I've noticed a trend in what I wear regarding headwear.
Left-most Phillies hat: this is for grungy jobs outside
Middle Fightin' Phils hat: default I'm going out with kids, might be a little dirty hat
Right-most IronPigs hat: an occasion that will likely be clean and neat . . . summer formal attire
As for the Ted Williams and Gettysburg caps, they're for the gray area between what's described above.