The most iconic hat from the decade you were born

First lady Jackie Kennedy wears her iconic pillbox hat.

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First lady Jackie Kennedy wears her iconic pillbox hat.
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Art Rickerby/The LIFE Picture Collection/Getty Images

  • Hats have been part of our lives for thousands of years, and have been both functional and fashionable.
  • Over the past 100 years, hats have changed quite a bit, from the pork pie hat to the trucker cap.
  • Hats were often popularized by the famous people wearing them, as in the case of Frank Sinatra and the fedora.

If you take a look around outside, you’d probably see more than a fair few people wearing hats, whether it’s to complete their look or to prevent their ears from freezing off.

Hats have become more fashionable and less functional throughout their history, and have also become much less ornamental.

Keep scrolling to check out the evolution of hats over the last 100 years.


Around 1910, men wore straw boater hats during the summer.

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Connie Mack, manager of Major League Baseball’s Philadelphia Athletics, in 1911.
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GHI/Universal History Archive via Getty Images

Boaters are essentially straw fedoras – a hat that will later appear on this list – that men and women wore during the summer to keep cool.

During the late 19th century, schools began requiring students to wear boater hats as part of their uniforms, especially in the UK. By World War I, these hats were inescapable.

It later became popular with barbershop quartets and vaudeville performers, as seen in “Chitty Chitty Bang Bang” which takes place in this era.


The 1920s were known for flappers — the cloche hat is one of the most important parts of that look.

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Film actress Esther Ralston in a flapper hat, a.k.a. a cloche.
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Bettmann/Getty Images

Cloche hats get their name from their shape – cloche is French for “bell.” It’s easy to see the resemblance.

According to “The Fairchild Dictionary of Fashion,” a cloche is a “Deep-crowned hat with [a] very narrow brim or brimless, fit[s] head closely, almost conceal[s] all of the hair. Worn pulled down almost to eyebrows,” and hit the height of their popularity in the ’20s, though they did have a resurgence in the 1960s.


Silent film star Buster Keaton popularized the pork pie hat in the 1930s.

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Keaton in his signature pork pie hat.
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John Springer Collection/CORBIS/Corbis via Getty Images

Keaton started wearing his pork pie in the ’20s, and the next decade the hat was all the rage. According to Realize Magazine, the hat reached its peak in popularity during the Great Depression, which lasted from 1929 to 1939.

You might be wondering, why is it called a pork pie? Well, very simply, it’s because they look like pork pies! The flat top that’s pinched around the rim looks eerily similar to the crust of a pork pie.

Even though they might seem like old hat (literally), pork pies are probably best known now as the hat of choice for meth cooker extraordinaire Walter White/Heisenberg from “Breaking Bad.”


Cartwheel hats were the hat of choice for women in the 1940s.

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A woman rocking a cartwheel hat in 1948.
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Nina Leen/The LIFE Picture Collection/Getty Images

Cartwheel hats were first worn in the early 1900s, resurfaced in the ’30s, and then had their final resurgence in popularity during the ’40s and ’50s.

They get their name from their resemblance to actual cart wheels, which isn’t visible until the hat is worn at its traditional slanted angle. Essentially, you couldn’t wear them unless they were extremely tilted, because the brim was too wide to see out from underneath.


One of the most iconic hats of all time, the fedora, hit its stride in the ’50s.

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Frank Sinatra dons his signature fedora.
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Bettmann/Getty Images

Even though they’re associated with wannabe hipsters now, fedoras, defined as a felt hat with “a wide brim, crown that is indented and pitched, and a ribbon,” used to be the pinnacle of fashion a few decades ago.

After years of use, the fedora became associated with ’50s icons like Frank Sinatra, Humphrey Bogart, noir films, and gangsters, all of which were (and are?) definitely considered cool.


Former first lady Jackie Kennedy popularized the pillbox hat in the 1960s.

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Jackie Kennedy in a pillbox hat in July 1960.
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Paul Schutzer/The LIFE Picture Collection/Getty Images

In fact, Kennedy made the pillbox hat one of the most iconic hats of all time as she was wearing one when her husband, President John F. Kennedy, was assasinated.

According to Fashion Encyclopedia, pillbox hats were first popular in the ’30s but reached the apex of their popularity in 1961 at President Kennedy’s inauguration, when the first lady wore one. She continued to wear them throughout his presidency.

The name originates from the hat’s resemblance to pill containers, with its straight sides, flat top, and no brim.


The hippie movement was well absorbed into popular culture in the ’70s, and fashion was no exception, as seen by the rise of the floppy hat.

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French actress Brigitte Bardot on August 4, 1972.
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AFP/Getty Images

Iconic actress Brigitte Bardot was known for her signature floppy hats. Before this, hats were generally very rigid and on the smaller side, with the exception of cartwheel hats, which were huge but still not floppy.

Nowadays we can see that the floppy hat perfectly encapsulates the decade of the ’70s, which is also famous for other free-flowing, flexible pieces of clothing including bell bottoms and bell sleeves.


Bucket hats are the quintessential ’80s headwear.

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LL Cool J in July 1987.
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Paul Natkin/Getty Images

LL Cool J and the hip hop community seized the opportunity to make bucket hats trendy again after years of being associated with “Gilligan’s Island.” Originally, the bucket hat was used by fisherman and other outdoorsy people to keep both rain and sun out of their eyes, plus they’re easily foldable.

The “Mama Said Knock You Out” rapper, the Sugar Hill Gang, and Run DMC were all frequently spotted in the ’80s sporting bucket hats.


Steampunk fashion returned with a vengeance in the ’90s, hats included.

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Linda Perry of 4 Non Blondes in December 1993.
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Ron Galella, Ltd./WireImage/Getty Images

Daily Dot defines steampunk fashion as “a retrofuturistic mashup between a Victorian aesthetic and cyberpunk.” In essence, it combines machinery and fashion, making for some truly interesting clothing and accessories.

Linda Perry, a ’90s fashion icon, frequently wore a steampunk hat that looked like a top hat combined with metalworking goggles – even if she didn’t realize it at the time.

The look has become so iconic and synonymous with Perry that it’s a popular Halloween costume.


Trucker hats embellished with rhinestones and designs were the cap of choice during the early 2000s.

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Ashley Tisdale in 2006.
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Jon Kopaloff/FilmMagic/Getty Images

Historically speaking, the aughts were a rough time for fashion, and headwear was no exception. Socialites like Paris Hilton and Nicole Richie paid big bucks to wear simple trucker hats with the brand names Von Dutch or Ed Hardy emblazoned on the front, and that’s it … Nothing else made these hats particularly special.

We’ve since given up this form of the baseball cap, and replaced it with the “dad cap,” though if the Jenner sisters have their way, Von Dutch is on its way back.


This past decade has been characterized by the resurgence of a hipster favorite, the beanie.

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Cole Sprouse wearing Jughead’s iconic beanie in “Riverdale.”
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The CW

Beanies were popular in the ’90s, but over the past nine years, they’ve skyrocketed in popularity again as every self-styled hipster has rocked a slouchy beanie over their bedhead.

Jian DeLeon, editor of Highsnobiety, explained the appeal of a beanie to Vox in September 2018. Beanies “are supposed to convey this semi-stoner, relaxed, California ‘bro’ type,” DeLeon said.

The easiest way to see how prevalent the beanie has become is to check out an episode of “Riverdale,” which has become teen royalty. The show is based on characters from Archie Comics which debuted in the 1940s.

When “Riverdale” updated its characters, it took Jughead Jones and his omnipresent crown, and turned him into a hipster, beanie-wearing, brooding writer. It can’t get any more 2010s than that …

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