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What is a Pillbox Hat? Types, Definition & Photos

Strap in and take a close look at the pillbox hat, where has it been in history, who wore it in history, what industry uses them, how to properly wear them and their comeback in fashion.

A close look at a woman wearing a black leather jacket and a black pillbox hat.

I was a dedicated vintage clothing devotee in my teenage years when it was not yet fashionable to scour through thrift stores for iconic fashion accessories. I vividly recall the sensation of wearing my first retro hat, with its mysterious veil, which in my hormone-ridden teenaged brain rendered an utterly romantic look. Although, back then, I did not know what a pillbox hat was.

Milliners named the pillbox hat after small pill dispensers. It is a small, elegantly designed round and brimless women’s hat with straight sides and a flat crown. Crafted of various materials in solid colors and accessorized by a single jewel, pin, or a colored veil.

The pillbox hat might seem insignificant. However, I discovered it has a long and fascinating history that tells the story of great civilizations and the men and women who embraced the pillbox hat for various reasons – so read on!

What Are the Origins of The Pillbox Hat?

This is a vintage blue pillbox hat with netting.

The iconic pillbox hat has a long and illustrious history dating back to the end of the Roman Empire when Roman soldiers wore pileus hats similar to contemporary pillbox hats we have come to know.

Pillbox hats subsequently became fashionable in military units across the globe and throughout history and are still in use today as an integral part of the Royal Millenary College in Canada’s dress uniform for formal occasions.

Women adopted the pillbox hat during Medieval times, initially as bridal wear. The pillbox hat has evolved into standard bridal attire crafted from luxurious silk or felt and accessorized with a fine French veil.

The contemporary pillbox hat as we know it today started making a significant appearance in the 1930s when Milliners designed pillbox hats crafted from various materials ranging from velvet, wool, and organdy to leopard skin. They must have been on to something as pillbox hats became “quite the rage” due to their simple yet elegant designs.

The Iconic Fashionistas Who Made the Pillbox a Must-Have Item

This is a close look at a woman wearing a vintage 1920s attire with a pillbox hat.

While Pillbox hats were still fashionable in the 1940s, Dior’s Parisian “New Look,” epitomized by its feminine designs and wide-brimmed hats, held sway during that era and well into the 1950s.

A then little-known presidential first lady,  Jacqueline Kennedy Onassis, or “Jackie O,” upped the fashion stakes by wearing a custom-made pillbox hat to her husband’s inauguration in 1961.

The former first lady was the epitome of glamorous style in the 1960s, with her fashion first trademarked oversized sunglasses and bouffant hairstyles. However, nothing is as emblematic of that era as Jackie O’s classic pillbox hat that launched an iconic fashion statement from the 60s to this day.

The renowned Roy Holston Frowick (Holston) designed Jackie’s pillbox hat. During an interview, Holston informed the media that his original design did not look as it was supposed to when he initially created it.

According to Holston, Jackie’s pillbox hat was too small for her during her pre-inaugural fitting, but she insisted on wearing it anyway.

The classic Jackie O pillbox look was born due to a random act of nature. During JFK’s inauguration, a forceful gust of wind threatened to dislodge her pillbox hat, so the former first lady held on to it and dented it as a result.

Hat makers subsequently copied Jackie O’s famous pillbox hat so extensively that all the replicated versions had dents in them. Many other celebrities adopted Jackie O’s fashion signature.

Audrey Hepburn was another iconic fashionista who fully embraced Jackie O’s pillbox hat style, although in a bolder style and with a mysterious veil.

Why Did the Pillbox Hat Go Out of Fashion?

This is a woman wearing a vintage pink pillbox hat with netting.

During World War 2, women could often not wear hats as fabrics, as with so many other raw materials, were rationed at the time. Therefore, the pillbox hat was rarely worn and only on formal occasions.

Men started emulating John F Kennedy, who did not wear a hat at his inauguration in 1961, and women mostly followed suit, except for Jackie O’s pillbox hat.

It was not deemed fashionable to wear hats in popular culture, as made evident by the famous Beatles and the model Twiggy renowned for wearing outrageously short miniskirts.

Nobody on the film set of “Star Trek” wore hats, except for the episode featuring President Lincoln.  Another reason for the hat’s decline in popularity could be attributed to the Catholic Church’s decision in 1967 to no longer require women to wear hats in church services.

Women were also less inclined to wearing pillbox hats when fashion magazines marketed dandruff shampoo. Advances in plumbing also meant that women no longer needed to use water barrels for washing their hair.

According to the influential Women’s Wear Daily, better quality shampoos and conditioners also meant that women did not have to hide greasy hair any longer.

In the 1960s, women would still wear hats to formal occasions and church services. It was primarily elderly ladies who would sport a hat and gloves to shop at their local grocery store.

Young women tended to steer away from wearing hats, except for the trendy pillbox hat, the fashion rage throughout the 60s.

During the 1970s, hats went out of style due to the London Mod look, emulating the Beatles and Mary Quant’s fashion statements. When the Woodstock era arrived, calico dresses, peace signs, and combat boots without hats were in style.

Young, progressive people thought hats were outdated and best suited to grumpy conservative older men and dowdy grannies. It was customary for men to tip their hats to mature women who still wore their traditional hats and glove attire during that time.

The Millennial Pillbox Hat Vintage Revival

This is a woman wearing a classic stewardess uniform with a pillbox hat.

For the next three decades, pillbox hats were not generally regarded as trendy by young people until Generation Y or Millennials embraced hats as they were seen as hip and happening accessories.

It became fashionable to scour vintage clothing stores, which also inspired forward-thinking designers to craft new hats.

Millennials have invigorated life into old pillbox hats by combining them with all kinds of clothing like vintage jeans and formal outfits, thereby creating a whole new fashion signature by making it their own.

Celebrities such as the Kardashians and Madonna have worn pillbox hats and made it a must-have fashion accessory.

Hats have made a big come-back, and your grandmother’s pillbox hat is no exception. In present times they are ubiquitous, most notably in online shops and blogs dedicated to hats. This hat obsession has also led to renowned milliners who now design bespoke hats for celebrities like Lady Gaga and Paris Hilton.

Many other modern-day celebrities have revived the vintage pillbox hat after its forty-year slumber.

How To Replicate the Pillbox Hat Look In 2021?

This is a close look at a woman wearing a brown pillbox hat with her button shirt.

Are you feeling inspired to rock a one-of-a-kind vintage pillbox hat? Look no further!

There are numerous places where you can find retro pillbox hats raging from flea markets, yard sales, including vintage or thrift stores.

Online shops are also a great option, especially if you want to stay away from crowds. I suggest that you Google “vintage pillbox hats to see what’s on the market – the results might be pleasantly surprising!

Another option is to buy a newly produced pillbox hat from a countless array of leading hat designers. However, the downside is that new hats tend to be more expensive than their authentic “cousins,” and you will not experience the sheer delight of finding a beautiful vintage pillbox hat with a unique history behind it.

Other great online options are Etsy, Goodwill, thredUP, or eBay for vintage treasures. Interestingly a large majority of traditional vintage shop owners have started to market their items on the likes of Etsy.

If all else fails, scour your grandmother’s attic, as there’s a great chance that she might have a beloved pillbox hat hidden away in a chest of drawers.

It is plain to see that the elegant pillbox hat is a classic which will never go out of style.


In a world obsessed with fast fashion and staying up to date with the latest trends – the pillbox hat evokes great nostalgia for an era when life’s pace was slower and women had time to dress in their finest attire.

The pillbox hat exemplifies the life and times of so many great men and women throughout history, from Roman battlefields to the contemporary hip young women we know today. May it have a long and illustrious reign!  


Stiletto City: How to Wear a Pillbox Hat

Easy Hat Blocks: Pillbox Hats Short History

Encyclopedia: Pillbox Hats

Bellatory: Vintage Pillbox Hats and the Women Who Wear Them

Quora: When Did Wearing Hats Fall Out of Fashion

Pop Sugar: Jackie Kennedy Halston Pillbox Hat