Through the Decades: Men’s Hats

The weather is becoming warmer here in the Pacific Northwest, and what better accessory to block the bright sunshine than a hat? This week we are focusing on the main styles of men’s hats and how they came to be.

Most all hat styles that we know today, were designed and created between the 1920s and 50s, as that is when they were high in style and frequently worn.


In the 1920s, men’s hat styles varied according to the season. Hats were worn all year any time and any place. Warm spring and summer brought out Panamas, Boaters, and linen flat caps. Whereas the cooler fall and winter seasons brought out Derbies, Fedoras, and Bowlers to tie in better with their suits.

The Panama: Very light, hand-woven South American reed straw hat. The hat expressed a flexible design, which made it easy to fold up into a pocket during travel. There were two main types; Telescope Crown which represented more of a boater style, and Optima style which had a rolled crease down the center. Authentic Panama hats of any style were quite expensive so only the elite who traveled often typically purchased and wore them.

The Boater: Outdoor sporting became the new hobby for men (tennis, bike riding, boating) and with it came the Boater hat. Also known as the Skimmer straw hat, it was hand woven with thick straw with a 2 or 3 inch brim. A solid or striped ribbon around the base was often seen on boater hats. College students of the time often wore boaters with the ribbon showing off their school colors.

The Flat Cap: This cap is often recognized as the “Great Gatsby” hat. The Flat Cap is made of 8 triangle panels that meet at the top and are covered with a button in the same material. There is a small brim that the top rests on. They were typically made with light colored linen or cotton and lined in silk. In winter, they often came in tweed, wool, or even corduroy and in plaid or dark colored print. All classes sported flat caps as it was known as the working man’s hat. For drivers it was ideal as the lack of stiff crown helped it to not bump into the car roof when worn. It still remains a commonly worn hat for golf and other outdoor sporting events today.

The Derby/Bowler: This hat stemmed from a man who had developed it for riding, in particular, to protect the head from bushes and branches. Later, it became a popular hat for men who didn’t own horses.  The edges were  often curled around and finished with matching ribbon and the hat was overall made with lighter weight felt. This was the most common hat of the early 1920s and was often worn in black. In close relation to this hat was the Homburg hat which looked almost identical except for the crease down the middle.

The Fedora: This style of hat, also called a Trilby, features a wide 3 inch brim. Traditionally, brims would turn up on one side and down on the other, but the brim of the Fedora was shaped downward on both the front and back sides, making it roll slightly upward. Back then, young men called it the “snap brim” or “swagger hat” style. They also had a sharp crease down the middle that could be single or triangle shaped. The felt Fedora started as a middle class hat, but later the wealthy often associated it with prohibition and crime, as Al Capone was iconic for wearing this type of hat in the 1920s.

The Top Hat: The best hat for formal wear was most definitely the mid height beaver fur or silk top hat. The mid height beaver fur or silk Top hat with curled brim was still the best hat for formal wear in the 1920’s. Wearing a silk top hat was something only done at weddings or grand opera performances, where men in cheaper seats used collapsible silk top hats they could tuck under their seats instead.


The 1930s carried on all of the styles of the 20s, particularly the boater, fedora, derby and flat cap, as well as the infamous Walking hat.

The Walking Hat: Also known as the tweed hat or bucket hat. This style of hat was made of tweed and typically came in check or plaid patterns. Its brim was wide and turned down. It had an unstructured crown that was rounded typically without creasing and a thin fabric band with a flat bow.


In the 1940s, the fedora, Homburg and flat caps were still worn but only with certain styles. Hats were commonly worn tilted to the side during this time period. Brims took on many shapes and the back brim typically curved upwards. The new hat that stayed prominent throughout the 40s and into the 50s was the Porkpie.

The Porkpie: This hat was made of fur felt and was short with an oval top and deep crease around the oval top. It typically was worn in black or brown. The wide brim was curled up and sported a thin leather band that matched the color of the hat or had a wide ribbon with a flat bow. This hat was most often worn at an angle.

The 1950’s were a great time for men’s hats. By then, almost two decades of hat styles had gone by with little change in variety or design. The ’50s came rolling in with splashes of color and fun new designs. Unfortunately, the ’50s also were the last decade of men wearing hats being a required and expected fashion.

Straw hats were all the rage. Many of the traditional hat styles such as the porkpie, fedora, boater and more regained popularity with straw material. Bold and colorful as well as striped checked and geometric print hat bands were also added to them to match the colorful suits that men were commonly wearing.


By the 1960s, hat wearing for men was reaching an unfortunate decline, but the straw hat styles of the 50s remained the styles being worn and still prominent today!

Slouch hats or wide brimmed casual hats became popular in the 1970s. Fedoras also made a slight appearance again during this time.

In the 1980s, baseball caps in bright and/or bold colors and prints were frequently worn. Also caps that featured favorite sports teams or a variety of other sayings.


Here at Most Everything vintage, we have quite the variety of men’s hats including vintage style hats locally made by our milliner Babette’s Hatworks! Have a special style, color or size in mind? A custom hat can be made for you. Come check them out today!

Thanks for reading!


(All Research from the following:,,,,,


Categories: Features by SarahTags: , , , , , , , , , ,

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