The Pillbox Hat Round and brimless, this hat's worn either centered or back on the head. Though the style was first launched in the 1930s, Jackie Kennedy revived the look. Generally this hat looks best with suits and fitted sheath designs, but it's super with most other silhouettes.
The Picture Hat. The most classic hat. Wide-brimmed and typically constructed out of straw, picture hats are sometimes swathed in netting and organza. Either way, they conjure up images of croquet parties at Jay Gatsby's and all those 1930s movies draped in garden party chic.
The Cocktail Hat. This broad category includes toques, pancakes and beanies, to name just a few. Small and brimless, they sit tilted or perched atop the head, usually accented with flowers or a spray of long feathers. A cover of net or nose veil typically wraps all or part of the face.
The Turban. Adapted from Eastern headdress, the classic turban is a piece of fabric that wraps around the head. Trendy in the late 30s, the 40s ushered in some interesting variations, mixing functionality with chic. Their fame began with women workers who kept their hair safely out of the machinery with scarves tied up turban-style.
The Cloche. This close fitting helmet-like hat worn low on the forehead, with or without a brim, was all the rage in the 1920s. Today's versions are mostly felt, and complement vintage dresses and suits. The Cloche looks best over a bob or other short, spunky hairstyles.
The Derby or Bowler-Rounded top, smaller brim, usually made of felt or straw, goes well with suits.