The Most Memorable (and Stylish) Headwear in Music History
A musician’s journey to becoming a cultural icon is usually filled with experimentation and creative expression. Anyone who is into fashion also knows that along the way, an artist’s personal style will play a huge part in the grander scheme of things. One thing in particular we’ve always noticed when it comes to musical tastemakers is the ongoing trend of establishing iconic headwear. It might sound a little strange, but can you even think of Frank Sinatra, Flavor Flav, or Willie Nelson without picturing their trademark dome apparel?
Take a look at some of the most memorable hats and headwear that we’ve seen throughout music history, ranging from Jimi Hendrix and Keith Richards to Run-D.M.C. and LL Cool J. If you’re still looking for a pretty ill Halloween costume, don’t be afraid to use this list as a source of inspiration.
Slash
On top of having a virtually perfect set of frizzy locks, Slash is rarely seen without his trademark black top hat. Word is, he actually got it through a “five-finger discount” back in 1985. Not to condone that type of behavior, but you’ve got to give the dude credit for consistently keeping that hat in his possession. Rocking the same one for almost 30 years is true dedication.
Michael Jackson
It’s no secret that Michael Jackson is a full-on entertainer, all the way down to his shimmering apparel. One of his main staple pieces, outside of his one bedazzled glove, was his classic fedora hat. Whether it was “Smooth Criminal” white or classic HIStory Tour black, MJ’s headgear was never anything less than immaculate. In time, it eventually became an unofficial crown for the undisputed King of Pop.
Devo
Can we all give Devo major props for rocking LEGO cones on their heads? The actual name for the "Whip It" hit makers’ hats was “energy dome,” and they were first worn during the era of their 1980 album Freedom Of Choice. We’re surprised Lady Gaga hasn’t tried to revive this trend yet.
Eazy E
The man we all know and love as Eazy E repped Compton to the fullest. When he wasn’t rocking a Raiders or Kings snapback, always black, of course, E stayed with a “Compton” cap on his cranium. Even today, images of him rocking one have a classic look to them.
Flavor Flav
As gaudy and well, tacky, as it was, Flavor Flav’s Viking helmet was truly a classic moment in hip-hop history — at least in terms of reality TV. Once Flav returned to the scene on his VH1 dating show Flavor of Love, he and his horned helmet were way too wild to ignore. We’d even sit through another season of his reality series to see him rock one again.
Bret Michaels
With the amount of bandanas that Bret Michaels wears, it actually starts to make you wonder what he’s hiding under there. Could it be one really huge, irremovable zit? Maybe it’s attached to his hair and removing it will reveal his complete baldness. Either way, the look really works for Bret, almost a little too well. We doubt people would even recognize him if he stopped wearing them.
Kid Rock
His lyrics might scream rocker or hip-hop star, but Kid Rock’s trademark fedora steez 100 percent brings out the country boy in him. You’ll typically see him donning one that’s all black, but every now and then, he’ll pull out a beige or brown version to keep things fresh. We wouldn’t expect anything less from one of the dopest entertainers to mix rap, rock, and country all on one stage.
Pharrell
The infamous Vivienne Westwood hat Pharrell wore to the 2014 Grammys made its impact less than a year ago, but the frenzy it caused almost eclipsed the music ceremony itself. Even though ‘Rell’s 10-gallon headpiece looked like it was about to swallow his head whole, Skateboy P made it work in a way that only he could. It also made for some really funny Arby’s jokes, too.
Tim McGraw
Most country stars have a cowboy hat stashed away in close proximity, but none have developed the look as their own quite like Tim McGraw. Whether he’s racking up multiple CMA awards or spending a little quality time with wife and fellow country sensation Faith Hill, McGraw is dedicated to rocking his cowboy hat consistently. Actually, the only time we can recall him not having one on is when he was acting in movies like Friday Night Lights and The Blind Side.
Run-D.M.C.
The ’80s was a defining time for hip-hop, both on a style and musical platform. Run-D.M.C. was at the helm of it all, defining the era with their chain of hit albums and unmistakable fashion staples. Outside of the adidas tracksuts and dookie chains, their classic Kangol bucket hats were definitely a big part of their entire image. These guys were innovating hip-hop and style at the same time.
Tupac
Just as iconic as the nose ring he wore in his left nostril, Tupac’s bandana game is still comparable to none. Sorry, Juelz! Some of his most iconic photos show him rocking a bandana, always tied to the front and center of his forehead. We wouldn’t have been surprised if he had launched his own line of them, if he had had the chance to reach his full potential as an artist and businessman.
Slick Rick
It’s hard to picture anyone in hip-hop more eccentric than Flavor Flav, but Slick Rick could easily come in close second. Similar to Flav’s horned helmet, Slick literally proved his rap royalty by rocking a crown to go with his ever-changing eye patch. As wild as it may seem, the look really worked for him. Unfortunately, we can’t say the same about the multiple chains, though.
Lady Gaga
At this point, it’s best to never question Lady Gaga when it comes to her fashion sense. Still, nothing will compare to the time homegirl wore a piece of meat on her head to the 2010 MTV Video Music Awards. The move was bold and a bit grotesque, but it did make a dent in pop culture history. Not only does the hat and accompanying dress have its own Wikipedia page, but it also went on display in 2011 at the Rock and Roll Hall of Fame. Talk about a fashion statement.
Jay Z
There was a point in time where Jay Z rocked a Yankee fitted so much that you would have thought he bled blue. Hov actually went all the way and launched a special apparel collection — Yankee fitted included — with the iconic baseball team to celebrate his Eminem-assisted Home & Home Tour at their stadium. Even though Jay has moved on to grown man things like Tom Ford, it’s never hard to find him rocking the iconic blue cap, sometimes even better than a Yankee can.
Lemmy Kilmister of Motorhead
Outside of his iconic muttonchops, Motorhead’s Lemmy Kilmister is pretty known for his usual black hat. The golden crisscross design on the front makes the black exterior stand out, and is usually topped off with a series of rounded buckles. It’s safe to say that you’ll never mistake this dude on the street for anybody else. Ever.
Keith Richards
When you’re a member of the most iconic rock group of all time, you’re pretty much allowed to wear anything you want. We’re sure that’s in a rulebook somewhere. Thankfully, the Rolling Stones’ guitarist Keith Richards chose a consistently dope set of bandanas. Sometimes they were red, and other times they were blue, but one thing he made sure of was that they always complemented his cool factor. Job well done for sure.
Jimi Hendrix
The funk and soul icon known as Jimi Hendrix was all about eclectic prints and patterns to match his psychedelic persona. In order to keep his free flowing ‘fro intact, Hendrix would usually tie it down with a colorful bandana. Even in 2014, nobody comes close to matching his trippy style. Andre 3000 [LINK: http://green-label.com/sound/jimi-hendrix-biopic-all-is-by-my-side-official-trailer/] made a nice attempt, though.
LL Cool J
While Run-D.M.C. was busy changing the game with the black Kangols, LL Cool J was on his own lucrative path to hip-hop stardom, rocking a red version of the popular bucket hat. The majority of the promo stills from LL in the ’80s show him wearing the classic red Kangol with pride, even rocking it on the back cover of his 1985 Radio album. No wonder why all the ladies loved him.
Willie Nelson
The well-known red bandana that Willie Nelson wears to hold down his wild mane of hair — which he still has a full head of at the tender age of 81 — is almost as iconic as the country hits he’s been putting out for the better part of 60 years. Hopefully he’s still rocking one for another 80 years of great music and powerful moments of activism.
Frank Sinatra
We couldn’t talk about famous hats in music without mentioning Frank Sinatra. The man was always stylish with everything he laid his hands on, and thankfully one of those things was a fedora hat. Artists like ZZ Ward wear fedoras specifically to pay homage to Ol’ Blue Eyes, and he’s definitely worth the tribute in every sense of the word.
A musician’s journey to becoming a cultural icon is usually filled with experimentation and creative expression. Anyone who is into fashion also knows that along the way, an artist’s personal style will play a huge part in the grander scheme of things. One thing in particular we’ve always noticed when it comes to musical tastemakers is the ongoing trend of establishing iconic headwear. It might sound a little strange, but can you even think of Frank Sinatra, Flavor Flav, or Willie Nelson without picturing their trademark dome apparel?
Take a look at some of the most memorable hats and headwear that we’ve seen throughout music history, ranging from Jimi Hendrix and Keith Richards to Run-D.M.C. and LL Cool J. If you’re still looking for a pretty ill Halloween costume, don’t be afraid to use this list as a source of inspiration.