Straight? Gently curved? Bent like a barrel? Multiple variations mark the way guys shape (or don’t) the brims of their baseball caps, and I’ve always been of the “gentle curve” persuasion.
Ten, maybe 15 years ago, there was a big movement to an exaggerated curve, almost as if the bill were wrapped around a beer can. Today, there’s a broad mix, including the blade-flat style that’s even more popular on the urban fashion scene than it is on the baseball diamond.
My friend Ed kindly pointed me to a great piece in The Plain Dealer of Cleveland in which Indians players explain their choices in shaping the bills of their caps.
As to how to orient the cap itself, readers of this blog probably won’t be surprised that I wear mine straight on, never cocked to the side. For guys of my generation, any cap bill that’s off center is straight out of the “Little Rascals.”
Buckwheat say, “No way!”
p.s.: My posts have been infrequent of late, as I’ve been distracted by a cross-country move, a new job and a few other associated details. I’ll crank up the frequency come July.
The Ball Caps Blog 
Slightly curved, and worn straight, are my preferred ways as well. Hope the move and the new job are going well.
Having worn a baseball cap every day for the last 25 years, I definitely have some preferences. For me, it depends on the cap style and manufacturer.
I love the ’47 Twins’ Cooperstown Collection of caps. With these, I love the very hard brim so pulling the brim “around a beer can” works well. I work in the yard in those. Go to hot, summer games in those. Sweat a lot in those. (modest sweat stains even make these hats look a little better!) The tight barrel-role brim with these looks… rugged.
The traditional, “game-day” New Era caps, especially the new ones, have unfortunately a very soft brim (especially if they ever get wet, which hats do). I’ve never been able to pull off the same barrel-shaped look with these as the both the brim is too soft and the crown sits up too high for my liking. So it’s much more “natural” to go with a gentle curve with these, as you see most players do.
And try as I might in the mirror (for the fun of it), I’ve just never been able to pull off the C.C. Sabathia or Pedro Strop straight-brim-cocked-to-the-side look.