I've got two: a fitted 1959 cap that I got as a Christmas present a couple of years ago, and a fitted 2005 World Series cap I bought at the ballpark gift shop the day of the WS parade in 2005.
The WS cap is my true go-to cap, though it's beginning to fade. Anybody know a no-risk way to clean it? It's a wool on-field cap and has shrunk slightly.
My son bought the '59 cap for me a half-size too big, anticipating shrinkage as happened with the 2005 cap. But the '59 cap isn't wool and hasn't shrunk, so we sewed some fabric in the headband to improve the fit. It becomes my go-to cap if the Sox have a string of losses when I wear the other cap.