If you like to wear vintage hats like I do, you'll want to consider how the hat looks with your hairdo. As hat styles changed over the years, so did coiffures. In the 40s, when victory rolls were popular, tiny "doll" hats were worn tipped to the front or the side to accent the hairstyle. In general, hats work best with short hair or up dos. The photos below are all from 1951 and show how hair can be styled to complement a particular hat.
Jacques Fath for Joseph Halpert.