26 years old, hairline is starting to recede/thin out. Looking for advice.

I've never really styled my hair, and I have a barber IQ of 0. Whenever I go to the barber I just say something like "take it down to an inch or so," I never requested any specific styles. From there I let it grow until it's hard to manage, and then I repeat the process.

Styling has always been difficult because my hair is extremely curly and uncooperative. Obligatory pictures of my hair over the years, oldest to most recent: http://imgur.com/a/egl0x

Any and all advice is welcome. Right now I'm considering just shaving my head, both of my brothers do -- seems like only a matter of time before I'd be joining the club. Something like Adam Nolly Getgood, Matt Halpern (usually wearing a hat or beanie), Devin Townsend, Jens Kidman, or Scott Devine. Maybe it would be better to just go shorter first? I am still very capable of growing a beard (here's a picture of six months' progress, probably enough to get stopped at airports).