From Mob Job to Hob Knob, Gangster Hats Ooze Confidence

Gangster Fedora Hats

As Jay-Z croons in his song In My Fedora, “I’ve got that girl that I adora, while I’m chilling in my fedora, who says a gentleman can’t have swag?”

The mens fedora is synonymous with “gangsta swag” and it’s no wonder.

From Al Capone to rappers like Da Baby, original and modern-day gangsters have been rocking fedoras throughout the ages. And while it is as essential part of any mobster’s wardrobe, they’ve since crossed over into the mainstream.

Jay-Z in a straw fedora. Photo by Frank Micelotta/Getty Images)
Jay-Z in a straw fedora with a classic teardrop pinched crown at the MTV Video Music Awards in Miami, Florida (Photo by Frank Micelotta/Getty Images)

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NEW YORK, NEW YORK – SEPTEMBER 11: Chosen Wilkins attends the front row for Global Fashion Collective I during NYFW: The Shows on September 11, 2021 in New York City. (Photo by John Lamparski/Getty Images for NYFW: The Shows)

This old school pinched crown chapeau has crossed over into the mainstream. Contemporary fashion visionaries have cemented this hat’s place as more than an authoritative accent to a fresh pressed mafia style suit. Mens fedoras are anything but one size fits all.

Read on to learn about the original, impressive and trendy wise guy accessory, where it started, and how it’s changed over the years.

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VENICE, ITALY – Rosa Perrotta is seen arriving at the 77th Venice Film Festival in a women’s felt hat. This is the type of head piece actress Sarah Jessica Parker would have worn as one of Carrie Bradshaw’s Sex and the City Hats. (Photo by Daniele Venturelli/WireImage)
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ATLANTA, GEORGIA – AUGUST 05: Lu attends “Brat Loves Judy” WE tv watch party at Views Bar and Grill Atlanta on August 05, 2021 in Atlanta, Georgia. (Photo by Paras Griffin/WireImage)

The Perennial Gangster Hat

No hat has stood the test of time like this one. Its story cannot be told without mentioning some of the world’s most notorious bad boys.

There’s something about bad boys that America and fashion love. Perhaps it’s their wild lifestyles, their unflappable confidence or all their money.

Psychologists say it’s because inside us all is our own “bad side,” making these characters relatable in some way. 

But whatever it is, the masses have been idealizing gangsters, and their styles, since the Great Gatsby roaring 20s – gangsta hats and all. And movies featuring mob bosses have made this hat style part accessory, part costumer, and part prop.

Think of Robert De Niro in The Godfather or Tom Hanks in the Road to Perdition. What do you see in these famous, based-on-real-life crime movies – that’s right…the same hat. Like the mob bosses who wore them in the 1920s, a fedora is much more than just a men’s felt hat. It’s a sort of kingmaker crown.

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NEW YORK – 1974: Robert De Niro performs a scene in The Godfather Part II directed by Francis Ford Coppola in 1974 in New York, New York. (Photo by Michael Ochs Archive/Getty Images)

Troy Roberts, store manager at Goorin Bros. Hat Shop on Melrose in L.A., said it was America’s original outlaws that started this fashion trend early on. Their prominence in film noir propelled these hat from their heads of actors to the likes of us all. 

“It was that typical prohibition-era, mafia-style, mob look, and it later became popular in the country and got attached to an aesthetic,” he explains. 

These are not 1920s era hats. In fact, this evocative aesthetic should be attributed to the mafiasos in the 1930s 1940s. Here’s Frank Carbo and Irving Wexler, seen sporting hats with traditional brims and teardrop crowns, albeit Carbo’s has a wider black hat band.

Frank Carbo. Photo by Pictorial Parade/Hulton Archive/Getty Images)
Sporting the classic 2-inch brim gangster hat seen here is Frank Carbo, a boxing manager and gangster photographed in 1936. Frank was a gunman for Murder, Inc., a dominant organized crime group in New York City. Photo by Pictorial Parade/Hulton Archive/Getty Images).

These mobsters made headlines for their extracurricular affairs, known for Prohibition Era bootlegging, rum running, prostitution and gambling. Their adoption by mobsters inspired their use in gangster movies.

Waxey Gordon\'s in 20s era fedora with a pointed crown. (Photo by Archive Photos/Getty Images)
Circa 1933: A photograph of Jewish-American gangster Irving Wexler, aka Waxey Gordon, who was a rum runner bootlegger during the Prohibition Era. Seen here wearing a classic men\’s gangster hat with a more pointed, tear shaped brim then popular women\’s fedora hats worn today.(Photo by Archive Photos/Getty Images)

Equal Rights Hat

While real life bandits sparked this hat’s popularity, it was actress Sarah Bernhardt who made it a popular female accessory. According to History of Hats, Bernhardt gets the credit for unveiling the look in the Italian film drama Fedora.

Sarah Bernhardt and her grand-daughter in sun hats. (Photo by Hulton Archive/Getty Images)
French Actress Sarah Bernhardt (born Henriette Rosine Bernard, 1844 – 1923) and her grand-daughter in sun hats. (Photo by Hulton Archive/Getty Images)

Sarah Bernhardt and granddaughter vamping in decorated women’s sun hats.

But in America, fedoras were associated with the male-dominated mob scene, until the 1960s. The fedora, like most fashion trends, is no longer gender specific. We’ve seen them on female celebrities like Madonna, Britney Spears, Lindsay Lohan and more. 

Feminists take note.

But adopting a male hat style and making it unisex, the look went on to become an emblem of the women’s liberation movement. Today, it’s a gender fluid hat style.

Roberts says women’s fedoras hats sell more than men these days. “I always say that any hat can be a woman’s hat. In the past, the fedora has been attributed to men, so it’s very cool to see women wearing them now,” he said. 

And like the people who can pull this hat style off has evolved over the years, so have their shapes, sizes and millinery. 

Fedora Restora

Hat shop owner John Bryan says the flat brim style of these Italian-named toppers has changed a little throughout history. But this hat’s popularity has surged in a big way.

“When people think of a fedora, they think of the hat. But the word ‘fedora’ is actually Italian for ‘divine gift.’” he said. “Any hat could, technically, be a fedora, a divine gift.”

But today everyone associates this word with the popular mafioso style hat with the crushable tear dropped crown, with some caveats. 

Then, by the 1960s, the hat had changed, along with its clientele. No longer just for men, the hat style itself evolved and become among the most popular women’s felt hat. But women’s styles were a bit different. The brim went from 2 inches to 2.5 inches.

“It was that Mad Men look,’” Bryant explained. It’s not fedoras either. Men’s felt hat styles have changes in many unexpected ways.

Bryant is referring to the popular television series centering around an advertising agency and its cast of money-driven, sex-obsessed, male and female industry leaders. Not necessarily gangster, but certainly they had some “bad” characteristics. Maybe that’s what the hat is all about – a symbol for pushing the boundaries.

Gangster Girls

Vicki Hodges in a gangster style wide brimmed fedora. (Photo by M. McKeown/Express/Hulton Archive/Getty Images)
Women’s fedora hats typically have wider brims. This gangster style pin stripe suit get up worn in 1972 by Vicki Hodge, a model and actress, features a women\’s felt fedora with a 2.5 inch fedora. (Photo by M. McKeown/Express/Hulton Archive/Getty Images)

The new and improved fedora came to a pop culture status and changed in design each decade. In the sixties, women’s fedora hats came into their own.

Bryant says at one point brims shrunk to 1.5 inches. Now the longer 2 to 2.5 inch brims are back as more people want the hats that can provide shade protection sun. Feminine styles have a taller crown and wider brim, like this one worn by Vicki Hodge in 1972.

As the width of the brim changed over the years, so did the materials they’re made from. The classic Manhattan black fedoras were felt. Today, you can find these hats made from leather, to animal hides, to fur, to straw. From asymmetrical brims, bright colors, patterns, and more, this is a hat that has a look to suit men’s and women’s styles. 

Today’s Fedora

Today the fedora is not just for classy Italians like Frank Sinatra and the Rat Pack. Acclaimed gangster rappers like 2pac and Biggie Smalls used fedoras to bring out their inner gangster at red carpet arrivals. But you don’t have to be a bad boy to pull off this trendy look. Tastemakers are wearing fedoras with sweaters, dresses, boots, and jeans. 

American rapper Notorious BIG in gangster fedora with brim flipped down. (Photo by Larry Busacca/WireImage)
American rapper Notorious BIG in a classic gangster fedora hat with the brim flipped down bucket hat style, flashing his bling at the 1995 Billboard Music Award. (Photo by Larry Busacca/WireImage)

Gangster hats are a great way to stand out from the crowd. Those with natural, curly hair should look for fedoras with a satin lining to keep their hair from drying and frizzing out. But be careful of bright-colored varieties, which can look like costume accessories or party hats.

Don’t cheap out. A good hat is a worthy investment that can last a lifetime. If you try to cut corners you’ll be disappointed. Cheaper hats fall apart. Inspect the inner lining, the underbrim, the hat band and the trim, which are all excellent barometer for quality.

The Hat Stops Here

Don’t get us wrong. We agree that fedoras remain gangster stylish. But you don’t have to be mob boss to feel like one. The fedora is a classic hat that’s clean, definitive, and powerful. If you’re on the fence about whether you have the inner outlaw to pull off a gangster hat, remember these trends. That way you know how to wear them, when to wear them, and what to wear them with. And you’ll also know how to borrow a dash of confidence and conviction from this legendary hat style.

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