If you swim or take part in any other active sport you are likely to be using communal locker rooms, while you are changing the other guys will see your underwear and you will see theirs. The underwear that you wear says something about you, even if it is that your mother buys your underwear and you don't care about it.
In the days before shorts with built in liners guys tended to wear underpants beneath their shorts, the shorter the shorts then the briefer the underpants. Once you reach the point of wearing tiny running shorts with a bikini brief underneath then you are probably happy to swim in speedos.
Since the fashion for wearing low cut jeans showing off the top of the boxer briefs began, the underwear manufacturers have been printing designs on the boxer briefs to make them more interesting. Someone who wears "interesting" underwear is going to want similar standards for their swimwear.
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