To describe a straw boater hat, you have to embrace what it isn’t. It’s a fedora, but not quite. Its brim is trimmer and tighter than a fedora. It’s a bowler hat, but not quite. A boater hat doesn’t have that pleasantly domed top and, instead, traditionally features a folded or flat, smooth top.
That “but not quite” is the important part. Because it’s exactly how you’d describe a boater hat wearer. The boater wearers aren’t trend chasers. They’re the ones who set the trends. They are committed to eccentricities, style-wise and otherwise. Bold and brave, this isn’t an accessory for a wall flower. This hat was made for spotlights, flashbulbs, and icons.
A boater hat is the sartorial equivalent of pineapple on pizza—it’s not for everyone but damn, it is delicious on the right person.
Women’s Boater Hats
Women’s boater hats are distinctly feminine, but remain as firmly innovative as their male counterparts. Taylor Swift used the boater hat as a bridge between her country style era into her modern, hipper vibe both sartorially and musically. Fellow trendsetting singer Janelle Monáe brought street style coolness to the red carpet with her love of boater hats. For her part, Princess Diana—the royal outsider—elevated the boater with luxurious details to make it her own: elegant and tasteful, but still cooler than the stiffly worn hats perched on the heads of other aristocrats.
This is what we call the boater hat trick.
Boater Hats vs Pork Pies
While boaters and pork pies are both available as straw hats for women, they are also a little different from erach other. Chances are, you’ve seen the pork pie on an icon or two. The hat, named for its uncanny resemblance to the traditional English meat pie, has been around since the 1800s but it was silent film actor Buster Keaton who brought men’s pork pie hats back from the depths of fashion obscurity in the 1920s.
It was a practical choice for Keaton (pictured below in a scene from the 1924 film ‘The Navigator’). The movie star did his own stunts and specialized in physical comedy paired with a deadpan expression. Those flimsy straw boaters that gentlemen favored at the time were too fragile for the intense slapstick Keaton relied on, so he turned to more durable pork pie hats to innovate. The Hollywood icon estimated that he wore thousands of versions of his signature pork pie hat throughout his career.
Fast-forward a few decades later and pork pies were adopted by the cool jazz cats that hung out in smokey clubs with sticky tables. The pork pie hat became saxophonist and clarinetist Lester Young’s signature style so much so that after his death in 1959, legendary bassist and bandleader Charles Mingus composed an elegy for him called Goodbye Pork Pie Hat. That’s how this style became what cats call the New Orleans jazz hat.
Fast-forward again a few decades and the boater hats again emerged on the heads of a new generation of offbeat musicians: this time it was the rude boys of 1980’s and 1990’s ska bands.
The boater morphed into even more of an eccentric accessory then they already were, taking on brightly colored feathers in their brims, boldly patterned hat bands, or even all-over checkerboard patterns. Chris Foreman, pictured above performing in Nottingham in 2012 with his band Madness, demonstrates how serious the ska scene got about their men’s boater hats.
1. Taylor’s Hipster-Chic Black Felt Pork Pie
In 2014, pop-country princess Taylor Swift overhauled her life. She moved away from her home in Nashville, relocating north to New York City. She moved away from her signature musical style too, dropping the country component completely in favor of the synth-pop and dreamy overlapping vocals of her 1989 era. It was a huge change for the superstar.
“I was so intimidated by this city for so long,” she told Rolling Stone, “I thought I would never be able to make it here, because I wasn’t something enough—bold enough, brave enough to take on this huge city in all of its blaring honesty. And then at a certain point I just thought, ‘I’m ready.’” And that massive life change came with a new favorite accessory. Taylor Swift was suddenly the darling of NYC, photographed everywhere with her new signature pork pie hat.
Why It Works
Taylor’s pork pie hat was transformative, a metaphor for her new era of music and new life. It was the hip bridge that linked her twee, sweet Nashville style to a much cooler, much more mature New York City style. She kept her country-sweet dresses, chicly tailored coats, and lady-like bags, but when paired with an ultra-hip pork pie hat, the vibe was suddenly sophisticated and worldly. Much like Buster Keaton, Swift understood the transformative power that comes with a pork pie hat.
How to Wear It
Every woman should own a pork pie for those days you just need to make a splash, take it from Taylor. The pork pie hat can top any fit to make it suddenly more interesting. Taylor’s pretty sundresses, tailored shorts, and youthful knee-high socks from her mid-2000s Soho strolls could be too sweet, but the addition of a pork pie topper takes her wardrobe directly into cool girl territory.
2. Janelle Monáe’s Avant-Garde Pork Pie
Once again, we’re applauding a women’s pork pie on a statement-making musician. This time, it’s Grammy nominated singer and actress Janelle Monáe’s bold and brilliant style. Monáe’s music doesn’t shy away from anything—high-art concepts, sociopolitical statements, deeply rooted mythos around a robotic alter-ego—and her wardrobe is just as compelling and bold.
Why It Works
For Monáe the modern pork pie hat is a gasp-worthy icon, an accessory made for making statements which suits her, since her public persona is that of a modern dandy.
Remember: in the mid-2000s, no one was wearing hats on the red carpet, let alone women. Monáe pushed past all those ballgowns and basic LBDs to usher her new era of style: avant-garde couture, traditional masculine suiting tailored precisely, and (of course) a signature sharp and cool hat to top it all off. “When it comes to music, I consider myself a time traveler,” she once told Vogue, and we have to believe this persona extends to her fashion as well. Part traditional, part ultra-futuristic, and always topped with a really stylish hat.
How to Wear It
Of course the rapper/author/singer/actress/producer/model would want a hat that’s equally multi-talented as she is. Janelle Monáe understands that pork pie hats are as versatile as you are.
Monáe’s pork pie hats belong on red carpets just as much as they belong on sidewalks. Dress it up with, like she does, in (her signature) black and white tuxedo palette and avante-garde fits or dress it down with cool streetwear and cutely coiffed hair.
Either way you wear it, the superstar aura will follow the pork pie.
3. Princess Diana’s Elegant Pork Pie
How posh can the pork pie go? Proper posh.
The Royal Family’s hat-wearing obligations are so plentiful that it was almost inevitable that Princess Diana would eventually get around to trying a pork pie hat. The masterful way the Princess of Wales elevated the pork pie hat to luxury levels—that’s the real magic. Rendered in velvet, veiled with birdcage netting, or saturated in the richest jewel-toned colors, Princess Diana brought women’s pork pie hats out of the ska mosh pits and made them aristocratic.
Why It Works
The People’s Princess, a major innovator herself, plucked the pork pie hat from the heads of cool musicians and brought it up to royal standards. The results? A melding of hipness and exclusivity that is absolutely irresistible (and absolutely perfect for the trailblazing royal).
How to Wear It
Lady Di understood that the devil’s in the details. The Princess adorned her pork pie hats with lavish white bands. She’s proof that the pork pie can be elevated beyond dark smokey jazz clubs and sweaty music halls, all the way to Buckingham Palace.
The Hat Drops Here
Pork pie hats aren’t meant for the masses.
They don’t manifest patriotic, country-wide love like cowboy hats. They don’t telegraph the crisp, classic, timeless elegance of a fedora. No, pork pies are for the misfits. They’re for the off-beats. They’re for the night owls and the mavericks, the slightly strange, always wonderful artists and thinkers and vanguards. Let the rest of the crowd wear beanies and baseball hats: You’ve got more style than that.
Let’s celebrate that hip hat with the silly name and the innovators that are bold enough to wear it.