The Many Hats of the Great Gatsby

by Miranda Hilderbrand

It isn’t too often a film comes out that sparks great interest and conversation on hats and hat culture, but when it happens it’s always exciting and never on a small scale. It goes without saying that The Great Gatsby is THE hat film of the year and, once you see it, you’ll know why. Taking inspiration from the iconic style of the 1920s, the hats are a most welcome throwback to the era of glamour, sophistication and lots of razzle dazzle.

     With so many wonderful hats featured in The Great Gatsby, it is difficult to decide where to begin. The 1920s brought about new styles, designs and fashions along with new trends in hats. Some of our personal favorites from the era (and the film) are boaters, homburgs, fascinators & headbands, newsboy caps, and the cloche. And, while not a focus of Gatsby, you cannot envision 1920s hat attire without seeing the pork pie. Each of these styles has their own unique history and look that will transcend from the Roaring ‘20s to today’s world.

     A personal favorite from the film has to be the boater, or you may have heard it referred to as a skimmer, katie or cady hat, or even a can-can. With its historic roots going back the the gondoliers of Venice, to being part of the uniform for Ivy League schools, to a great hat for a picnic in the park, this was a hat for all social classes.  You would see it worn by the working class, the middle class and even the social elite. It is no surprise that you would see Tom Buchanan and Jay Gatsby sporting the iconic boater.

     Another hat icon from the era is the homburg – a hat that was often associated with royalty and world leaders. First created in the 1880s and made popular by King Edward VIII, it became the hat for formal wear for all gentlemen from the 1910s to the 1950s. Its size and shape somewhat resemble the softer, more casual styles like the fedora, yet it’s stiffness, curled brim and lack of the front bashes has given the homburg more of an aire of formality. It was very much the gentleman’s hat you would expect to see in elite high society circles of the 1920s.

     A more casual hat from this era is the newsboy cap. You may also have heard it called a baker boy, big apple, apple cap, eight panel, and even a gatsby (due to it’s association with the character from the book/movie). This hat is also associated with, you guessed it, the newsboy of the early 20th century which gave it the reputation of a “working class” style. However newsboy caps were commonly worn by all social classes. The hat also became very popular with well-to-do sportsmen and many golfers.

When talking about the hat fashions of the 1920s, one absolutely cannot overlook the styles worn by women. The true icon of the era for most women was undoubtedly the cloche. Straight from Paris, the cloche, meaning “bell” in French, could be seen in many fashions on nearly every woman’s head. You would even see them embellished with beading and lace for cocktail parties, soirees, and even bridal apparel. One of our favorite stories of the cloche has to be how women would use adornments on them to relay messages to onlookers. For example, a firm knot signified that a woman was married; a loose delicate bow signified a woman was in a relationship and unavailable; and a large flamboyant bow signified a woman was single and ready to mingle.

     The other styles that would be commonly seen on women in the 1920s are headbands and fascinators. The headband styles from this period could sit around your hairline, on your forehead or, in some styles, over your eyes. The piece that stole the show in The Great Gatsby was without a doubt Daisy’s diamond headband. Made by Tiffany & Co., the piece is set in platinum and adorned with diamonds and pearls and is sold for $200,000! Fascinators were also worn by ladies looking for a smaller headpiece rather than a full hat. Typically a fascinator is any hat that will not fit directly over the crown of the head and they are more often than not more playful and whimsical than a traditional hat.


     While it wasn’t a main focus in The Great Gatsby, we feel the pork pie deserves an honorable mention, as it was incredibly popular during the 1920s.. It is primarily recognized as the hat of many Jazz and Blues musicians in New Orleans. It’s name has a very literal meaning taken from the process in which they were created: food vendors would take battered old dress hats, trim off the damaged outer brim and re-block the hats over pie trays.

     With so many amazing styles to choose from, you can easily find your own piece of history that reflects not only Gatsby but the full vibe of the 1920s. If you haven’t seen the film yet, The Great Gatsby is an absolute must see. It is an amazing story and the hats alone are worth it! At Hatbox, we offer many of these styles from hat makers all over the world. Come see us and we can help you embrace your own inner Gatsby!