose all your hair naturally? It’s your hair, not hers. If she’d leave you because you didn’t have hair, that doesn’t speak well to her grace or suitability as a partner.
No, I’m not telling you to leave her. I’m telling you to do what you want to your hair. If she leaves you over that, that’s disgusting and it’s not your fault.
A Panama hat can do well on older guys. And it’s true that nothing is as classy as a fedora.
Derby
Jamie from Mythbusters has a full face with a shaved head and he wears a beret. I don’t know if he actually looks good or if I’m just used to him. 
But it’s another option if you don’t want a brim but you don’t want a lot of hat either.
Apropos of nothing:
“I call that the best hat for a balding fat man!”
“Cover your head, you son of a bitch!”
I’ll just be going now.
Just saw a guy on the news. Fat and wearing a fedora.
Not a good look.
I’m leaning towards a slouch hat or boonie hat. While I appreciate the above suggestions, having ear and neck protection as well as something covering the top of my head is pretty important.
I’m not too interested in what other people think of my appearance, but I will make an attempt not to look like some hipster douchebag.
Pith helmet.
I’ve not left the house without mine in the last 10 days.
That is what I came in to suggest. Best hat I ever bought. Keeps off the sun and the rain, is comfortable and the LTM6 Airflow has a nice vent along the top that keeps my head cool.
A dunce cap. Fat, bald, and stupid is the best way to go through life.
Consult the expert: - YouTube
Thirding or fourthing the Tilley option…thisis the one that I own (I am also a fat bald guy as seen here) and it works great to keep the scalp burn-free.
Mark
I’m definitely in the required demographic. My son bought me this for Father’s Day and I love it.
Second the Tilly option! I have thisone and wear it all summer. I’m 65 and overweight, OK, maybe fat, but not too fat.