
When I was a kid, I wore those cheap give-away baseball hats you get at Giants games. Their cheap plastic adjustable bands ensured that no hat would ever actually fit anybody. I always yearned to have a "fitted" Giants cap. I had just such a hat that I wore across the Atlantic. It made it but lacked one important feature. Adjustability.
Sailing is not static. The waves push you up and down, the wind gusts and lulls, changing directions at a whim. The boat rocks back and forth. No one hat should be expected to handle all of these dynamic conditions.
Enter the velcro-adjustable wind-sensing cap. At the dock, you get to wear it at whatever setting looks good, but once you hit the open seas, vanity goes out the window (err, port). You set the hat just tight enough so that a gust won't blow it off. As the wind increases, you tighten the hat, keeping it always just tighter than the prevailing wind conditions. When it starts hurting your head, you reef. This is important so I'll repeat: when the cap starts hurting your head, you reef.
This is where the velcro adjustment comes in. The only proof I need against evolution is that sailors (and Moms) don't have a third hand. If you have one of those golf caps that requires taking the hat off, turning it inside out, adjusting some weird clasp, and then putting it back on to see if it's the desired tightness, you've already rounded up and should be thinking about picking up that lost crew member out of the water. It's all about the one handed velcro adjustment, takes no more than half a second to fit it just right.
A handy set of velcro adjustable settings, consider this the Beaufort scale of hat adjustment:
This isn't a science of course. Some sailors have rather large heads (see Dennis Conner), others are more appropriately sized (see attractive sailor pictured with this article). The important thing is that there is a hat for every wind and head combination.