This week marks 20 long years since Christopher George Latore Wallace, better known to the world as The Notorious B.I.G., released Ready To Diean album still considered by many to be one of the greatest hip-hop records ever made. While the man himself was snatched way before his time, his sizable imprint on the world lives on in ways not even he could’ve imagined. Sure, everyone knows rap music will forever bear the echoes of his inimitable flow (click here for some of his best moments), but today we want to honor something just as important: his sense of style.

Streets ahead of the game on so many levels, Biggie made some bold wardrobe moves in his day. But how many of them have stood the test of time? Here are 10 of the big man’s greatest fashion moments, along with our verdict on whether they’ve enjoyed Life After Death or whether they too were Ready To Die.

 

Image via The Gentleman’s Daily

 1. COOGI Sweater

Then: If there was one item that could be said to embody Biggie’s style legacy, it would have to be the COOGI Sweater. This niche knitwear manufacturer from the depths of Australia (well, Melbourne) was originally marketed at the country club-attending, yacht-pushing upper crust, but Big had other ideas. Much like the inner city gangs of Polo Ralph Lauren fans springing up across New York at the time, he claimed the COOGI for a whole new market, recognizing the impact potential of its outrageous color scheme and high price point. And, just like that, a legendary look was born.

Now: Thanks to a surging wave of ’90s nostalgia and some powerful celebrity backers, right now the COOGI sweater is enjoying a popularity it hasn’t seen since the days of “Juicy.” Everyone from Drake to Hit-Boy to the A$AP Mob has been spotted rocking those rainbow threads of late, and the brand itself recently relaunched with an eye on reclaiming some of its elite status after a mid-’00s lull.

Verdict: Life After Death

 

Image via IMGArcade

2. Versace Shades

Then: Another of his trademark items, Biggie was rarely seen without a pair of Medusas on his temples. Unlike the folks at COOGI, however, Donatella Versace has publicly praised B.I.G. for his role in bringing the once fearsomely exclusive fashion house to people on the street. In fact, many would say those black and gold frames have never looked more at home. Biggie, on the other hand, stepped right out of his natural environment to become one of the first hip-hop stars (along with Tupac) to regularly attend Versace’s runway fashion shows – a trend that has since become the norm.

Now: Perhaps unsurprisingly (given how close he was to Biggie), Sean Puffy Combs has long found space for Versace in his sunglass collection. More recently, however, artists like Tyga and 2 Chainz have made an effort to revive the trend. Whether they pull it off quite as well as Big Poppa is a matter of personal opinion…

Verdict: Life After Death

 

3. Turtleneck Sweater

Then: In the wake of the ’70s, the turtleneck sweater had been suffering a serious Starsky & Hutch hangover. For many, it was the stuff of fulsome beards, Scandinavian knitwear models and corny Christmas cards; then Biggie got involved, paired it with a double-breasted leather overcoat and those Versace rims and suddenly it made a whole different kind of sense.

Now: Let’s just say it takes a very special kind of person to be able to rock this one well. Jay Z has dabbled in those dark arts on occasion but, for the most part, once Steve Jobs got in on the action, the turtleneck was about as hip hop as a pair of mittens.

Verdict: Ready To Die

 

4. BAPE Camo

Then: Back in the early ’90s, if you wanted camo, you went to an army surplus store. Gangsters and hip-hop artists alike sought out their own menacing, military aesthetic, but no major streetwear brand had yet realized the potential for making it a part of their own creative direction. There was, however, a young, hip-hop obsessed designer from Japan by the name of NIGO who saw that trend coming a mile off. Through sheer dogged determination he managed to get one of his pieces into Biggie’s hands, and the rest, as they say, is history.

Now: Is BAPE still around? Do pigeons still drop shit?

Verdict: Life After Death

 

Image via Disposed Mind 

5. Kangol Wool 504

Then: The third piece in the “Trifecta Of Biggie Smalls,” the Kangol Wool 504 Driver’s Cap is yet another item that found itself transported from a world of mild-mannered respectability into another one entirely, thanks to some sharp-eyed ghetto tastemakers. While a handful of rappers in the 1980s had picked up on the brand (most notably LL Cool J), Biggie’s sheer size seemed to fit the distinctive, stiff-brimmed headwear so perfectly that the flat cap became an inseparable part of his image.

Now: Perhaps it’s because it suited him so entirely, no rapper has since come close to pulling off the Kangol like Big did. Ever in his shadow, anyone who’s tried to rock this look since has just looked like a kid dressing up in daddy’s clothes.

Verdict: Ready To Die

 

6. Jesus Piece

Then: While a certain amount of discrepancy exists over whether B.I.G. was the first to rock the infamous Jesus piece, he was certainly among its earliest adopters. Having purchased three of the diamond-encrusted necklaces from jewelry designer Tito as a present for himself, Lil’ Cease and best friend D-Roc, he was frequently pictured rocking his in public and even name-dropped it specifically in his late hit I Love The Dough

Now: The unprecedented resurgence of the Jesus Piece is one of the greatest phenomena in hip hop today. Around 2004, Kanye West decided enough time had passed for it to warrant a comeback, and since then every rapper and his grandmother has been in on the action – from The Game naming his latest album after one, to Rick Ross donning ten of them on his own LP cover, to Macklemore even braving the look. With scores of cheap replicas flooding the market, the Jesus Piece has truly become the Louis Vuitton handbag of hip hop (click here for the real deal).

Verdict: Life After Death

 

Image via XXL

7. Cane

Then: Less an objective fashion choice, more a medical necessity following Biggie’s near-fatal car crash in 1996, the cane became an obligatory part of his wardrobe. Still, silver linings don’t come much more stylish. Coinciding with a move towards a more overt, 1920s-inspired gangster aesthetic – all three-piece suits and homburg hats – the cane was the ultimate mafioso accessory. And, of course, Big pulled it off like he’d been born with one.

Now: As a staple of 1970s and ’80s “pimp culture,” the cane has struggled to find a place in modern-day hip hop as few of today’s artists feel that image is still exciting or relevant. Nate Dogg was perhaps the last major proponent of the cane as a style accessory and with his passing it seems destined to be seen more as a costume prop than a credible wardrobe choice.

Verdict: Ready To Die

 

Image via GlobalGrind

8. Versace Shirt 

Then: Biggie’s fondness for the Italian fashion label didn’t stop at sunglasses. Immortalized in that infamous “Hypnotize” video, the sight of Biggie in flamboyantly patterned flowing silk became a regular occurrence, ushering in a new wave of “refined style” to the world of hip hop. Unaccustomed to clients his size, the folk at Versace had to tailor many of Biggie’s signature pieces specifically for him to wear. This level of couture service for a rap figure was unprecedented, and showed real foresight in terms of fostering a bond between the two – something that helped pave the way for Versace’s eventual expansion into streetwear (without which we wouldn’t have these).

Now: Biggie (and Tupac, it must be said) helped open the door to a love affair with Versace that has since showed little sign of cooling down. Puffy, Big Pun, Rick Ross, Kanye, Drake, A$AP Ferg, 2 Chainz – the list of rappers to have donned that silk is longer than a McDonald’s lunch line.

Verdict: Life After Death

 

Image via MTV

9. Homburg Hat

Then: As mentioned earlier, Biggie’s latter-day move towards his Frank White, Kingpin-styled crime boss persona brought with it a change in wardrobe direction. While his beloved Kangol was still a part of his repertoire, it was increasingly replaced by a wide-brimmed Homburg to match the sharply tailored suits he gained a taste for, creating an altogether more mature look to match his larger-than-life personality.

Now: Once the cornerstone of Run DMC’s signature outfit, these days only a handful of hip-hop artists will go anywhere near the Homburg/Fedora hat. Wiz Khalifa, Mos Def and Usher have all tried it on for size, but ultimately the number of young, smooth-voiced male pop artists to have made it their thing is enough to consign it to the history books for most emcees out there.

Verdict: Ready To Die

 

Image via Arc Records

10. Crown

Then: The defining aspect of the most iconic Biggie image ever taken – shot by photographer Barron Claiborne for the cover of Rolling Stone – the gold crown is perhaps Christopher Wallace’s greatest ever act of costume flamboyance. While many already considered him a king among emcees, this truly sealed the deal.

Now: Rappers claiming to be kings is just about the most played out cliché in the book, and many have since tried to draw such a comparison for themselves. Lil Wayne is particulary fond of his gold headwear and Kendrick Lamar recently graced the cover of The Source in a direct replica of Biggie’s crown, but it’s clear that anyone making such a connection today has to do so (at least in part) as a tribute to the great man himself.

Verdict: Life After Death

 

Final Verdict: With six out of 10 of Biggie’s signature style moves still living strong, it’s clear not even death could put an end to his trend-setting influence. As a cultural icon, Biggie was untouchable. And if you didn’t know that before, well, now you know…

The quadruple-platinum selling Ready To Die is 20 years old today. If you don’t own a copy, hang your head in shame, then get one here.

Words by AJ Gwilliam
Features Editor

Proud Brit. Pathologically addicted to white trainers (AKA "sneakers").

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