So, yes, lots of good hats out there. My all-time favorite, despite its huge look-like-a-dork factor, is the Outdoor Research Seattle Sombrero ($56; www.orgear.com). Made with seam-taped Gore-Tex, it's the most rain-shedding lid on the planet. To really complete the dorkiness, be sure to use the chinstrap even when it's not windy. But seriously, I've had one for years and always have it stuffed in my pack or perched atop my head. REI makes a cheaper knock-off simply called the REI Sombrero ($30; www.rei.com), which uses a polyurethane waterproof-breathable fabric.
For whatever reason, Outdoor Research is the one company that has thought hard about hats. So in addition to the aforementioned Seattle Sombrero, another favorite hat in my arsenal is OR's famous Hat For All Seasons ($64 with liner), a bomber-style Gore-Tex hat with a removable fleece liner. The name here is no marketing gimmick, either. When I was on Denali a few years back it was my ubiquitous piece of headwear. I wore only the liner in the tent or under a helmet, and the shell (and sometimes the liner) when it was cold outside. It's fabulous! And, unlike its less sartorial sombrero cousin, the perfect complement to a soft-shell jacket.