Playful Pop Princess: Why We Love Britney Spears Hats

Britney Spears Hats
The many hats of Britney Spears.

Britney Spears hats run the gamut from women’s cowboy hats to women’s fedoras to women’s leather top hats to women’s flat caps.

And there’s nothing we love talking about more than the spotlight and hats. It’s a match made in heaven, and make no mistake, Britney is both an angel and a hat person.

Britney Spears Top Hats

Britney Spears Top Hat at the Primary Action's and Adwil Agency's Emmy Suite - Day 2 at Liberace Penthouse in Beverly Hills, California, United States. (Photo by Alexandra Wyman/WireImage for Primary Action)
Britney Spears wearing South Paradiso Leather top hat with red braided leather hat band during Primary Action’s and Adwil Agency’s Emmy Suite in the Liberace Penthouse in Beverly Hills. (Alexandra Wyman/WireImage)


For someone whose life has been magnified by scrutiny and publicity, Britney has never been shy of rocking hats that are loud and proud.

Hats, as we all know, are strong giveaways of one’s fashion statement. We can tell a lot about any celebrity just by the type of toppers they choose to put on. That said, we’re ecstatic to show you more than a dozen head gears worn by the Princess of Pop throughout the years!

We start off the list with some of the most jubilant types of hats worn by Britney. Women’s leather top hats and cowboy hats are distinct in such a way that whoever wears them, literally, wants to be seen wearing them. Britney is no stranger to attracting attention, and with these head gears, she sure was to get a lot of that.

Singer Britney Spears poses with the trophy at the Bambi Awards 2008 on November 27, 2008, in Offenburg, Germany. (Photo by Patrik Stollarz/Getty Images)
Britney Spears in a classic silk top hat at the Bambi Awards in Offenburg, Germany. (Photo by Patrik Stollarz/Getty Images)


She sported a jet-black top hat with a feather band to pair with her all-black womanizer fishnet tights and see-through bodysuit. Oh, did we mention that she rocked this stunning fit as she received a Bambi Award for Best International Pop Star?

Recording artist Britney Spears performs onstage during the 2016 Billboard Music Awards at T-Mobile Arena on May 22, 2016, in Las Vegas, Nevada. (Photo by Kevin Winter/Getty Images)
Recording artist Britney Spears performs onstage in a red leather top hat the Billboard Music Awards in Las Vegas. (Photo by Kevin Winter/Getty Images)


Above, the multi-awarded artist shows off a fiery red leather top hat to match her blazing short dress, fishnet tights and thigh-high boots. Britney wowed the crowd with her very own medley hits as the opening act of the widely anticipated awards night.

Britney Spears Cowboy Hats

Off the stage, Britney is fond of wearing cool cowboy hats paired with her carefree style of outfits.

In one backstage interview, the singer has been spotted wearing a copper brown, women’s straw cowboy hat. With the side brims turned up, the hut-style design of this topper is a perfect complimentary piece for a rather silent off-white fur top.

Britney Spears Cowboy Hat seen at Primary Action's and Adwil Agency's Emmy Suite - Day 2 at Liberace Penthouse in Beverly Hills, California, United States. (Photo by Alexandra Wyman/WireImage for Primary Action)
Britney Spears in a distressed straw cowboy hat with a frayed brim at Primary Action’s and Adwil Agency’s Emmy Suite in the Liberace Penthouse in Beverly Hills. (Photo by Alexandra Wyman/WireImage for Primary Action)


The singer is happily seen wearing a winter wheat cowboy hat magnificently paired with a smooth cantaloupe dress. The contrast of the coarse texture of the topper from the silky feel of the dress must have felt as awesome as it looked. With that huge smile, where is the lie?

Britney Spears at the 2000 Billboard Music Awards in Las Vegas, Nevada. December 5, 2000. (Photo by Kevin Winter/ImageDirect)
Britney Spears at the Billboard Music Awards in an embroidered red women’s cowboy hat with an exotic feather plume. (Photo by Kevin Winter/ImageDirect)


Britney Spears Fedora Hats

At first glance, for an untrained set of eyes looking at headpieces, fedoras and trilby hats are often confused for one and the other.

For a quick comparison, a trilby hat is smaller and usually has a narrower brims than a fedora. Another defining feature of trilby hats is that they often have taller and pointier crowns compared to fedoras.

Yes, we know, it’s quite fascinating to differentiate the two. Interestingly though, Britney rocks either of these two just as well as the other!

Britney Spears performs on stage for MTV\'s
Britney Spears performing in a gray felt trilby with a black leather hat band at MTV’s TRL. (KMazur/WireImage)


In 2003, Britney sported a gray classic gangster hat with a black band, which was a sharp contrast to her playful hanging top. We’re living for the zipped leather pants that are just as daring as the whole combination of the outfit. Well, it’s Britney! She does what she wants, whenever she wants.

A lady’s black trilby elevates the simple yet elegant look that Britney is exuding. The wide brim of the topper is as noticeable as its pinch, and adds important details to perfect the look with the floral dress. Is it even Britney without the stunningly high matte boots?

Singer Britney Spears attends the MTV Bash at the Hollywood Palladium on June 28, 2003, in Hollywood, California. (Photo by Kevin Winter/Getty Images)

Singer Britney Spears attends the MTV Bash at the Hollywood Palladium on June 28, 2003, in Hollywood, California. (Photo by Kevin Winter/Getty Images)
Singer Britney Spears in a black trilby hat at the MTV Bash at the Hollywood Palladium on June 28, 2003, in Hollywood, California. (Photo by Kevin Winter/Getty Images)


On the other hand, the Princess of Pop effortlessly wears this trilby hat, which perfectly encapsulates all the descriptions we mentioned earlier. A narrow brim, a tall crown, a smiling Britney with her pearly whites, and her pearly necklace, too.

Britney Spears attends the grand opening of LAX Nightclub Las Vegas on August 31, 2007, in Las Vegas, Nevada. (Photo by Chris Weeks/WireImage)
Britney Spears in a straw trilby hat at LAX Nightclub in Las Vegas. (Chris Weeks/WireImage)


In contrast to that, this immaculate straw trilby hat with a simple black band casts a dreamy aura over that clean dress. Britney’s fair complexion and signature blonde look make her the perfect model for this cotton-made topper, which also has a playful side brim.

Britney Spears Caps

Over the years, Britney has also shown a relaxed and light persona that has endeared her to most of her followers. Through some of the caps that she has worn, she has contributed to making them fashionable and trendy. Britney’s contribution to popular culture all over the world is unfathomable.

Britney Spears is seen during MTV Mardi Gras 2002 at Jackson Square Park in New Orleans, Louisiana, United States. (Photo by KMazur/WireImage)
Britney Spears in a greek fisherman’s cap at the MTV Mardi Gras at Jackson Square in New Orleans. (Photo by KMazur/WireImage)


There’s nothing more that screams early 2000s Britney than this charcoal gray Greek fisherman cap with light gray strings. As an accessory to the denim jacket and floral shirt, the cap is fashionably relevant for an event in front of MTV’s bright lights.

Britney Spears during
Britney Spears in a pink leather cap at the “Crossroads” Hollywood Premiere at Grauman’s Chinese Theatre in Hollywood. (SGranitz/WireImage)


In another social event, the singer was pictured wearing a light pink leather cap paired with a simple pink dress. Coupled with a few accessories, Britney Spear’s pink hat fantastically got the job done. Leather cowboy hats have become quite the rage. JLo’s cowboy hat at the Met Gala was a real head turner.

As cliché as it may sound, there really is beauty in simplicity. And hey, Leonardo da Vinci once said, “Simplicity is the ultimate sophistication,” and no, we will not argue with a polymath.

Singer Britney Spears arrives at the 2002 MTV Video Music Awards at Radio City Music Hall on August 29, 2002, in New York City. (Photo by Mark Mainz/Getty Images)
Singer Britney Spears in a military cap at the MTV Video Music Awards at Radio City Music Hall, in New York City. (Mark Mainz/Getty Images)


We officially end this list with an iconic outfit from the Princess of Pop. She arrived at the 2002 MTV Video Music Awards in a black patent leather military cap to complete her dominatrix-esque look. Don’t forget that she also rocked a black leather dress and audaciously laced-up stilettos. Four words: Britney is a boss!

Here’s a little bonus for making it through all the amazing headpieces worn by Britney throughout the years.

Did you know that Britney also loves to sport some baseball caps too? We’ve all seen the Britney Spears Von Dutch Hat. But did you know she also wore this Ed Hardy baseball cap?

Britney Spears at an Ed Hardy event. (Photo by Alexandra Wyman/WireImage for Primary Action)
Britney Spears in an Ed Hardy hat with the patented skull logo of the fashion house. (Photo by Alexandra Wyman/WireImage for Primary Action)

Britney’s conservatorship and social media antics

And so from the fashionable hats and colorful caps, we cross over to some of the recent developments in the multi-awarded singer’s life.

Britney made headlines late last year when the #FreeBritney movement willfully trended over at social media spaces. Fans were behind the singer’s plea to end the then 13-year conservatorship arrangement with her own father, Jamie Spears.

Last November, a judge ruled in favor of Britney, and the conservatorship was eventually terminated. This led to the icon regaining most of her freedom, which for the longest time, was under the control of her conservators.

While we are happy that justice has prevailed for Britney, her cryptic Instagram are unsettling. And yeah, the risqué photos, are probably a little too risqué.

Celebrity pundits have speculated that most of the cryptic posts are silent tirades against the Spears’ family, particularly towards her younger sister, Jamie Lynn.

Safe to say, you can color us worried, as we hope that things get better for their estate in the near future. Some good news though! 

Britney and her fiancé, actor and fitness guru Sam Asghari got engaged last September, and have reportedly been busy planning their wedding. The pop star seems to be enjoying the taste of renewed freedom, and we’re here for anything that has to do with #FreedBritney.

Lucky: The Hat Drops Here

Britney Spears truly is an influential pop icon, who has brought music to life especially during the early 2000s.

The stories from all these hats mirror who Britney is on and off the stage as well as in front and behind the cameras.

No other celebrity may be able to showcase the array of toppers that Britney has donned throughout her decades-long career. Even so, who else can possibly say that they have lived a more colorful life than that of the Princess of Pop?

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