by Tom Stratton

Biggie Smalls - The Looks & Brands

“I put hoes in NY onto DKNY / Miami, D.C. prefer Versace / All Phi...
Biggie Smalls - The Looks & Brands
Biggie Smalls was ahead of his time in many ways, his intricate laidback flow, laid over soul and jazz beats, made him an absolute trailblazer and one of the best emcees of all time but it was also his fashion sense that made him the icon he is today. It’s become commonplace for rappers to attend catwalk shows and mix with the fashion elite but B.I.G was doing this (along with Tupac) in the early 90s. He was even friends with Donatello Versace. This mix of haute couture with the former-drug-dealing, 300lb Brooklynite, turned out to be an inexplicably perfect mix and we can still see Biggie’s style impacting fashion styles right up to this day. Kanye may well have ventured into his own fashion brand and infiltrated the catwalks but it was The Notorious B.I.G. who made it seem possible in the first place.

“I put hoes in NY onto DKNY 

Miami, D.C. prefer Versace 

All Philly hoes know it's Moschino 

Every cutie wit a booty bought a Coogi”

Biggie knew his brands and he knew what he liked. With an eye for style he would constantly namedrop brands, just like Run-DMC had done with “My Adidas” years before. Biggie just took it that step further, his style was like his flow: thought out, impressive, and just seemed like it came so easily. From his early street style, to catwalk shows, to the Godfather style he came to adopt, Big was the don of high fashion and hip hop. Lets take a look at some of his (and our) favourite looks.

Those Versace Shades

Biggie made these limited-edition Medusa Versace sunglasses look so good that Versace released another limited edition range inspired by the man himself’s in 2018. Donatello Versace praised Big for making Versace a household name and you can see why. Plenty have tried since but I can’t think of many who makes that iconic gold Medusa look so effortless cool. They’ve even distracted from the beautiful silk shirt he’s got on. 

Silk Shirts 

Here’s Big wearing a loud print silk shirt underneath his trademark shades. Dripping with relatively subtle gold jewellery he manages to make this silk number look somehow not too over-the-top. Not only did he know how to dress but he definitely had an eye for accessorising. 

Kangol 504 Wool Cap

Paired here with another of his iconic looks (which we already devoted a full piece to) Biggie was rarely seen without his Kangol 504 wool flat cap. There’s many who’ve tried but not many who’ve been able to pull it off like Chris Wallace could. Another effortless mix of streetwear and high-end fashion, as was his whole look. Street kid to fashionista, who’d have thought it?

Karl Kani

Again showing his love of streetwear, Biggie advertising the height of streetwear fashion Karl Kani. Karl Kani really was the go to streetwear brand for hip hop heads and Biggie was often seen rocking it. Who rocks Karl Kani and is friends with Versace? Biggie, that’s who. 


Biggie’s friend, stylist Groovey Lew, said that when Biggie discovered the famous Coogi jumper he was all about army jackets. All the street kids in the 90s were about army jackets but Big wasn’t just about any army jacket. He found Japanese designer BAPE, or rather designer NIGO found him, knowing it would make his distinctive camo print famous (just as it had the Coogi). Biggie was a promoter through and through.

Homburg hat

He would never fully abandon his Kangol 504 but during his prohibition mafioso inspired stage Biggie absolutely owned wearing a homburg hat. There’s only really Biggie who could’ve got away with it; pairing it here with another Versace shirt, it was usually on top of a white or pinstripe double-breasted, three-piece suit. The mans style was as versatile as his raps.

Polo Necks 

Absolutely as crisp and fresh as his rhymes, Big was rocking the polo neck and somehow making it look like the most ‘now’ thing to have in 1995, when in reality they’d had their time. Accessorised perfectly again - another one of those homburgs and a large encrusted crucifix set off the white against that thick, black, double-breasted blazer. It’s like he’s got four different eras, put them all together, and found the perfect combo. 

Coogi Sweater 

I wasn’t going to include this as I’ve written another article entirely dedicated to Biggie and Coogis but how could I not include it? Just look at it, I don’t even have to say anything else, just… look at it!