If your head circumference is 23.5 inches or larger, most headphones will feel too tight, leave red marks on your ears, and cause headaches within 30 minutes.
Clamping force is the primary issue. Headphones use spring tension to grip your head, and most are designed for average-sized heads. On a larger head, that same spring stretches further and clamps harder.
The Sony WH-1000XM5 extends further than most competitors, fitting head circumferences up to approximately 25 inches. The weight distribution is even, so the clamping force doesn't concentrate on any one point.
The Beyerdynamic DT 770 Pro uses a spring steel headband that naturally loosens over time. A common trick: gently stretch new headphones over a stack of books overnight to reduce the initial clamp force.
The Philips SHP9600 has massive earcups and deliberately low clamp force. It's one of the most spacious headphones available, designed for relaxed home listening. The trade-off: open-back design means no isolation and weak bass.
Over-ear always beats on-ear for big heads. On-ear headphones press directly against the ear, and on a big head, the clamp force makes this painful quickly.
