I don't know where you are but having grown up in the Los Angeles area I can offer reasons for there.
When i was in school your weren't cool unless you were a surfer. You had to own a surfboard, have sun bleached hair and wear color blocked surfer trunks. They had the pockets to store your wax for the surfboard, car keys since surfing left you sitting on the board out in the water -- not by a towel on the beach --and some change to get a soda or call for a ride. The designs have varied through the years but the basic surfer trunk with the lace at the waist has pretty much held true. Some longer and baggier suits have come long but disappear to the standard of the surfer trunk. Boxer Shorts underwear was really popular in college. I remember "boxer rebellions" where all the guys would show up to parties wearing only their boxer shorts.
I think getting guys to give up hanging loose for tight undies or swimwear isn't and easy task.
However -- there were beaches that weren't surfer hangouts and other styles like speedos were still part of the mix. Venice Beach (also known as Muscle Beach) was always popular by body builders wearing the next to nothing posing suits and Santa Monica was pretty much a free for all of styles.
Between the surfer look and the Beach Boys songs, and the California look seemed to set the trend that for some reason has never changed.
I do remember the Duran Duran videos that featured the guys in black speedo briefs, they started to appear at pool parties more, but it wasn't enough to overcome the long tradition of those surfer trunks. Damn. No matter what we think or would like, the truth of the matter is that unless the teens decide that speedos are cool, there is little chance to see their popularity surge again soon.
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