As a boy, it was tighty-whities all the time. At about age 11, I discovered that sleeping naked felt MUCH better but still had my daily TWs. Moved to England - school uniforms and TWs (as I recall, they were called "Y-Fronts" by the Brits) were required. Then, back in the States, it was a jock strap in gym, otherwise almost always free balling. I found it much easier to "position" the hourly hard-ons through my pockets if I didn't have to fight the TWs, too.
Even now, decades later, I still free ball much of the time at home (if I'm not already completely naked AND if it's warm enough).