In direct answer to your question.
In looking for a sun hat that I can roll with while on, I look for three things.
Tight or adjustable hat band.
Chin strap with a tight cinch. Or just put a knot in it.
Brim that is just stiff enough to stay fixed in the up (better visibility) or down (better sun and rain protection) position, but will easily give way to water pressure.
I like my OR Nimbus Sombrero. Cinch adjustable band. tight cinch on the chin strap. Soft flexible wire sewn into the edge of the brim. Otherwise very flexible brim.
First time I rolled with it, it came off onto my back with the chin strap around my neck. No sea sock style choking though during the roll. I felt it come off, but never actually felt it around my neck, probably in part due to the DS neck gasket.
Cinched up the hat band and chin strap a little more and no problem.
Only down side on the hat is that there’s a thin layer of foam in the brim to make it float. That foam retains a little bit of water for a little added weight and a little bit of latent dripping. Not a big deal to me, but I’d change that if I could.
I used to take my sun/rain hat off when rolling, but now for the occasional roll to stretch out, cool off, or just for fun, it’s more relaxing to just leave it on.
As someone else mentioned, if it’s enough shade coverage, a boonie works great.
I do agree with others, if you know you’re going into combat, or doing extended focused practice, then just a neo hood and/or helmet is the way to go. You can get put a flexible visor on the helmet or get a small visor on the neo hood if wearing the hood alone.
Paul S.
The dry hat roll
Before everyone got so damm good, I used to do the dry hat roll.
You would take your hat off (baseball cap for me) and slowly roll over and place the hat on the upside down hull still dry. Then you come around under from the other side, grab the hat with one hand and roll up using the paddle with one hand and place the dry hat on your head.
It’s harder to explain than do. Anyone who practices all those Greenland rolls can do it easily.
something like this?
http://www.kayakquixotica.com/alex-hd.html
http://www.dubside.net/swf/video_trickroll_brick.html
I've seen it done with a beer can. Apparently Brits have been known to use a top hat...
i use a visor
i got a big fat head…and visors fit me better…so i tighten it a bit if i am going to roll…
there has been a couple of times where my roll has taken longer because i saw the visor drifting away-and had to grab it…
r