I like what JB did with B/X headgear on his blog--the idea was that all characters should start with something distinctive to make them easier to remember and give a little kick-start to role playing as the player explains the character's headgear.

JB organized his chart by class (not ideal for Old School Hack: the Fictive Way, with 40 templates and counting.) After using the table and sort of bending and hammering it to make it work, I knew I'd do one for Old School Hack to focus in on how I want to use the chart. Even though it was not a perfect fit, the idea was so great and the results so entertaining the players clamored to get a fancy hat when they made their characters.

Anyway, it'll post next week, but it's on my resource page. I encourage you to take a look at Old School Hack Headgear and consider letting players earn their characters some Awesome Points during character generation by agreeing to abide by the random result of some rolls to whip up a magnificent hat!

http://fictivefantasies.files.wordpress.com/2012/03/old-school-hack-headgear.pdf