Many of us don’t wear hats.  We’re at a loss when confronted with the occasion that warrants wearing one. We didn’t learn the basics along the way.  We don’t know the difference between a pillbox and a boater because we didn’t grow up surrounded by people who wore hats.

That’s why I decided to create a simple guide to classic hat styles. I will admit to self-interest since understanding hats leads to wearing hats which leads to buying hats.  Hence the self-interest.  Okay, so disclaimer aside…I focused on 12 classic hat styles. Before I progress much further, the first thing to know is that that there are 2 key parts of a hat: the crown and the brim.  The crown is the top part which touches the head and the brim is the horizontal part that sticks out.  This description will probably have milliners everywhere up in arms but you get my point.  It’s also worth mentioning that not all hats have both parts; turbans, berets, pillbox hats, peach baskets, coolies, Juliet caps and fez hats only have a crown.  Tennis visors only have a brim.  So for every rule, there are quite a few variations.

Listed below are some classic hat styles that many of you will recognize but may not have the name on the tip of your tongue.  That’s okay. In no particular order, the hat styles consist of:

  • Boater: typically made from straw this hat was originally worn by French sailors.  The crown has straight sides and the brim is perfectly horizontal.  I think of this hat when watching regattas in the 1920s.
  • Cloche: fits close to the head and covers the ears.  The brim can be facing downward or rolled up.  This style hat was all the rage in the roaring 20s.
  • Cartwheel: a large brimmed hat that slopes downward.  Think of a wheel on a covered wagon but a tad more stylish.
  • Turban: made from fabric that is draped around the crown.  This hat reminds me of Hollywood starlets from the 1930s.
  • Beret: a soft round cap without a brim typically seen in France or Spain.  It fits snuggly on the head and can be shaped.
  • Pillbox: a small hat with straight sides and no brim.  Made famous by Jackie Kennedy in the 1960s.
  • Breton: a brim that is turned up all the way around.
  • Mushroom: The wide brim on this hat slopes down resembling the top of the vegetable it’s named after.
  • Peach Basket: the shape of this hat resembles a basket used to hold fruit picked at an orchard.
  • Coolie: A conical hat from Asia.  Frequently used when working in the rice fields.
  • Juliet Cap: a small cap worn with evening clothes
  • Fez: a cylindrical hat of Turkish origin sometimes featuring a tassel.

Remember this guide is simply a starting point.   There are tons of variations on each of these hat styles. I encourage you to keep it as a handy reference (you can print it.)  Let me know about other hat styles that you think I should include.  You can always use the contact page to reach me or just share this post along with your comments.