In the 1930s, women's hair was fairly short and generally styled in finger-waves or soft curls with hardly any body. Long hair became the fashion in the 40s, even though working women were encouraged to keep it short. Popular styles included the pageboy, the Victory Roll, and barrel rolls. The 1950s saw the return of short hair, this time neck-length and with lots of wavy body. Longer hair remained popular among the younger crowd, with the ribbon-tied ponytail a mainstay.
Many people wear tap pants or bike shorts under their skirts.
For a little more style, bloomers can easily be made from a funky fabric and a boxer short pattern. The worst mistake you can make here is not wearing anything or wearing just underwear.