I'm a hat guy. Even before I went bald, lol. I wear a hat every day I leave the house and my collection keeps growing. My goto for summer adventure and boating is a
Shelta Seahawk with boonie style crown:
Yeah, it's pricey. But all their hats have a molded plastic insert in the brim that keeps them from flopping. Thirty knots running my boat up the marsh and it doesn't fold over. Plus it's light weight, it floats, it sheds rain, has a hidden pocket in the crown, and enough room in the crown to keep my head cool in the deep south. Seriously, I have boxes of cheap boonie hats but this thing is a game changer. If you're a boonie hat fan you owe it to yourself to check their line out.
In the winter I usually wear my rain hat for outdoor stuff, a
Bailey Dalton It's a cotton-poly blend fedora that sheds rain like a duck and has a wide enough brim to keep the drips out of your collar. Kind of between a Tilley style and an Akubra cattleman's hat:
Only down side is that it's stiff enough that the brim drags the headrest, have to take it off while driving. Mine has a custom oiled leather band these days and a couple feathers for good measure.
I also bought a WIIIIIIDE brim straw surf hat recently that works great in the sun but gives me a different look than the Shelta when I'm hanging out and not working too hard. And there's a whole collection I for the rest of my life - wool, straw, even a custom Panama hat made to my spec. Some guys like watches, I like hats.