1920’s Mens Hats – Great Gatsby Hat Style

 

1920s style mens hats vintagedancer com

1920s Mens hats- The Cap, Homburg, Felt hat, and Fedora

Men’s hats during the 1920s ranged from season to season. Warm summers such as in the time of the Great Gatsby brought out straw Boaters, Panamas and Longhorns as well as linen flat caps. The cooler seasons kept men in conservative suits with Bowlers, Derbies and Fedoras being the best hat choices.

Unlike today men and women always wore hats. Every day, every occasion, called for a hat to match your outfit. Light colors in summer. Dark colors in winter.

Let’s take a look at the different styles of 1920s summer hats first.

1920s Flat Cap

1920s mens hat

1920s Check Cap

The hat that the Great Gatsby wears most is the flat cap. Also knows as Ivy cap, cab driver hats, newsboy cap, driving cap and big apple cap. It is made of 8 triangle panels that meet at the top with a covered button made in the same material. It has a small brim that the top rests on. Overall the 1920s cap looks baggy not the tight narrow Ivy caps you see today. In the summer these caps were made of a light colored linen or cotton poplin material and lined in silk for breath-ability. Inc cooler weather the caps came in tweed, herringbone wool, and corduroy as well. Darker colors were worn in the winter-blues, greys, and browns-in solid, plaid, and check patterns.

1920s hats Boardwalk Empire

Newsboy Cap- Worn in Boardwalk Empire

All classes of men wore these hats even boys selling newspapers on street corners hence the newsboy hat name. It was mostly a working mans hat from working class origins as a fisherman’s hat. It became a well to do men’s hat when worn with sporting clothes or upper class leisure clothing. For drivers it was ideal since there was no stiff crown to bump into the car roof. It remained a sport hat for golf well beyond the 1920s.

White Great Gatsby hat

1920’s Men’s Cap

1920s Straw Boater or Skimmer Hat

1920's straw boater hat

1920’s boater skimmer straw hat

1920s straw hat men

Douglas Fairbanks holding his Straw Boater Hat

Straw hats were even more popular for hot summer days than flat caps. Outdoor sporting became the new hobby for men and women. From tennis to biking to riding in your new car- the people of the 1920s were outdoor enthusiasts. Boating became popular and with it the Boater or Skimmer straw hat was worn. Hand-woven thick straw made for a heavy solid cylindrical hat with either a 2 inch or 3 inch brim. Skimmers had the smaller brims while boaters had the larger. Other than that their shape was the same. They each had a solid or striped petersham ribbon around the base. College kids and alumni often wore their college’s colors on their hat bands. Many men’s “gentleman’s clubs” also produced bands with their club’s colors.

Barbershop quartets are often associated with these hats. Popular in the 1920s for summer time entertainment they became the staple uniform hat for singing musicians.

1920s Panama Hat

1920's Panama hat

1920’s Panama Optimo hat

Another common straw hat for summer was the Panama, in particular the Optimo Panama hat. It was hand-woven of very light weight South American reed straw where it was woven and imported from Ecuador. It could be rolled up and tucked into a lapel pocket which made it very easy to travel with. The rolled crease down the center of the hat defines the Optimo style.

1920s mens panama hat

Telescope Crown Panama Hat

Both men and women enjoyed this style of hat. The other Panama option was the round telescope crown panama that more closely resembled a light weight Boater or Skimmer. Authentic Panama hats were quite expensive so only the elite could afford one.

1920s mens panama hat

Man Wearing a Panama Hat

Other styles of straw hats existed in the 1920s. While the shape doesn’t have a name they generally resembled their felt hat cousins such as the fedora.  From “Straw Hat Day’ in May or June or “Felt Hat Day” on September 15th only straw hats were to be worn, regardless of weather. It was a tradition that caused annual riots of hat smashing.

TIP: Don’t go budget on this panama hat. The non packable varieties need careful care to make sure the straw does not get bent. Once damaged it’s not reversible. Trust me, I’ve learned the hard way.

1920s mens hat panama

1927 Man Holding a Panama Hat

 

 

 

1920s Bowler or Derby Hat

1920s bowler derby hat

1920’s Bowler Hat

A few decades before the 20th century a man developed an oval shaped hard material hat for riding. The edges were curled all around and finished with matching pertersham ribbon.  It was designed to protect a man’s head while riding through bushes and ducking under branches. It remained a popular hat with men even without horses. Although materials softened a bit from the 1900’s hard hats the Bowler, also know as a Derby, was the most common men’s hat of the early 1920s. It was an appropriate alternative to the formal silk top hat. Black was the most popular choice although stylish men also had brown, tan or grey bowlers to match their suits. Towards the end of the 1920s when men’s and women’s fashion became bolder with color bowler hats appeared in blues, greens, and other more festive choices.

1920s mens hats the bowler or derby

1924 Man in Bowler Hat

In the summer months a bowler could be made of straw although these were less common. Usually they were made of light weight, light colored felted wool.

1920s mens homburg hat

1922 Homburg Hat

A cousin of the bowler is the Homburg. Worn in the decade preceding the 20’s the Homburg looked like a bowler with a long crease down the middle. They were also considered somewhat of a formal gentlemen’s hat. Black, brown and grey were again the primary colors.  Ribbon bands were quite wide, as they generally were on Fedoras and others soft felt hats too. The crown was tall and straight on the sides.

The Homburg quickly went out of fashion in favor of the soft creased Fedora by the mid 1920s.

1920s Fedora Hat

1920s ganster fedora hatIn the 1920s the fedora hat was just entering the fashionable scene for men. Previously it was a women’s style hat starting in the 1880’s. 1920s men’s fedoras feature wide 3 inch brims that were shaped downward on both the front and back side thus making the sides rolled slightly upwards. This shape was popular with young men who called it the snap brim or swagger hat style. Otherwise brims were turn up on one side and down on the other, a style preferred by more traditional men.

Fedora’s  also had a sharp crease down the middle that could be a single crease or a triangle shape with the base of the triangle at the back of that hat. Hats came uncreased when purchased so that the owner could decide how to shape it. Popular colors were olive green, black, brown and gray. Hats colors often matched suits but it wasn’t  a universal rule. While the felt fedora started out as a middle class hat, wealthy men associated with prohibition and crime, aka Al Capone and his gangsters, were icons for the hats in the 1920s. A solid color band, with flat bow wrapped the base of the hat. Usually the band was made of petersham or silk and matched the color of the hat. For extra style the band would be in a contrasting color like white on black. A feather on the side of the hat did appear on some hats but wasn’t very popular till the 1940’s.

1927 mens hats suits stripes peak

1920s mens fedora

Knapp Fedroa Hat Ad

The Trilby is another name for essentially the same hat as a fedora. Trilby’s featured tall crowns with a crease down the center, rolled up side brims and a wide petersham band with flat bow on one side. Common colors were black or brown with matching band. In the 1920s hats were almost always made of beaver fur felt.

Other fur felt hats came in variety of tall crowns with and without creases, indents, and wide brims. Some were crushable and some hard to protect heads while in labor jobs. They lacked specific names.

 

 

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1922 mens hats vintagedancer com

 

1920s Top Hat

1920s men Top Hats

Grey Top Hats

The mid height beaver fur or silk Top hat with curled brim was still the best hat for formal wear in the 1920’s. It had been popular for a century and remained the hat for formal wear for another 50 years or more.  It was an everyday hat until the 1920’s encouraged informality and soft hats in all matters of dress. Many traditional upper class gentlemen still wore them in business settings and especially democratic political gatherings. The younger generation thought they were a “vicious, vile, and ugly symbol of the ungodly Victorian” said Westminster Abby’s Canon Donaldson in 1927.

For most men dawning a silk hat was something only done at weddings and grand opera performances where men in cheaper seats found it more useful to have a collapsible silk top hat that they could tuck under their seats.

1920s mens hats vintagedancer com

1920 Types of Men’s Hats- Tops Hats, Bowlers, Homburgs, straw Boaters

Wearing 1920s Hats Today:

If you are lucky enough to find a 1920s hat in good condition then you are in for a real treat. Most felt and straw hats were well worn by the end of a season if not completely destroyed by the elements and frequent handling. Otherwise there are quite a few choices in new men’s hats that still embody the 1920s style.

Here are some excellent new 1920s Gatsby era style hats:

 

Bollman Collection Gngster 1920's Replica  Black Fedora with White Band
 

Bollman Collection Gngster 1920's Replica Black Fedora with White Band

$100.00

Buy at: Hats.com

Stetson Newsboy Cap- 1920s Tweed
 

Stetson Newsboy Cap- 1920s Tweed

$120.00

Buy at: Hartford York, Fine Hats & Accessories

1890s Bollman Collection Bowler- Ideal for the 1920s- S- XL
 

1890s Bollman Collection Bowler- Ideal for the 1920s- S- XL

$100.00

Buy at: Hats.com

Scala Mens White Straw with Ribbon Trim Boater Hat
 

Scala Mens White Straw with Ribbon Trim Boater Hat

$51.99

Buy at: WesternWear.com by Sheplers

Scala Panama Skimmer
 

Scala Panama Skimmer

$150.00

Buy at: Hartford York, Fine Hats & Accessories

Men's Borsalino Wool Newsboy Cap - The Garibaldi
 

Men's Borsalino Wool Newsboy Cap - The Garibaldi

$99.50

Buy at: Hartford York, Fine Hats & Accessories

White Gatsby Hat- JB Stetson Cap - The Hatteras Linen Newsboy
 

White Gatsby Hat- JB Stetson Cap - The Hatteras Linen Newsboy

$125.00

Buy at: Hartford York, Fine Hats & Accessories

Borsalino Ivy Cap in Houndstooth Print
 

Borsalino Ivy Cap in Houndstooth Print

$107.25

Buy at: Hartford York, Fine Hats & Accessories

Stetson Fur Felt Dress Hat - The Homburg- 1920 Men hats
 

Stetson Fur Felt Dress Hat - The Homburg- 1920 Men hats

$235.00

Buy at: Hartford York, Fine Hats & Accessories

 The 1920's Optimo Panama Straw Hat
 

The 1920's Optimo Panama Straw Hat

$350.00

Buy at: Hartford York, Fine Hats & Accessories

Wigens Cashmere Cap - The Exclusive Newsboy
 

Wigens Cashmere Cap - The Exclusive Newsboy

$123.75

Buy at: Hartford York, Fine Hats & Accessories

CTM Unisex Straw 2 Inch Brim Boater Hat
 

CTM Unisex Straw 2 Inch Brim Boater Hat

$26.99

Buy at: Buy.com (dba Rakuten.com Shopping)

1920s mens Brown Derby Hat
 

1920s mens Brown Derby Hat

$90.00

Buy at: Hats.com

Biltmore Panama Pork Pie - The Montego
 

Biltmore Panama Pork Pie - The Montego

$135.00

Buy at: Hartford York, Fine Hats & Accessories

Godfather Black Homburg 1920s Hat- Boardwalk Empire Nucky Thompson's Hat
 

Godfather Black Homburg 1920s Hat- Boardwalk Empire Nucky Thompson's Hat

$90.00

Buy at: Hats.com

Bollman Collection Replica 1900's Homburg Hat- Ideal for the 1920s too
 

Bollman Collection Replica 1900's Homburg Hat- Ideal for the 1920s too

$100.00

Buy at: Hats.com

Fairbanks Mens Twenties Fedora
 

Fairbanks Mens Twenties Fedora

$78.00

Buy at: Hats.com

Como Fur Felt Fedora Hat in Authentic 1920s Style
 

Como Fur Felt Fedora Hat in Authentic 1920s Style

$430.00

Buy at: Hats.com

1920s  Ganster Bateman Fedora
 

1920s Ganster Bateman Fedora

$161.00

Buy at: Hats.com

Galvin Tweed Cap
 

Galvin Tweed Cap

$75.00

Buy at: Hats.com

Wigens Ivy Cap - The Harris Tweed Hans Ivy
 

Wigens Ivy Cap - The Harris Tweed Hans Ivy

$90.00

Buy at: Hartford York, Fine Hats & Accessories

Genuine Panama Straw Fedora
 

Genuine Panama Straw Fedora

$95.00

Buy at: Paul Fredrick MenStyle

1920s  Mens Chaplin Panama Bowler Hat
 

1920s Mens Chaplin Panama Bowler Hat

$137.50

Buy at: Hats.com

JB Stetson Yachting Cap - The Allenport
 

JB Stetson Yachting Cap - The Allenport

$75.00

Buy at: Hartford York, Fine Hats & Accessories

Working Mans Hat - Wool Fiddler Cap
 

Working Mans Hat - Wool Fiddler Cap

$29.00

Buy at: Hats.com

1920's Mens Hunter's Plaid Cap
 

1920's Mens Hunter's Plaid Cap

$32.00

Buy at: Hats.com

Men's 1920s winter hat - Sheepskin Wool Hat - The Captain
 

Men's 1920s winter hat - Sheepskin Wool Hat - The Captain

$150.00

Buy at: Hartford York, Fine Hats & Accessories

JB Stetson Wool Newsboy Cap
 

JB Stetson Wool Newsboy Cap

$95.00

Buy at: Hartford York, Fine Hats & Accessories

Roll Up II Panama Fedora
 

Roll Up II Panama Fedora

$200.00

Buy at: Hats.com

JB Stetson Newsboy - The Plaid Wool Blend Hatteras
 

JB Stetson Newsboy - The Plaid Wool Blend Hatteras

$95.00

Buy at: Hartford York, Fine Hats & Accessories

Bailey of Hollywood - Derby Bowler Mens 1920s Hat
 

Bailey of Hollywood - Derby Bowler Mens 1920s Hat

$64.95

Buy at: Shoebuy.com

Bailey of Hollywood - London Derby Black mens Derby Hat
 

Bailey of Hollywood - London Derby Black mens Derby Hat

$84.95

Buy at: Shoebuy.com

Scala - Black mens Derby Bowler Hat
 

Scala - Black mens Derby Bowler Hat

$42.95

Buy at: Shoebuy.com

Henschel - 6413 - Olive
 

Henschel - 6413 - Olive

$33.95

Buy at: Shoebuy.com

Bailey of Hollywood - Tino 7001 (Men's) - Bluestone
 

Bailey of Hollywood - Tino 7001 (Men's) - Bluestone

$70.95

Buy at: Shoebuy.com

Stacy Adams - SAW545 (Men's) - Black/Grey
 

Stacy Adams - SAW545 (Men's) - Black/Grey

$45.95

Buy at: Shoebuy.com

Stacy Adams - SAW545 (Men's) - Chocolate
 

Stacy Adams - SAW545 (Men's) - Chocolate

$45.95

Buy at: Shoebuy.com

Stacy Adams - SAW545 (Men's) - Camel
 

Stacy Adams - SAW545 (Men's) - Camel

$45.95

Buy at: Shoebuy.com

Bailey of Hollywood - Thurman 22701 (Men's) - Natural
 

Bailey of Hollywood - Thurman 22701 (Men's) - Natural

$137.95

Buy at: Shoebuy.com

Bailey of Hollywood - Roll Up 22700 (Men's) - Natural
 

Bailey of Hollywood - Roll Up 22700 (Men's) - Natural

$119.95

Buy at: Shoebuy.com

Bailey of Hollywood - Roll Up 22700 (Men's) - Taupe
 

Bailey of Hollywood - Roll Up 22700 (Men's) - Taupe

$119.95

Buy at: Shoebuy.com

Stacy Adams - SAW536 (Men's) - Grey
 

Stacy Adams - SAW536 (Men's) - Grey

$44.95

Buy at: Shoebuy.com

Stacy Adams - SAW536 (Men's) - Chocolate
 

Stacy Adams - SAW536 (Men's) - Chocolate

$44.95

Buy at: Shoebuy.com

Stacy Adams - SAW536 (Men's) - Navy
 

Stacy Adams - SAW536 (Men's) - Navy

$44.95

Buy at: Shoebuy.com

Bailey Cashlux Fedora - The Benny
 

Bailey Cashlux Fedora - The Benny

$150.00

Buy at: Hartford York, Fine Hats & Accessories

The Bailey Delbert
 

The Bailey Delbert

$138.00

Buy at: Hartford York, Fine Hats & Accessories

Country Gentleman Hat, Newsboy 8 Quarter Cap
 

Country Gentleman Hat, Newsboy 8 Quarter Cap

$42.00

Buy at: macys.com

Wigens Newsboy Cap - The Patchwork Newsboy
 

Wigens Newsboy Cap - The Patchwork Newsboy

$125.00

Buy at: Hartford York, Fine Hats & Accessories

JB Stetson Wool Newsboy Cap - The Kennet
 

JB Stetson Wool Newsboy Cap - The Kennet

$150.00

Buy at: Hartford York, Fine Hats & Accessories

Wigens Newsboy Cap - The Elof M Patchwork Cap
 

Wigens Newsboy Cap - The Elof M Patchwork Cap

$90.00

Buy at: Hartford York, Fine Hats & Accessories

Borsalino Linen Newsboy Cap - The Luigi
 

Borsalino Linen Newsboy Cap - The Luigi

$125.00

Buy at: Hartford York, Fine Hats & Accessories

Durward Newsboy Cap
 

Durward Newsboy Cap

$63.00

Buy at: Hats.com

Men's Stetson Linen Newsboy Cap
 

Men's Stetson Linen Newsboy Cap

$65.00

Buy at: NORDSTROM.com

Scala Wool Felt Top Hat - The English Topper
 

Scala Wool Felt Top Hat - The English Topper

$85.00

Buy at: Hartford York, Fine Hats & Accessories

Scala Wool Felt Top Hat - The Mad Hatter
 

Scala Wool Felt Top Hat - The Mad Hatter

$95.00

Buy at: Hartford York, Fine Hats & Accessories

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About Debbie Sessions

Debbie Sessions is passionate about wearing history through fashion. She and her husband, Oscar, have turned their hobby into a career by teaching others how to re-create vintage style with affordable new vintage inspired clothing and accessories. We connect shoppers to the best vintage inspired clothing, shoes and accessories and teach fashion history as it was worn by everyday people. Need more help? Contact us anytime.

3 thoughts on “1920’s Mens Hats – Great Gatsby Hat Style

  1. Clate

    Ahh, thanks for that picture from 1927 of the gentleman with the Optimo Panama Hat. As much as I love boaters they don’t quite look right on my face, and Optimos are–well, optimal, for me.

    Seriously, though, I’m thinking of wearing one to a 1920’s event this summer, and even though I know there will be more boaters, and some will no doubt think I’m not getting it right, or that Optimos are more of an early 1930’s thing, I now know that it is “correct” in its own way. Maybe they were actually considered more casual or trend-setting, who knows–

    Thanks so much!

    Reply
    1. Debbie Sessions Post author

      Optimo hats were usually a wealthy mans hat while the boater could be a cheap/throw away type. Wearing an Optimo would certainly make you a more sophisticated gentlemen. Good choice!

      Reply
  2. Clate

    Thank you so much! had wondered about the initial “status” of Optimos, in contrast to the seemingly ubiquitous boaters, during the 1920’s.

    I will say one other thing, and that is, thankfully, I am not as elderly as the gentleman in the photo–for a while yet, anyway.

    Kind regards.

    Reply

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