Fedora 

In the 1900’s, it was very common for men to wear hats out.  So common, in fact, that only the poorest men would be seen in public without a hat.  It was customary to remove one’s hat, though, when at home, or talking to women.  This may be why the pinched crown of the fedora became popular- the hat was easy to grab and remove.   

Fedoras have been worn by women as well as men from the very start.  However, movie greats like Humphrey Bogart portrayed detectives and gangsters with fedoras, thus giving the hat an edgy image.  This image has stuck to this day.  If you are looking for a little bit of no-nonsense grit in your wardrobe, a fedora might be for you. 

Cloche 

The cloche hat is close fit and shaped like a bell; it has a short brim which is typically upturned.  The hat was popular in the 20’s and early 30’s; so much so that it was a such a major part of the art-deco style. Women changed their hair style to closely cropped just to be able to wear cloche hats well.  After World War One, there was a (well earned) reckless abandon displayed by young women. The “Flappers” as they were called would drink, smoke, listen to jazz, and generally do as they please!  The cloche hat was the icon of this movement.  If you are looking for something that can be flirtatious and fun, a cloche might be right for you. 

Mad Hatter 

The hatter was a character in Alice’s Adventures in Wonderland by Lewis Carroll.  This character was never called the “mad hatter,” but it was assumed by his behavior, and the fact that the expression “mad as a hatter” had a very real origin.  In the 1800’s, a mercury containing chemical would be used in processing the fur pelts to be made into hats.  Milliners would often get sick from mercury poisoning. 

In the book’s illustrations, the hatter wore a wellington top hat.  This type of top hat with narrow brim, upturned at the sides, and the crown flaring out at the top, takes the formal top hat and gives it some pizzaz! Especially after Lewis Carroll’s hatter was through with it! 

Porkpie 

The porkpie hat, now, is made primarily of felt.  It has a narrow, flat crown and an equally narrow, flat brim.  What gives the porkpie its name is its rough resemblance to a pork pie: there is a crease that goes around the circumference of the top of the crown.  This crease allows the crown to telescope out slightly when worn. 

The porkpie hat was made popular in the 40’s when it was fancied up with feathers and colour coordinated with the zoot-suit.  It was worn by the renowned architect Frank Lloyd Wright, and jazz saxophonist Lester Young.  If you are looking for a slightly eccentric and truly artistic look, consider wearing a porkpie. 

Top Hat

The top hat was, and still is in traditional places, part of a formal dress code.  It was worn by the leaders in society (social, political, and economic) in the late 1700’s and 1800’s.  By the 1900’s though, there was a growing place for the semi-formal white collar worker.  These workers tended to prefer the homburg, bowler, or even boater.  By the 1960’s the top hat was largely rendered antiquated.  (The last president to wear a top hat at his inauguration ceremony was John F. Kennedy in 1961.)  Let’s face it.  If you are looking for a top hat, you are probably getting a costume together for a Halloween party.  But nothing exudes an image of luxury and prestige like a tuxedo with a top hat! 

Bowler 

This hat, iconized by Charlie Chaplin, was originally created in London by Thomas and William Bowler in 1849.  Originally, it was created to be closer fitting than the top hat, and thus more practical to wear for workers.  By the early 20th century, the hat became the favorite of businesspeople working in the finance industry.  It was considered a semi-formal hat. 

Of course, the bowler hat, or derby in the U.S., was the favorite of several comedians beside Charlie Chaplin.  In the U.S., Laurel and Hardy, and Curly Howard (Three Stooges) all wore bowlers.  If you are looking for a practical everyday hat with, perhaps, a bit of whimsy, the bowler may be for you! 

Fascinator 

The fascinator is commonly known as a small decorative piece that clips in the hair for special occasions.  Formally, though, a fascinator must have a substantial base (more than 10 cm in diameter) and is attached to the hair with a clip, comb or an elastic around the back of the head. Fascinators are decorated with feathers, silk flowers, or beads and the base is generally made of straw or sinamay. 

Fascinators have been worn since the Renaissance as flashy and perhaps more comfortable alternatives to traditional Christian head coverings required in church.  Now, you will need a fascinator when attending royal events.  Fascinators are also traditionally worn to up scale horse racing events like the Grand National, Kentucky Derby, and the Melbourne Cup.

Homburg 

The homburg hat has its origins in Germany in the late 1800’s and had a similar role to both the bowler and boater.  This hat was worn as a semi-formal alternative to the top hat.  The homburg hat is similar in appearance to the bowler, but it has a single dent running down the center of the crown.  Unlike the three dents of the fedora, the homburg was considered a slightly more “reputable” hat.  If you are looking for something different than the ever popular fedora, but more notable than a bowler, the homburg might be a nice alternative! 

Boater 

The straw boater hat was traditional to the gondoliers in Venice, Italy, but it became the favourite of the same crowd who would wear a homburg or bowler in the winter.  It was so popular that Americans had “Straw Hat Day,” usually in May, when people would switch from wearing the felt homburgs and bowlers to the lighter straw boater hats for summer.  This was a celebration of the changing season to summer and wearing a felt hat would be the equivalent of wearing white after labour day.   Now, a straw boater is a great everyday and practical hat for a summer day.