I think it comes down to two details - the rise, and the leg opening down by the ankle. Once you start getting into pants that hang very low, with a long rise, but sit low on the hips (as johnnynorman said), and have tapered ankles but billowing material in the legs, then you are into zoot suit, NBA player style. However, pants with a long rise, which are meant to sit high on the waist, with a non tapered ankle are very 1930s classic style. They were called "bags", and were very popular back then. The bottom leg opening was often as wide as 22 inches, which is much wider than today's trousers. Not for everyone, but I think they have a certain appeal.