Well what I wear are called trunks i think. They are like boxers but tighter and have real nice support and a good nicely shaped pouch to hold it all together and in the right place. Or sometimes commando, usually only if I am away and run out though...
I usually wear boxer briefs when the temperature goes below 50 degrees Fahrenheit, but normally I just freeball it.
As an older man, I have seen multiple trends in underwear come and go. When I was a boy in the UK men and boys wore loose fitting boxer shorts. For my generation of teenagers in the 60's these were not at all stylish. They were what your dad wore, they featured in comedy films and theatre farces. For us the hip underpants were keyhole briefs like Y Fronts and similar brands. The Mod fashions of the early to mid 60's featured tight fitting jeans/trousers to which voluminous boxers were totally unsuitable. In addition, as youths we had to endure frequent and prodigious spontaneous erections often at the most inappropriate times which were deeply embarrassing because your penis was in no way restrained by loose fitting underwear so that a 'stiffy' was impossible to go unnoticed. I was desperate to change over to briefs at fifteen and very glad of the support and containment they provided keeping everything discretely in place. By the end of the 60's the fashion for hipster trousers meant high waist briefs with a keyhole opening had been replaced by smaller 'tanga' style underwear. then in the 80's an advert for Levis set in the 50's featured a smouldering Nick Kamen removing his jeans in a launderette. He was meant to wear Y Fronts the go-to underpants for young men at the time but objections to the close fitting briefs which highlighted your genitalia forced the ad agency to shoot the scene with him in boxers. Over night, Boxers became cool and briefs out of favour. Later, a hybrid of emerged the 'trunk' combining the shape and cover of the boxer short with the close fit and support of briefs. To date, briefs have returned to the repertoire of some major designer brands but have yet to regain a major portion of underwear sales. Apart from the inevitable association of boxers with my youth, personally I could not get on with them. I cannot believe that I (or any man) looks anything other than ridiculous in baggy undies and they fail to support and contain resulting in a lack of comfort throughout the day. (And no, I am not implying I am excessively endowed beneath mu underwear and no longer have to fear unexpected erections!) For several years I opted for the compromise and wore designer brand boxer trunks but a few years ago I shifted back to The type of underwear I have always trusted, designer brand briefs both with and without the keyhole opening finding them cool, comfortable and and supportive. More recently, I have discovered #'summmer weight briefs and trunks mad in China from an incredibly light stretch fabric which my wife has endorsed as 'cute' and attractive.