The Top 20 Essential Black Male Fashion Icons Ever: A Timeline

From Sammy Davis Jr. breaking down barriers by gracing the GQ cover in 1967, to Tyler The Creator & Luka Sabbat reimagining Black Masculinity with every outfit, here are the Top 20 Essential Black Male Fashion Icons Ever. And how they all connect.

The Culture: Joey A.X for SOULER

Culture has such a short term memory. Amplify that by 2,700 or more now. The never-ending parade of megaphones in CMYK commanding us to “click here” or “buy that” are all playing to take advantage of our lab-rat attention spans. They know that one can only hold up (or seem to semi-grasp) the last 123 posts you’ve scrolled thru. The click-bait is real. The important stuff falls valiantly to thirst traps. Don’t drink the water or the Kool-Aid.

We strongly suggest that you don’t let the in-your-face, pay-to-play media of today cloud the importance of yesteryear.

That’s why this is all about the forefathers who gave birth to that same lunacy cycle content era we live in now. Ignore all that noise of a hot second. This is far too important.

Sometimes the best place to start is the past. In my opinion, it's really the only place. Sure, in an era when pre-teens start Tik Tok trends by the day, it becomes a bit more of a concerted effort to reflect when needed.

You can’t know where you’re going without only knowing where you’ve been, but also knowing how we got here. Read the fine print. Connect dots that no one else did. The truth, much like the devil, is in the details.

The bible of Dapper Dan, a photo book shot by the incomparable fashion photographer & journalist Ari Marcopoulos for Gucci. The rare visual gems in the book alone are enough to inspire endless subcultures & new visual guidelines.

Past and future have an obvious, yet forgettable way of interacting. It all seems an easy concept to grasp but you know what they say about the “worth of ease.”

Sometimes we draw those string and thumbtacks the way the FBI agents do on all those serial killer shows linking evidence or a timeline patterned without ever recalling that at whatever place the first thumbtack was pressed in, there were probably about 50 more that should have been placed prior.

By taking all things into consideration, we’ve connected over 60 years of creating Black Fashion’s definitive “family tree” of iconic style. Not for one minute can one assume you’d have the later characters on the list without the OG’s who came first. There’s be no Theophilus London without Sammy Davis Jr, and they would be no Tyler the Creator without Kanye & young Skateboard P. Even more so, there would be zero Lenny Kravitz, Prince or Andre 3-Stacks without the god Hendrix.

jimi hendrix prince fashion style

Prince (L) in comparison to rock lord Jimi Hendrix (R) shows clearly a line of style, energy & ethos was drawn.

Here’s a really bold one, too. There would not even be “streetwear” or the “custom culture” that comes from it without Dapper Dan, and there may not even be mainstream black-owned lifestyle lines without Diddy. (You’re mad welcome, Wille Esco & Rocawear, but Diddy showed the whole world how rappers could be rack surfed moguls ahead of the curve.)

We started at the beginning because that’s where all stories should begin. There’s no better way to kick off our SOULER: “Creativity Of Color” month without taking our caps off to the first wave-makers and pioneers. We exist on your backs, and we’re all better off to know that.

“This right here is not a test.”

The time machine is fired up, ready to take us to from the Rat Pack era, to the Jiggy era, to whatever high street adventurous non-binary scene we live in now. Peace to the kings who came before us.

Sammy Davis Jr

Sammy Davis Jr. of Rat Pack fame was one stylish man. In 1967, his fashion icon status was cemented when he became the first man of color to appear on the cover of GQ. Herringbone patterns, slim British ties, penny loafers, and pomaded hair define his timeless look that allowed Black America to aspire for more. He, however, defined effortless cool and a hip brilliance that ranged from Yacht Club to Vegas for the weekend and planted a flag that has still not been removed.

Malcolm X

It almost seems contrite to put the social revolution legend on a fashion list, but he surely belongs. His dapper style, signature slim-fitting suits, and skinny ties & powerful monochromatic symmetry influenced a generation of young black men who would not be silenced any longer.

Jimi Hendrix

The posterboy for the social rebellion of the 60’s and 70’s was also a fashion icon. Layers, patterns, scarves, and shawls were feminine while his overall energy was pure alpha. He lived fearlessly, stood up for what he believed in, and inspired a generation thru not only his brilliance musically, but his style. There would be a very different Prince if Jimi didn’t exist.

Prince

It’s nearly impossible to look at a purple suit without thinking of Prince and his iconic “Purple Rain” getup. That is the power of his style. Androgynous layers, converging cultures with each veneer (from the neon dripped psychedelic, to rock, to urban to femme-boi) and absolute ownership of shit you’ve never seen before. What Hendrix began in earnest Prince made high art of.

Michael Jackson

The greatest entertainer of all time. Reaching heights that previously were reserved for Sinatra, The Beatles & Elvis, MJ broke so many ceilings for people of color. His personal style was a hyper blend of old Hollywood, avant-garde rocker 80’s futura, and Broadway musical theater wardrobe. The high-waters and white socks were originally to visually showcase his dancing, but we all know that MJ transcended any box one could ever imagine. There was the 50’s biker gang ensemble from “Bad,” the red leather jacket from “Thriller” and the military-inspired outfit he wore for his 1993 Super Bowl halftime show.

Dapper Dan

The legend that is Dapper Dan today, finally properly honored by Alessandro Michele for Gucci was and still is, a pioneer. Born Daniel Day, the Harlem couturier and original auteur of street-style elevated Black fashion in a bold, daring way. By using European luxury patterns and materials, he “reimagined” pieces for everyone from athletes, to entertainers to drug kingpins of the 80’s. DD’s style is self-described as “Knock-ups” not knockoffs- and was revolutionary when he opened his uptown spot in 1982. Dan’s bespoke garments were stamped by designer logos, they were always redesigned to include signature Dapper Dan details such as puffed sleeves or expensive fur.

RUN DMC

Technically this is “two people” (well- 3 if you count the iconic DJ Jam Master Ja7) but their iconic contribution (allllll together now, kids) to fashion has to place them on the list as a set. The 80’s and early 90’s heyday of “hip hop style” was perhaps no better embodied by the Queens rappers. Giant gold rope “dookie chains,” Dapper Dan custom luxury fits, tracksuits, bucket caps and of course, the Adidas shelltoes are all beyond quintessential. They not only made rhythmic beats and rhymes the rule, not the exception, for Top 40 music, but they influenced a generation of B-boys, Djs and urban youth in the process.

Brand Nubian

If Run DMC, Rakim & Big Daddy Kane laid the foundation for hip hop & urban style, Brand Nubian evolved it into a new narrative. The posterboys for inner city eclectic conscious rap, BN was instrumental in empowering people of color by embracing African roots. The “conscious backpack rap” wave they created also came with a trademark look - Afrocentric Fashion. Giant beaded necklaces, tribal patterns, and a convergence of several urban subculture benchmarks were the drip. BN ushered in a proud heralding of black roots, while also contributing to the indie creative spirit that gave so much to what would become “streetwear.” Hallmarks like high-low fades, razor sharp parts, huge African jewelry paired with NY sports teams Starter snapbacks and vibrant tribal patterns. You can almost look no further than “street DIY” roots beginning with BM- you know, t-shirts with messages of social justice at a revolutionary time.

Lenny Kravitz

A bit of Hendrix, Prince & Jagger with a splash of Bowie & a healthy sprinkle of Afrocentricity were the cornerstones Kravitz built his style on. Regardless of the several obvious inspirations for his style, Lenny was 100% original. The hard rock pioneer embodied badass rock n roll energy and was bold and daring in his aesthetic. Through the eras of LK, and there are eras to be sure, he’s evolved authentically from his core look and roots. We didn’t even deduct points for “that scarf”.

Ghostface Killah

90’s Gangster rap was perhaps no better embodied by one man, even as he was like a 200 person group if you even count the Wu’s extended fam and collective. From bright furs, to super baggy denim tucked into untied Clark Wallabees and Timbs, loud gold jewelry and brands like Avarex, Champion and Polo all blended in equal measure- Ghostface was the voice, and look, of the mid-90’s. Wu-Tang Clan still aint nothin to f*** with as that aesthetic returns for 2021.

Puff Daddy

Say what you will about the man we now call Diddy, but he was an absolute force at the height of his powers. He is the face of the “Jiggy Era” — a loud, ostentatious & flashy style of dress from the post-gangster 90’s to the mid 2K0s. Giant oversized urban designer wear, shiny suits, and a hyper glossy, loud leather print fearless aesthetic that legitimately became what hip hop culture looked like to the world. He was also a business genius, branding himself and his look via Sean Jean clothing, his eponymous line that opened the floodgates for what was possible for black culture. The first black man to get his whole floor section of Bloomingdales in NYC in 02 was no small feat either. He was a one man force for 20 years, and defined an era with every outfit. Bonus points for bagging peak J-Lo.

Pharrell Williams

Pharrell Williams is a one-man vanguard. The multi-instrument musician, producer, rapper, singer, and designer laid down the groundwork for the eclectic convergence culture uprising that would come in full force as a product of his vision. He was Karl Lagerfeld’s muse, and did more the merging of streetwear and luxury than perhaps anyone except Kanye. Skateboard style in urban culture began with “Skateboard P” — giving a new segment of subculture a hero. His work with Japanese streetwear legend Nigo (creating brands like Bape, Ice Cream, Human Made & BBC) led to massive collections with Adidas, CDG Play, and the creation of his media content empire iAmOther.

Andre 3000

If Hendrix and Prince rightfully make the list, then it's only fair we rank their direct descendant in the early to mid 2000s. Three stacks bucked all the “southern rapper” look trends and opted to dress himself like a walking art gallery. The rapper transitioned into acting and a host of new mediums from his early days as half of Atlanta supergroup Outkast. He blended femme, Broadway, Dandy, roaring 20’s and Motown in equal measure that opened the eyes of what a “rapper” even could present as. Goodbye 5 XL white t-shirts, Andre 3000 legit shoveled the dirt all over that shit and ushered in a better era.

Kanye West

Where to begin. As controversial as he has always been, no single human contributed to the culture shift of the 2000’s more. Ye’s “iterations” have shaped where culture goes and it’s no accident that one can draw a clean line from his albums to the look and feel of the youth. It happens every time. There’s be nothing in the CPFM/BrainDead aesthetic or today’s mysteriously pop art, cartoonish drop centric lines if it wasn’t for Ye. He’s come a long way from “College Dropout” in 2002, when he made Americana Prep a black style staple. His Adidas collaboration Yeezy turned into a whole division of the sportswear giant, and whatever he wears becomes THE look for the season from the streets to the runways. Since his emergence, his “coaching tree” reads like the Who’s Who of current thought leaders- with Virgil Abloh, Jerry Lorenzo, Don C, Heron Preston, Joe Perez and Taz Arnold all stemming from the tree of life that is ‘Ye. He has so many “edits” if his style that it almost feels like another piece, just focusing on the eras of Kanye’s style growth needs to happen. I’m guessing it will.

Theophilus London

Kanye’s aesthetic was the foundation London grew from. He evolved it into a curated blend of art gallery chic, vintage luxury hipster & high street cut x sew sensibility. He was the underground darling of all the art gallery shows and Tumblr blogs from 2007–2012, paving the way for a lot that was to be accepted. While London may not be a household name, he is in fashion circles for his fearless contribution to elevating outside-the-box looks that were previously unseen or unacceptable in mainstream urban culture. He brought in an era of non-binary accessories, hats, Daddy accessories, lapel pins, not-so-common kicks and, essentially, styles that the average spitter couldn’t pull off. London’s high cultured taste, ability to forecast trends and self-created LVRS brand caught the eye of 2010’s emerging “street luxe” style making him the underground posterboy for collabs and lookbook features. In short, London is one of the reasons why “street luxe” became a thing, quickly moving streetwear out of the $20 skate or band t-shirt into a cleaner, more experimental, and divergent understanding of it.

Lil Wayne

There is no word to really describe this straight alien. The creative genius went from NoLa 90’s 5XL hood wear to asian street-luxe, then single-handedly made skateboarding and street sports born fashion a thing, all while releasing classic mixtape after classic mixtape. He bridged a gap between what was traditional “punk” and “hiphop.” Vision has always been his strong suit, having the balls and foresight to take rap in a whole new direction with the construction of Young Money, train-spotting and giving a lane to today’s icons like Drake & Nicki Minaj, while crafting a union between lifestyles that were previously disconnected.

A$AP Rocky

Rocky A$AP — aka “Lord Pretty Flacko” has come along way from living in NYC’s homeless shelters. His drive and vision lead him to co-found the rap, fashion & creative clique A$AP MOB and the rest was history. Rocky’s signature look is the absolute lack of any rules that put young black men (especially in hip hop) in a box. From fluid, non-binary luxury to wildly oversized, bold layers and mixing streetwear with heritage high street rich kid shit, he has broken down so many barriers well outside of music. His footwear collaboration with Belgian design legend Raf Simons was a seminal moment that opened even more gates of understanding and possibility between what were traditionally opposing forces who cared little for either other.

Tyler The Creator

Without Tyler there is no “gen z” urban look. A bit SoCal skate, a bit indie streetwear, a bit full-on normcore (un)stylish dork and a bit youthful irony are the Tyler ingredients. The Creator has given a pallet to the outliers that matched the quirky, indie, disruptive sound of his group Odd Future. Tyler’s fashion work culminated in the creation of GOLF WANG, a t shirt “collection” that evolved over time into a full lifestyle line with a surreal, nostalgic childish flagship store on Fairfax in LA, the mecca of streetwear.

Virgil Abloh

Virgil emerged from Kanye’s DONDA collective roughly ten years ago and has not looked back. The Ghanian-American polymath is another one-man zeitgeist like Pharell or Kanye, but reached even more powerful heights when the high fashion world opened the high master's golden gate with LVMH naming him Director in 2018. Before he was the brand he is today, he was a DJ and designer from the midwest. His work with Kanye on crafting brands like HBA and Pyrex started the hype train that led him to disrupt the core definition of “luxury design” that blended high brow/low brow in wildly unconventional ways under the name OFF_White. Using traditionally premium materials and daring, European luxe sensibility with the urban subculture “drop” format, Off_White became the character of fashion’s new age in 2017–18. He has gone on to become a global force, taking over as Creative Director at perhaps the biggest house on earth, Louis Vuitton with one award-winning collection after another.

Luka Sabbat

From traditionally tailored to experimental streetwear, the 22-year-old multi-hyphenate is leading Black fashion’s new school. He’s been front row for about as many FW runway shows as years he’s been alive, Sabbat represents a new era, one unafraid to experiment with genre-convergence in any and every way. An early adopter of the new-skool Western aesthetic, cowboy boots are his go-to (when he’s not in outrageously dope sneakers), and oversized, gender-free everything is a recurring theme. The pairing of python boots with a Vetements denim tuxedo is arguably one of his defining moments. Sabbat’s rise as Gen Z it-boy has proven the youth aren’t here for your labels.

SOULER is a curated house + community where emerging talent + brands converge on one platform.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store