The Freshest Fashion Moments in Hip Hop History
Like all transformative cultural movements, hip hop has had its fair share of classic moments. From those first park jams to the blockbuster videos, from the magazine covers to the awards shows, to the tragic deaths of some of our best and brightest stars—these are the moments that define the culture, bringing together like-minded individuals for a common cause: Life, liberty, and the pursuit of freshness.
With the Mass Appeal / CNN Films production Fresh Dressed debuting on silver screens and on-demand today, we've been thinking a lot about fashion and hip hop (hence our #FreshDressedWeek). There are so many moments worth highlighting, moments during which freshness was a defining attribute. And so without further ado, we present the 50 freshest fashion moments in hip hop history.
50. Macklemore "Thrift Shop" Video (2012)
We know what you're thinking: "What? What? What? What?" Despite all the fuckery surrounding Macklemore’s ascension to the top of the rap industry, (we all know "Thrift Shop" shouldn't have won Best Rap Song at the GRAMMYs), you can't deny this track's reach and influence. When the single hit number one back in 2012, it became the first independent single to top the Billboard pop charts in nearly 20 years. And at nearly a quarter of a billion views, the music video is out here even if you want to pretend it doesn't exist. The rapper you love to hate had everybody and his uncle taking it Grandpa style.
A departure from the designer name-dropping found on so many hip hop tracks, "Thrift Shop" finds Macklemore and Ryan Lewis letting the world know that you can get fly with only $20 in your pocket. Say what you want about white privilege, but Macklemore's actually echoing some of the insights expressed in our Fashion Gems series by the likes of Dapper Dan, Dame Dash, and Wu-Tang's Cappadonna. At its core, hip hop is about self-expression—not out-spending the competition. And while it ain't trickin' if you got it, we're definitely not mad at those who can stay fresh for less. While it's debatable whether Macklemore actually increased the amount of people out here thrifting, the "looking for a come up" ethos of "Thrift Shop" is hip hop. (Though you definitely should wash second-hand threads first.) We can't personally cosign the heinous fur coat Macklemore rocks in the clip, but it's working for him.
49. Doug E. Fresh and The Get Fresh Crew "All the Way to Heaven" Video (1986)
Taking hip hop’s sneaker wars to a whole other level, Doug E. Fresh and The Get Fresh Crew rep hard for the Bally brand in this single off their debut album Oh My God, the first release following MC Ricky D’s split from the camp that would culminate in his Def Jam debut The Great Adventures of Slick Rick. Still rockin’ with New Jersey indie Danya/Reality/Fantasy Records, Doug and his ride-or-die comrades The Cut Mix Mystro D.J. Chill Will and The Cut Professor Barry Bee stunt all over this state-of-the-art old-school video featuring a classic hip hop jam poster that comes to life opening up into a Technicolor fantasy world in which two pair of sneakers—unlaced adidas Superstars and some old-school Bally high-tops—have a Wild West showdown. The Bally’s aglets spit hot fire, gunning down the adidas in the street while Doug raps “People want us to break up but we cannot.” (Why? Cause they’re on a mission!) Incidentally, this record was released the same year as Run-D.M.C.’s “My Adidas.” Shots fired?
48. Theophilus London "Humdrum Town" Video (2010)
Before he was rubbing shoulders with Kanye West and Karl Lagerfeld, Theophilus London was the young fly guy from Brooklyn with an outside-the-box aesthetic. Today, folks might misappropriate his look as a Euro-inspired-hispter steez, but Theophilus was rocking this look before it was cool. (Wait, that's actually some really hipster shit to say.) In 2009, young Theo's This Charming Mixtape was being shared amongst iTunes aficionados from dive-y downtown bars in NYC to dorm rooms at Syracuse University (peep the hat). So when the video for "Humdrum Town" finally premiered on MTV in 2010, the world took notice and tuned into to what Mr. London had to say. While heads remain divided on his music, there's no denying Theophilus London established himself as a tastemaker in fashion from the get-go. Remember kids, even when your album doesn't sell, you can still cash a check doing car commercials.
R.I.P to Winnie's (the bar where the karaoke scene was filmed).
47. 2 Chainz "I'm Different" Video (2013)
Those who have been paying attention know that the artist formerly known as Tity Boi has always been about his style. Since that T.R.U. REALigion mixtape he's been letting us know that his belt-buckle game is next level. But the moment everybody realized 2 Chainz was a bonafide style icon came after watching his video for “I’m Different.” Sporting head to toe Jeremy Scott for adidas, right down to the J Scott “Gorilla” sneakers, Chainz proved visually what the song was saying lyrically. Who else could pull off a look this outlandish? Add the fact that he was cruising down the highway in the back of a boat throughout, game over.
46. TLC "What About Your Friends" Video (1992)
With T-Boz as the short-haired crooner, Chilli as the long-haired charmer, and Left Eye as the rappin’ wild child, the ATL R&B-pop act made waves with their style as much as their sound. On the Lionel C. Martin–directed video for the third single from their smash debut Ooooh… On The TLC Tip, the trio broke the mold with eye-poppin colors and baggy spray-painted pieces, plus Left-Eyes oversized hats and signature condom accessories. Though their looks may have been too extreme to imitate in real life, TLC's unisex swag set trends like a hood couture collection straight from the bubbling black music hotbed of Atlanta.
45. Migos “Versace” Video (2013)
Migos were certainly not the first to rock Versace in Hip Hop—most of the greats, from Tupac to Jay-Z —had been there and done that by the time they came along. But there is no denying that these Atlanta trap-rappers revitalized the brand with their 2013 hit song, “Versace,” glorifying the Medusa-head and landing it on a new generation of hip hop fashion lovers’ backs everywhere (whether real or bootleg). Between their illustrious video, including a brief cameo of Donatella Versace, and Drake hopping on their remix, Migos further solidified Versace’s enduring place in rap culture.
44. Kanye West Rocks H&M Versace Jacket at Victoria’s Secret Show (2011)
On November 29, 2011 Jay and Ye made history again when they performed The Throne's smash single "N***s in Paris" on the runway before the Victoria's Secret spring collection. While Jay opted for the Givenchy jacket, Jesus piece and all-black-everything uniform, Kanye broke the mold. Instead of donning an expensive designer piece for his performance, Kanye West chose to rock a Versace for H&M bomber jacket, leather jeans, and the yet-to-be released Nike Air Yeezy 2s. Compared to Kanye's regular wardrobe, the bomber came in at just $129, a price-point accessible for nearly everyone. The frenzy that ensued after Yeezy rocked the jacket, made that jacket the most sought-after piece from the Versace x H&M capsule.
43. Juelz Santana's All-American Flag Outfit in "Dipset Anthem" Video (2003)
We all know Killa Cam straight slayed the fashion game when he was decked out in the all pink fits. But don't sleep on Juelz Santana's style game. His bandana-folding technique alone deserves honorable mention, and the all-American outfit he rocked in the “Dipset Anthem” video took his swag to new heights. Santana's patriotic getup was so dope that it even became the inspiration for a Supreme sweatsuit. Call Juelz the red-white-and-blue Robin to the Cam’s pink-and-fluffy Batman.
42. A$AP Rocky “Goldie” Video (2012)
A$AP Rocky has been about his fashion since day one. Flashback to the music video for "Purple Swag," which introduced Rocky to the hip hop world, and note the Harlem rapper casually name checking Rick Owens and Raf Simmons while dressed in Black Scale and Jeremy Scott adidas. As of this writing Rocky remains at the forefront of merging streetwear and high fashion, and perhaps no moment is more indicative of that fact than the music video for his Hit Boy-produced track "Goldie," the lead single off Long.Live.A$AP. In the video you can catch Rocky and A$AP Yams (RIP) mobbing out in Paris, riding down the Champs-Elyées in a pimped-out ride, and pouring out bottles of Cristal. Smoking, drinking, and partying with naked models, all with the Eiffel Tower in the background. Rocky linked with Alexander Wang for the Paris shoot, which finds Flacko rocking full-length minks, baby foxes, Ksubi boots, gold Margiela sneakers, and jawns from the likes of Acne, Rick Owens, and Alexander Wang. Safe to say that the fashion game in this clip is serious. And who can forget how Rocky popularized that SSUR Comme Des Fuck Down beanie that everyone and their mother was rocking for a hot minute?
41. Missy Elliott and Ludacris "Gossip Folks" Video (2002)
So much freshness was going on in the music video for this Timbaland-produced hit single, that it's hard to know where to begin. Missy sports a range of classic B-Girl fits, from her burgundy and pink-accented Adidas tracksuit with the matching pink-fur Kangol to the blue tracksuit and the yellow visor. Meanwhile Luda pimps out the alligator suit while rocking a bandana under his top hat. The low-key highlight is young Alyson Stoner (later casted in Cheaper By The Dozen), who pops-and-locks and Crip-walks her way to teen stardom while backing Missy up. Thirteen years later, shorty's all grown up, and still dancing to this song.
40. Nelly ft. Paul Wall, Ali, and Gipp “Grillz” Video (2005)
“Grillz” opens up with the prophetic statement “We ‘boutta start an epidemic with this one,” and they could not have been more right. With the assistance of Southern rap stars Paul Wall, Ali, and Gipp, Nelly’s earworm hit helped push diamond-studded teeth coverings, aka ‘grills,’ into the mainstream lexicon. Previously only popular in southern U.S. cities like Houston and Atlanta, nowadays you can see people from all over the world rocking grills.
39. Mary J. Blige and Grand Puba on 'Yo MTV Raps' (1993)
While making an appearance on Yo! MTV Raps to support Mary J. Blige for the title track of her debut album What's The 411?, Grand Puba basically murdered the Polo game with his Alpine Rugby. The Fila visor was a nice addition to his outfit, not mention the fact that he performs alongside Mary J. Blige, who's draped out in Cross Colours from head to toe as she kicks rhymes through most of the song before belting out some sick runs as the track fades. All hail the queen.
38. Jay Z and Beyonce "‘03 Bonnie & Clyde" Video (2002)
If this isn’t relationship goals, I don’t know what is. This video was the beginning of the biggest power couple in the game, and nothing is more of a flex than matching footwear that is straight fire. Jay and Bey were at the top of their game, and they stepped up the steez big time for Bonnie & Clyde.
37. Fabolous “Can’t Deny It” Video (2001)
There was a certain moment in the 2000’s when throwback jerseys (particularly Hardwood Classics) were immensely sought after. Thanks to overwhelming demand and allure in hip hop culture, some of the prices reached stratospheric levels. If you had a Washington Bullets jersey of any kind, heads would be turning left and right. The man who single-handedly owned this fashion statement was Brooklyn’s own Fabolous. He can be found sporting throwbacks in many of his classic videos, but the clips that started it all was the Nate Dogg-assisted "Can't Deny It." Reppin' every sport from baseball to football, Fabo had every young’n in the neighborhood trying to holla back at those vintage jerseys.
36. Outkast "Bombs Over Baghdad” Video (2000)
When it comes to hip hop fashion, the zaniest of them all has to be Outkast. Each and every music video from the ATLiens broked new sartorial ground—blending Atlanta street looks with Andre's funkadelic-futuristic flair—and never more than with the visuals for their hit crossover single, "B.O.B. (Bombs Over Baghdad)." Not only does 3-stacks rock a funky leopard fedora, but he complements his shirtless look with flashy, high-waisted golf pants. Generally much more kicked back than Andre, Big Boi finds himself switching from denim button-downs to football jerseys, as his hairstyle morphs from cornrows to free-flowing locks. Besides the fresh attire and hairdos, the color-correction in this video is insane, yet very fitting for such an unconventional record. Not only did Outkast embody style, they took it to new plateaus.
35. Busta Rhymes ft. P. Diddy and Pharrell "Pass The Courvoisier" Video (2001)
Endless style points must be awarded to Busta Rhymes, one of the biggest emcees in the game to really take risks when it came to fashion. His quirky personal style made all those dreadlocks-era Busta videos captivating to watch. Look no further than “Pass the Courvoisier,” wherein he holds his own alongside style icons in P. Diddy and Pharrell Williams. Pharrell kills it with trucker-cap chic while Diddy's white du-rag tux ensemble is priceless. But Busta's looks keep raising the bar from red silk to animal fur and denim jacket. This was one hell of a video that dripped swagu from start to finish.
It's important to note that three years later, Diddy won the CFDA Menswear Designer of the Year award. Though it may have surprised some to see the founder of what began as a streetwear brand winning the coveted award, this moment was years in the making. Diddy had been nominated four times previously, and the Sean John collection had been going strong for years. When he became the first black man to win this award, Diddy not only represented himself and his company, but the hip hop culture as a whole. We have to give props to Pharrell as well for taking home the 2015 CFDA Fashion Icon Award.
34. Ghostface Killah "Cherchez La Ghost" Video (2000)
Ghostdeini is one of the most notorious cozy boys of all time. From slippers to robes—always rocked with disgusting amounts of jewlery—GFK wrote the book on bedroom swag. Matter of fact, Tony Starks sonned anybody trying to test his leisurely style in the video for “Cherchez La Ghost.” When Ghostface wasn't straight draped in the plushest robes, he rocked the Gucci tracksuit or whipped out the green fur on them. All hail the Wallabee Champ cozy boy pioneer. He's got the championship belt to prove it.
33. De La Soul "Me Myself and I" Video (1989)
Let's be honest, De La Soul are not first guys who come to mind when you envision the concept of "fresh." However, much like the other members of the Native Tongues collective, De La wholly embraced love of self, which manifested into a unique sense of individual style. The group's funky-dread haircuts, Africa medallions, and urban-bohemian swag reached its zenith in the music video for their breakout hit, "Me, Myself, and I." Juxtaposing Posdnuos, Trugoy, and Maseo's respective steez against the reigning stereotypes of the era—ghetto blasters, dookie rope chains, and cookie-cutter B-boy posturing—De La and visionary founder Prince Paul created a sophisticated dialogue about what it really means to be cool. While some chased trends, this crew found comfort in their own skin. How fresh is that?
32. The Pack "Vans" Video (2007)
Say what you will about The Based God and his Internet antics (we just say "Thank You") nobody can deny the impact of his group's sneaker anthem, "Vans." The viral success of this video on Myspace would lead the Bay Area rap commander Too $hort to sign this group to Jive—continuing the Bay's legacy with the label (see Souls Of Mischief's 93 'til Infinity). As The Pack's record grew in popularity, $hort hopped on the remix alongside fellow Yay Area legend E-40. In the late 2000s it seemed like every other kid, whether they ever or not touched a skateboard in their life, was rocking those signature slip-on sneakers, most likely drawing custom designs on them in a classic hip hop fashion.
31. Dem Franchize Boyz “White Tee” Video (2004)
This ATL rap quartet—responsible for club bangers like "Lean Wit It, Rock Wit It," "I Think They Like Me," and "Ridin' Rims"—is not given much credit as style trendsetters. But their 2004 cut "White Tee" was a hood fashion anthem by any measure. While it might not have reached the top of the Billboard charts—peaking at a respectable 25—it did set off every Champs, Foot Locker, and neighborhood corner store in America as everyone and their cousin lined up to cop their oversized "tall tees." While some may be afraid to admit ever sporting these shirts, there was a time where this was undoubtedly the freshest low-budget look in hip hop fashion.
30. Odd Future Brings Supreme Mainstream on Jimmy Fallon (2011)
While Supreme was already an important brand in skate culture-leaning segments of hip hop prior to Odd Future, the group definitely boosted the iconic box logo to new heights during their rise to prominence. The unforgettable moment that introduced the brand to mainstream audiences came during OFWGKTA's late-night television debut The Jimmy Fallon Show. The iconic performance of "Sandwiches" began with Tyler, the Creator wearing a white Supreme hoodie, and ended with him placing his five-panel camp cap on Jimmy Fallon's head while piggy-backing him. Odd Future definitely defined how a generation of kids dressed (for better or worse), and that influence lives on today even though the group is no more. In case you missed it, make sure to take a look back at our brief history of Odd Future.
29. Kanye West Debuts adidas Yeezy Collection at Grammys With Velour Sweatsuit and Kim K (2015)After a six-year hiatus, Kanye West returned to the Grammy Award stage with a performance of his track "Only One," an ode to his daughter North West. Wearing a burgundy velour sweatsuit, Yeezy appeared as a lone figure on the circular podium, circling a spotlight while rocking his never-before-seen Yeezy 750 Boost sneakers. Kanye’s live performances are always visually striking and feature iconic outfits, but what made this one especially notable was this was a 100% Kanye-designed outfit. Kanye's latest foray into the fashion world was met with mostly positive reviews, a degree of acceptance that Kanye has been working towards for years now. In his Paper cover essay from earlier this year, West revealed that "right now, over 70 percent of my focus is on apparel." That fact has some worried about the fate of his upcoming studio album SWISH, but when has Yeezus ever let us down?
28. The Beastie Boys "No Sleep Till Brooklyn" Video (1986)
The Beastie Boys’ “No Sleep Til Brooklyn” signifies the birth of the frat hipster look that is still present to this day. From the cuffed skinny jeans to the snapback caps, all the way to the Wayfarer sunglasses. The Beasties' zero-fucks-given attitude while rocking their individual yet unified looks set the tone for how kids who didn’t come from the inner city could approach hip hop fashion in an unselfconscious way. This is the crucial missing ingredient that so many fuckboys fail to grasp.
27. N.W.A "Express Yourself" 12" Single Cover (1988)
The look depicted on this cover—all-black outfits comprised of coaches jackets, black crew necks, black skinny jeans, Los Angeles Raiders caps, and fat gold dookie chains—would forever change West Coast fashion, along with hip hop fashion in general. The dispassionate demeanor shown on the cover made the look even more relevant, because these "gangsta rappers" truly didn't give a fuck, an "attitude" that relates directly to the spirit of hip hop. The N.W.A look was part militant, part dopeboy, and extremely affordable—three things that scared the hell out of conservative America.
26. B.G. ft. Hot Boys and Big Tymers "Bling Bling" Video (1999)
You're looking at the genesis of Cash Money's gaudiness. In retrospect, it's almost shocking how modest the Cash Money Records crew's jewelry is compared to the excesses that lay ahead. But there's no denying that the proliferation of the phrase and concept of "bling" is a direct result of this song and video. (Whether or not that's a good thing is up for debate, but it is what it is.) "Bling Bling" paved the way for future visual exposés on stuntin' from Cash Money members like Big Tymers' "Still Fly" and Lil Wayne's "Shine." (We'd like to give a special shout out to the big homie Mannie...Fresh.) While Cash Money is currently caught up in a contractural clusterfuck, we can't help but smile at the sight of a baby-face Wayne and Baby in matching white tees and CMR chains blingin' with the rest of the squad. This song had such pop-cultural impact that we still have to grimace every time an older relative uses this phrase.
25. Nelly "Air Force Ones" Video (2002)
If you didn't already have a fresh pair of AF1s to rock, when this song dropped you went out and copped some. Nelly's not someone we'd normally consider a fashion icon—because a band-aid on your face and an upside-down-backwards visor is not cosignable—but he sure as hell knew how to capture the essence of a style trend on wax (see "Grillz"). The Air Force One hype was so crazy that we knew dudes who earned a sustainable income solely off airbrushing these kicks. Out of all the styles the St. Lunatics mention, we're going to have to agree with Nelly that the all-white Forces with the gum bottom are the freshest. No idea what's up with the constant "big boy" sample in the background though...
24. RZA ft. Method Man and Cappadonna “Wu Wear The Garment Renaissance” Video (1996)
Fresh off of releasing pivotal projects like Raekwon's Only Built 4 Cuban Linx and Ghostface Killah's Ironman, Wu-Tang Clan mastermind RZA was riding a wave of worldwide critical acclaim when they decided to capitalize off their name and likeness in the form of Wu-Wear. And what better way to break your new clothing line than through a song that doesn't suck? Not only did this cut off the High School High Soundtrack spread awareness of the Wu's clothing brand, but it also led to them opening a brick and mortar storefront for Wu-Wear. And the looks in this video are striclty fresh to death.
23. Kriss Kross Wear Backwards Clothing in “Jump” Video (1992)
Before Kriss Kross, the idea of rocking your clothes backwards as a fashion statement was unfathomable. But on the Jermaine Dupri–produced crossover hit "Jump" the teen rappers laid down the law: "everything is to the back, with a little slack / 'cause inside out is wiggity wiggity wiggity wack." The ATL duo's look was so iconic that Michael Jackson took Daddy Mac and Mac Daddy on his Dangerous World Tour. The young rappers even had Arsenio Hall questioning them about how they went to the bathroom.
22. LL Cool J Rocks The Gap...With a FUBU Hat (1999)
In 1999, LL Cool J finessed some of the greatest free publicity any brand has ever received. As Queens-based designer Daymond John’s FUBU was just getting started, Cool J became an early supporter. When The Gap approached him with a commercial deal in which he would freestyle for the camera while wearing some basic Easy Fit Jeans, he decided to rock a FUBU hat to the shoot. On top of that, he even worked in FUBU’s slogan “For Us By Us—on the low” into his lyrics. Completely unaware of what was going on, The Gap's gate-keepers did not catch the subliminal shout out and funded the commercial in full, pushing FUBU into homes nationwide. How fresh is that?
21. UGK ft. Outkast "Int'l Players Anthem (I Choose You)" (2007)
You can't do a list about Freshest Dressed Moments in Hip-Hop without Pimp C. The late great Chad Lamont Butler's swag shines through in the stuntastic music video for UGK's fifth studio album Underground Kingz, which focuses on the very-much fictional wedding of internationally known style trendsetter and ladies' man Andre 3000. Dre rocks a red Scottish kilt to the alter, as he's mocked by Bun B of UGK and accompanied by Big Boi of OutKast, and the video also boasts cameos fromThree Six Mafia (who produced the track), T-Pain, Chamillionaire, David Banner, Big Gipp, and Fonzworth Bentley. But all of that becomes irrelevant as soon as Pimp C shows up during the reception in a white fut coat and matching hat. "Every time we hit the parking lot we turn heads," he raps on the song—one of the last he would release before his untimely passing. Still the man went out just like he lived—fresh.
20. Tupac Walks the Runway for Versace (1996)
There’s no denying the universal influence that Tupac carried with both his music and his swagger. All those archival photos don't lie—whether he was wearing designer threads or just tatts and a bandanna, ‘Pac always had that flavor. But when he walked the runway for a 1996 Versace fashion show with his girlfriend Kidada Jones, he proved that his influence radiated beyond the streets. While all these other rappers were name-dropping Versace, Makaveli was in Milan strutting his stuff for the outstanding luxury label.
19. Kanye West Performs “Runaway” With Pusha T at the MTV VMAs (2010)
"Oh, you was watching? Who the fuck wasn't?" Pusha T not-so-humbly inquires on "Christian Dior Denim Flow." While King Push's salmon-colored suit was definitely a sartorial highlight, all eyes were on Kanye West when he performed "Runaway" for the first time accompanied by his MPC drum machine and a troupe of ballerinas at the 2010 MTV Video Music Awards. The opening shot from the ceiling is so damn cinematic it feels more like a Stanley Kubrick film than live performance footage. Donning an all-red suit with a black T-shirt, his neck adorned with gold chains, Kanye resembles a malevolent demigod as he delicately strikes the MPC. As a fan, it was hard not to pore over the lyrics of "Runaway" and rewatch this clip dozens of times in the month that followed. If Kanye ever decides to call it quits, remember this moment as the hallmark of his duality as fashion icon and musical savant.
P.S. That opening shot though!
18. Jay Z 'Reasonable Doubt' Album Cover (1996)
HOV's debut album turned 19 as of yesterday, but the cover art still looks fresh as hell. The '90s were dominated by various forms of gangsta rap, but seldom did we see rappers portraying the original gangster image straight out of a Scorsese flick, that is, until Jay Z came around with Reasonable Doubt. From the tailored suit to the pinky ring and cigar, Jay's ensemble on his debut album, photographed by Jonathan Mannion, birthed the subgenre of mafioso rap, soon to be adapted by The Firm and many others. Right from jump, the Jigga man looked like he was all about those dead presidents.
17. Will Smith Rocks Cross Colours on 'The Fresh Prince of Bel-Air' Christmas Special (1990)
Leading the charge as hip hop invaded the living rooms of middle America, Will Smith—aka the first rapper to win a Grammy—played a huge role in the 90s streetwear boom. As detailed in the film Fresh Dressed, the defining moment of his influence came during the 1990 Fresh Prince of Bel-air Christmas special when he took to set rocking up-and-coming designer Carl Jones’ streetwear brand, Cross Colours. It was a moment that signaled to the fashion industry that maybe America was ready for streetwear to hit the mainstream.
16. Aaliyah's Tommy Hilfiger Ad Campaign (1997)
The late great Aaliyah is one of the most iconic human beings in hip hop culture. Though she never rapped herself, this R&B ingenue sang alongside hip hop greats from Nas to Slick Rick to DMX and flowed over some of Timbaland's most futuristic beats. And her style was always unquestionably hip hop. When “Baby Girl” starred in a Tommy Hilfiger campaign at the height of the brand’s heyday, she stole the show from the likes of Mark Ronson, Kate Moss, and Simon Rex. The legendary shoot resulted in iconic shots of the R&B princess rocking red-white-and-blue with a peek-a-boo boxer waistband that were all worthy of hanging on your bedroom wall. Has the tomboy steez ever looked better?
15. Afrika Bambaataa & Soul Sonic Force "Planet Rock" Video (1982)
To modern eyes, Afrika Bambaataa & Soul Sonic Force might resemble a cross between the Village People and Power Rangers villains, but we still gotta give a nod to hip hop's forefathers. There's no better example of an iconic crew with an eclectic and unique sense of style. Though clearly influenced by Parliament-Funkadelic they give it their own futuristic Zulu Nation spin. While we wouldn't personally rock any of Bambaataa & Soul Sonic Force's looks today, there are plenty of examples of classic freshness in this music video. We gotta give a special shout-out to whoever edited this video, intercut with true B-Boy looks and rec-center-jam-appropriate apparel. That build at 2:25 still gets us hype all these years later.
14. Public Enemy “Fight the Power” Video (1989)
With a big personality and an even bigger clock around his neck, Flava Flav brought the hype to Public Enemy’s 1989 anthem “Fight The Power.” Flav flipped the rules of fashion on their heads and took it back to basics: Individuality, style, and self-expression. Though some might scoff at his outrageous look, Flav embodied the youthful, rebellious attitude of so many hip hop fans at the time and still today.
13. Lil Kim ft. Lil Cease "Crush On You" Video (1997)
“You know what Kim, we need to do something crazy and different," explains former Lil' Kim hairstylist Eugene Davis in regards to Queen Bee's hair for her iconic "Crush On You" video. Kimmy Blanco was anything but blanco in this video, pulling off multiple fur coats and matching wigs in just about every hue of the rainbow. (And please don't sleep on Lil' Cease in his yellow outfit and pinstriped suit, or the celebrity cameos from Uncle Luke and Aaliyah.) But at the end of the day, this one's all about Queen Bee, who rocks each wig—with matching shades—in a completely different hairstyle, adding an extra touch of freshness to each look. Inspired by Brooklyn bashment style, Kim took her multicolored-wig game to the ultimate spotlight when she wore the metallic purple joint along with her matching seashell pasty on her left breast at the 1999 VMA's, inducing 55-year-old Diana Ross to play with her titty on national TV, inspiring future homages from Miley Cyrus to Rihanna.
12. Big Daddy Kane “Ain't No Half Steppin” Video (1988)
Big Daddy Kane was Brooklyn's finest before Big and Jay stepped on the scene. Known to be a smooth operator, this classic '88 video proves just how buttery the King Asiatic's style really was. A tailored suit, a few gold ropes, a four-finger ring, and a fresh high-top fade was all the Juice Crew representer needed to establish himself as a fashion icon. And it didn't hurt that he had some of the nicest rhymes on wax during the era. Go to the 1:08 mark and check the homie's face as he realizes he's no match for Kane ("pick a B.C. date cause you're history"). That's the same look the haters had when they saw BDK step into the spot. However, the highlight of this video has to be Kane cold chillin' in his corner of the boxing ring with a bottle of bubbly on ice.
11. Suge Knight, Snoop, and Tupac Cover 'The New York Times' Magazine (1996)
When this New York Times magazine cover story dropped in January 1996, nobody saw it coming. Hip hop was dominating the radio, and the bicoastal war was heating up, but mainstream media outlets were not fuckin' with hip hop on any major level. Enter the enterprising Lynn Hirschberg, who got unprecedented access to the inner workings of Death Row at a time when most rap journalists were scared to speak Suge Knight's name in public. The article, "Does A Sugar Bear Bite?" stands as a must-read artifact of a unforgettable moment in hip hop. The cover image, showing Suge in Piru-red suit, Snoop dapper dark suit, and Pac in a Moschino belt, baggy jeans, leather vest, and brown hardbottoms counting money. The trio personified the apogee gangsta fresh circa 1996, just the shots started ringing out.
10. Nas ft. Puff Daddy "Hate Me Now" Video (1999)
Forget, for a moment, the whole crucifixion controversy that surrounds this epic Hype Williams video. Forget Puffy's angry demands to re-edit the video, punctuated with blunt-force champagne bottle. Let's get to the fresness. Let's get to Puffy and Nas, two rap superstars, draped in fur—Esco with the fur hat, mind you—popping bottles surrounded by hot girls in the club. Don't hate them, hate the money they see, clothes that they buy. Like Nas says, "Hate my dress code / Gucci this, Fendi that / What you expect, ho?" Go ahead. Do it now! Just remember money is power, and they've got millions of thugs on salary.
9. Pharrell and Nigo at the MTV VMAs (2006)
One of the smartest career moves Pharrell Williams made early on was joining forces with Japanese streetwear pioneer Nigo (the visionary founder of A Bathing Ape) to form Billionaire Boys Club (BBC). One of the first and most memorable moments of exposure for the brand came at the 2006 MTV Video Music Awards, when Pharrell and Nigo sported their brand all over the red carpet. Later that night, Pharrell took to the big stage draped in BBC to perform "Money Maker" alongside Ludacris and The Pussycat Dolls. It wouldn't be long before kids were saving up their allowance money to cop some Pharrell-curated threads, in hopes of either looking fresh, making a quick flip, or becoming a young entrepreneur like Skateboard P himself.
8. Cam’ron All-Pink Fur Outfit (2002)
Those who grow up in Harlem learn about stuntin' at an early age. So you already know Cam’Ron had to stunt on everybody when he showed up at the 2002 Mercedes Benz Fashion Week. What better way to make a splash than with the all-pink mink coat, pink mink hat, and pink flip phone? Later, in the split video for "Get 'Em Girls" and "Killa Cam" he rolled out in a matching pink Range Rover (which he later put up for sale on Ebay.) Still this moment would later be immortalized on pillows, shower curtains, home decor accessories and a million Internet memes. Kanye may have pioneered the pink Polo but it's Killa Cam who owns the color in hip hop.
7. Salt-N-Pepa “Push It” Video (1997)
With their shiny spandex unitards, custom leather jackets, red boots and fat gold ropes, Salt-N-Pepa's unified look set the stage for how ladies could be stylish and sexy at the same time, all with a hip hop flare. These rap pioneers blazed trail for females in a male-dominated industry, and to this day, you still see women wearing shiny spandex in the same vein as Salt-N-Pepa. And we can't help but think that they were inspired by this Peter Lauer and Anthony Forma–directed video.
6. The Notorious B.I.G. ft. Puff Daddy and Ma$e "Mo Money Mo Problems" Video (1997)
First off, R.I.P. Notorious B.I.G., one of the most influential hip hop icons of all time. Nobody could replicate the man's flow—shit, Guerilla Black caught flack for even sounding like Biggie—and his style remains unparalleled. From "Juicy" to "Hypnotize," B.I.G. rocked a wide array of styles during his time on Earth. From Phat Farm sweats and Timbs to custom-tailored suits and Versace shades, Big Poppa's swag was immaculate at every price point. Many tried to replicate but few could duplicate. Combined with the Harlem flash of CEO Sean Combs and Murder Mase, the Bad Boy crew was arguably the freshest in the rap game.
Their over-the-top music video for "Mo Money Mo Problems" stands as a testament to that legacy—even though it's since become emblematic of Puff Daddy's shiny suits. A few folks we know had even forgotten that this track appears on Life After Death, not No Way out. Regardless, there's no denying Diddy dominates this video. Shiny suits, all-white Hamptons-beach-party ensembles, parachute outfits with matching goggles—all hallmarks of Puffy's inimitable style. Super-stylist June Ambrose (who met Puff as an Uptown Records intern) gets the credit (or the blame) for talking the Bad Boy boss into wearing the metallic shiny suits (which were inspired by her childhood memories of Carnival on the Caribbean island of Antigua). It's important to note the Tiger Woods-inspired opening, a testament to how popular golf had become following his success (who would have thought at the time that Puffy would end up more respected than Tiger). Props go to Hype Williams for being able to corral all the extravagance into a cohesive visual.
5. Slick Rick Poses for Janette Beckman ('90s)
How many rappers have rocked fat gold chains and extravagantly shiny accessories all over their wrists, knuckles, and mouth? Countless. How many have done it better than Slick Rick? Zero. "Scoopin all the girlies' numbers with my truck jewelry," Rick raps on "Indian Girl (An Adult Story)" off his classic debut album, The Great Adventures of Slick Rick, "cause I'm a fly brown bother, and ya can't school me." True, that. Rick wears a crown in this iconic image from the legendary Janette Beckman photo shoot with good reason. Whether it's rhyming or flossing, he is, quite simply, The Ruler.
4. Wu Tang Clan "Can It Be All So Simple" Video (1994)
With his extravagant jewelry and colored Wallabees, Ghostface gets the most credit as Wu-Tang's fashion trendsetter, but Raekwon has always been a low-key style icon. The Chef rocking this Polo piece in a legendary early Wu video sealed the fate of this infamous jacket, to the point where it's now identified as the Raekwon Snow Beach jacket. According to Dallas Penn, this jacket was already hard to get around the time that video came out. Now it's one of the many grails of Polo pieces for 'Lo collectors.
3. The Notorious B.I.G. and the Coogi Sweater (1994)
There may be no better argument for Biggie’s unparalleled cultural impact than his ability to reclaim the multicolored Coogi sweater from Bill Cosby, transforming corny bougie-dad attire into classic hood fresh with his much-debated lyric “black and ugly as ever / however I stay Coogi down to the socks. (Who knew back then that Cos was peelin’ more skins that Idaho potatoes too?) This Dana Lixenberg photograph of Big Poppa counting Benjamins—an outtake from a 1996 VIBE magazine shoot that appeared in the 2003 Biggie biography Unbelievable—now graces countless bootleg shirts, become the iconic image of Big Poppa.
2. Eric B. & Rakim 'Paid in Full' Album Cover (1987)
It’s only fitting that one of the freshest hip hop debuts of all time comes with an equally fresh album cover. With the DJ/MC duo rocking matching velour suits, exorbitant amounts of gold and standing in front of a backdrop made of cash, Eric B. and Rakim set the tone for a new age of hip hop. This era would move beyond the somewhat silly flows of the late 70’s/early 80’s, introducing serious themes, hard beats and braggadocious rhymes. Their influence in the world of fashion would be just as huge. As put by Eric B., “We made all of that Fendi, Louis Vuitton, Gucci cool. Black people didnt do all of that [before us.]”
1. Run-D.M.C. "My Adidas" (1986)
There was nothing exclusive about adidas shelltoe sneakers when Run-D.M.C. immortalized them in song. Quite the opposite, in fact: the sneakers were was simply classic street attire, preferably rocked with no laces and the tongue blown out—unless you were a true B-Boy, in which case you'd lace ’em up before getting busy on the floor. As with all aspects of Run-D.M.C.'s around-the-way style, the universality was the whole point. According to D.M.C., the group's manager Russell Simmons was high on dust when he ran up on them and shared his vision that they should record a whole song about their kicks. Like so many genius ideas, it was so obvious, nobody had thought to do it before. But as soon as DMC rhymed, “We make a pretty mean team, my adidas and me,” everybody knew it was a fact. Fast forward to a show in Madison Square Garden, Run-D.M.C. is performing the tune and asks everybody in the house to hold their adidas up. A sneaker exec in attendance is so impressed he soon offers the group a $1 million endorsement deal—simultaneosuly changing both the rap game and the fashion game forever. After that Run-D.M.C. didn’t have to “buy 'em off the Ave with the black Lee denim” anymore. But the rest of us sure did.