1920s Men’s Hats: Complete Your Great Gatsby Look!

Last Updated: October 24th, 2023 by Kerry Wisby (Teacher-BA English Literature, 1920s & Great Gatsby Expert)

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Hi friends!

This is Kerry, and if you’ve read any of my blog posts before, you know I have a passion not only for the 1920s but for hats of all kinds!

In the Roaring Twenties, men’s fashion underwent a transformation that left an indelible mark on the fashion landscape.

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At the heart of this style revolution were the iconic 1920s men’s hats, accessories that not only complemented but defined the entire look of the era’s well-dressed gentlemen.

The 1920s was a time of great social change, marked by the exuberance of the Jazz Age and the end of World War I. These shifts in society influenced fashion, and men’s hats became essential elements of every outfit ( see 1920s Men’s Outfits).

From the classic fedora, casual or sporty hats and straw Panama hats to the ever-stylish newsboy cap, these hats added a touch of sophistication and personality to men’s ensembles.

Join me as I delve into the world of 1920s men’s hats, exploring their various styles, materials, and the cultural significance they held during this fascinating period in history.

Whether you’re a history buff, a fashion enthusiast, or simply curious about the past, this journey into the world of 1920s men’s hats promises to be an enlightening and stylish adventure.

Types of Men’s Hats in the 1920s

Heavens, where do I begin?

It’s interesting to note that women had more fashion choices than men, but when it came to hats, I believe that men had a wider selection.

I’m going to do my best to cover all 1920s men’s hat styles, whether it’s a hat to wear on an evening out you’re looking for or one to complement your Great Gatsby or Peaky Blinders outfit.

The Gatsby Boater Hat

The 1920s men’s boater hat with its flat crown and stiff brim epitomized the spirit of the Jazz Age. Worn with panache at social gatherings and rowing events, it symbolized elegance and leisure.a man wearing a 1920s costume of white shirt, pinstriped pants with red-and-black suspenders and touching his straw Brim Boater Hat

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This iconic accessory was worn as a more casual type of hat and remains a timeless emblem of the carefree and stylish Roaring Twenties fashion.

The 1920s Newsboy Cap

Sometimes called a flat cap, or in the infamous Peaky Blinders series this was known as a “peaky”, the newsboy cap was the general all-around favorite for the average man or the average guy doing those manly, everyday chores.a young man showing how to wear wool newsboy caps with black-and-white checkered shirt

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Today, this hat is known as a newsboy cap, but it has also been called the baker boy hat. It exuded a charming and casual flair. Worn by working-class men, the Peaky Blinders characters, and fashion-forward gents alike, wool newsboy caps added a touch of urban sophistication to any outfit. This versatile cap remains a symbol of vintage style, bridging the past and present effortlessly.

Newsboy Hats for Men Women, Classic 8-Panel Flat Cap, Peaky Style Irish Hat, Gatsby Beret Cap Wool Blend Tweed

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The 1920s Gangster Hat

1920s men’s gangster hats, particularly the fedora, became synonymous with the era’s underworld and its charismatic, rule-breaking figures.

Untouchable Fedora Mens Dress Hats Black with red and yellow feather accent

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These stylish, wide-brimmed hats, sometimes called The Untouchable hat after the movie, added an air of mystery and sophistication to the likes of Al Capone and John Dillinger. Today, they remain an enduring symbol of the Prohibition-era swagger and intrigue.

You can find fedoras in every color of the rainbow to match your suit or jacket or for plain old-fashioned fun.

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The Gatsby Panama Hat

Panama hats are still seen so often that you wonder if they ever really went out of style! Panama hats remind me of fedoras with the back brim cut off!

GATSBY MENS PANAMA FEDORA HAT in gray wool tweed material with black sash accent

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While these were sometimes straw hats (but different from the straw boater hat), most were made from a tightly woven pattern that made them look like they were created from fabric.

1920s Mens Fashion - Mens Panama Fedora Hat in brown straw material and black sash accent

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The Jazz Age Pork Pie Hat

This is probably my all-time favorite. Even the name is fun!

Mens Pork Pie Hat in Brown with grosgrain ribbon and multi-color feather accent

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The 1920s men’s porkpie hat was the epitome of youthful rebellion and style. Its flat crown and narrow brim gave wearers a distinctive, edgy look that resonated with the era’s jazz culture and countercultural spirit.

You probably remember this as the hat that Michael Grey wore frequently in Peaky Blinders.

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The porkpie hat became a bold fashion statement, challenging convention and setting trends.

The Old-Fashioned Derby Hat

Older gentlemen in the 1920s relied on the timeless and instantly recognizable Derby hat.

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The 1920s men’s derby hat, also known as the bowler hat, represented timeless sophistication and a touch of formality. With its rounded crown and curved brim, it adorned the heads of both urban dandies and working-class gents.

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This iconic hat encapsulated the blend of tradition and modernity that defined the Roaring Twenties.

The Top Hat

The infamous top hat was worn for formal occasions or by men of status and wealth.

Mens Dress Tophat in Black with black grosgrain bow ribbon and red accent

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During the 1920s, men’s top hats simply exuded unparalleled elegance and grandeur. These tall, cylindrical hats were symbols of high society, often worn at formal occasions and upscale gatherings.

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With their polished black or gray silk exteriors, top hats epitomized the refinement and class of the era, making a bold statement wherever they appeared.

What Is the Gatsby Hat Called?

In F. Scott Fitzgerald’s iconic novel The Great Gatsby, the hat worn by the enigmatic character Jay Gatsby is never explicitly referred to by a specific name. However, the description of Gatsby’s hat in the book suggests that it is a “white flannel” or “white duck” hat.

This type of hat was similar to the newsboy cap of today and a popular fashion choice during the 1920s, the era in which the novel is set.

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These hats were often made of lightweight materials like linen or cotton and were favored for their casual yet stylish appearance. In Gatsby’s case, the hat serves as a symbol of wealth and his penchant for luxurious attire, which is in line with his extravagant lifestyle and mysterious persona.

Most flat caps from the 1920s were quite floppy and loose, not the sleek styles we see today, but that doesn’t mean you can’t wear one!

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While there isn’t a specific name given to Gatsby’s hat in the novel, it remains an integral part of his character’s image, representing his carefully curated image as a wealthy and enigmatic figure in the Jazz Age.

Gatsby’s hat, like many other elements in the story, contributes to the overall theme of appearances versus reality that is central to the novel’s narrative.

What Is a 1920s Gangster Hat Called Today?

The hat most closely associated with 1920s gangsters is the fedora.

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Even today, the term “fedora” remains a common descriptor for this classic men’s hat style. The fedora hat is characterized by its wide brim, pinched crown, and is often adorned with a grosgrain ribbon or band.

It became a symbol of sophistication and allure in the Prohibition era, popularized by notorious figures like Al Capone and Bugsy Siegel. You’ll even see this type of hat called The Godfather, after the movie which began in the 1920s.

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In contemporary fashion, the term “fedora” still denotes this iconic hat style and continues to be a versatile accessory. Fedoras are worn by individuals who appreciate the timeless appeal of these hats, which can be found in various types of materials, colors, and designs to suit modern tastes.

While some may use the term “gangster hat” colloquially to describe a fedora, it’s important to note that fedoras are not inherently associated with criminal activity. In fact, they have evolved beyond their Prohibition-era associations.

Mens fedora in white with black band and accent and toggle Closure

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Today, the fedora remains a symbol of style and sophistication, and it’s a favorite choice for those seeking to add a touch of classic charm to their attire, whether for formal occasions or everyday wear.

Which Was the Most Popular Hat for Men in the 1920s?

This is a toss-up between the fedora and the flat cap.

Working class men and poor men would favor the flat cap. Business men would wear fedoras to the office.

The fedora hat epitomized the fashion of the era with its distinctive style featuring a wide brim and a pinched crown. It became a symbol of sophistication and urbanity, and its versatility allowed it to be worn for various occasions.

Men from all walks of life embraced the fedora, from gangsters like Al Capone, who added a touch of intrigue to the hat’s allure, to everyday city dwellers and businessmen.

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The flat cap was extremely popular with the working class, the poor, and young boys.

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You’ll see all types of styles today, most of these flat caps being sleek and streamlined. Back in the day, however, newsboy caps were loose, floppy hats that had 8 wool triangular panels that come together at the top of the hat with a button to secure the 8 panels in place.

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Whichever you decide to wear, you can guarantee that you will get tons of compliments on your style!

A Final Thought Before You Leave

Men’s 1920s hats were more than just accessories; they were iconic symbols of a bygone era. The Roaring Twenties witnessed a hat revolution with a diverse array of styles.

The classic fedora hat, associated with gangsters and urban elegance, reigned supreme.Mens Hat Black fedora with accent

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The boater and newsboy caps exuded a casual charm, while the bowler exuded formality.

Men's 1920s Brim Boater Hat Gatsby Straw Hat 20s Costume Accessories, straw hat with red and Black ribbonGet this Vintage Straw Hat! 

Top hats represented high society, and Panama hats brought a touch of tropical flair.

Gangster hat wool Stain-Resistant 1920s fedora hat

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These hats reflected the spirit of the Jazz Age, embodying sophistication, rebellion, and individuality. Today, these hats remain timeless, bridging the gap between past and present, offering a glimpse into a captivating chapter of men’s fashion history.

1920s Men's Hats: Complete Your Great Gatsby Look!
1920s Men's Hats: Complete Your Great Gatsby Look!
Step back in time with our guide to 1920s mens hats! Explore the iconic styles that defined an era of dapper fashion and sophistication.
Gatsby Flapper Girl