Low Crown is the way.
Here's the deal- if you have a massive head, check out the Studio Hat. These hats are low crown and fit like a canvas dad hat. The fit is a line drawn in the sand, it spits directly in the face of the absurd dorky hats that have overtaken trail running. Opt for something clean and low crown if you are willing to dance with modernity and not reach for relics of the 2010's.