Tails has always been pretty flexible in many areas, especially his tails. To keep up his agility Tails does his usually leg lift routine, to make sure he doesn't get any cramps during flight. Would be bad if he suddenly stops in mid-air. So to help his body be more relax he puts his legs up and expose his retro gym outfit to you. You know the one with the bloomers that look like underwear. He also wears nice tube socks because he likes to razzle and dazzle during work-outs.