So. The other day I had the idea of the Monks of the Cool. (Terry Pratchett, anyone?) The problem is, I've never homebrewed anything, and when I tried, it didn't turn out very well. If anyone else finds this idea worthy of a shot, please feel free to take it out of my hands. I'm going to list some of my ideas below.

Basically, the idea is a charisma based monk, with the possible idea of making a monk that actually doesn't suck. (I've taken some model out of the nymph monster)

Upon entering the monastery of the Cool high in the mountains, the applicant is taken to a room full of extravagant clothes. A single question is asked: "Yo, which of these clothes would look good on you?" The applicant is given an hour to consider.

The right answer is, of course: "Whatever I choose to wear."

It would probably be any non-lawful and any non-evil.

Possible class features:

Some sort of a Stunning Looks feature: after a certain level, when someone sees you for the first time, (s)he is stunned for 1d4 rounds with the DC of either 10 + the charisma modifier or simply the charisma score. After you've been once stunned you can't be stunned again for 24 hours. Suppressable at will.

Coolness Embodied: Add your charisma modifier to your AC and possibly to your saving throws. (Maybe later to your Attack Bonus for a round or two?)

A bonus to your Diplomacy/Intimadate/Bluff against humanoids and further bonus towards your own race.

Maybe - at later levels - an ability similar to the one you get from VoP where a manufactured weapon may shatter when it hits.