My favorite memory around boxers was when I was on the track & field team in middle school. Our uniforms had those tiny short shorts, but they had the attached briefs on the inside. So, you know, your junk was a little more secure and your underwear was hidden. Some of the guys didn't understand that these shorts did not mesh well with boxers, so when our uniforms got assigned, some of the guys walked out of the locker room with their boxers poking out of their shorts. Some had also tried shoving them inside of the briefs, so their shorts were all lumpy.
Quickly they learned boxer briefs and bicycle shorts were an excellent combination for wearing under their uniforms.