20 Ways Hip-Hop Style Was Different 20 Years Ago

Image via Complex Original

While today BAPE and hip-hop style are synonymous, in 1993, the brand was actually just starting out. Learning the ins and outs of design under streetwear legend Hiroshi Fujiwara, Nigo opened up his shop Nowhere in 1993, and then started his own line shortly after. It would take a decade or so before it blew up, creating a near-insatiable desire for Air Force 1-inspired kicks, cartoonish graphic tees, and all-over print hoodies. And if you needed even more proof that Biggie Smalls was ahead of his time--he was spotted wearing the brand as early as the mid-90s.

Before he was getting custom pieces from Riccardo Tisci, Jay-Z's original style choices fell well within the realm of classic hip-hop style: Champion shirts, team caps, and white tees. Hell, no rapper was wearing Givenchy. That's because Givenchy's current menswear incarnation didn't even exist until iconic designer Ozwald Boateng was brought on in 2003, creating tailored cuts and suiting. It wasn't until spring 2009 that Riccardo Tisci brought the dark, gothic aesthetic that informed his womenswear to the men's line. Sup, rottweiler tees?

These days a new collabo drops practically every other day. Back then, it was a very organic process. When Stussy opened its first New York store in 1990, it had already begun to build a cult-like presence with people all over the world. This particular Carhartt jacket came about through mutual friends at Stussy and Tommy Boy Records, just two minds coming together and thinking "wouldn't it be cool if we made this?" Today, collabos are all but expected in the streetwear world, with larger brands and smaller brands trying to build off the cachet of the other's name, whether it's to build exposure or strengthen street cred. Back then, it was just about making cool shit with your friends.

Streetwear still existed, it just wasn't called "streetwear" yet. And it was a very, very different market than it is today. Prior to the rise of rapper-owned labels in the late '90s (word to Sean John and Bushi Sport), Russell Simmons entered the game with Phat Farm in 1992, while X-Large held it down in California as early as 1991. Before that, brands like Triple Five Soul and Cross Colours had been developing a more urban following since their debuts in 1989, and a little brand called Ecko Unltd. started in 1993. Of course, all the cool guys were copping their gear from the Stussy store in SoHo, but the fit and graphic sensibilities were totally different from what they are today.

Shortly before the rise of Lil' Kim and Foxy Brown, female rappers were not as racy as they are today. No disrespect to Nicki Minaj and her contemporaries, things were just different then. Female emcees like MC Lyte, Da Brat, Lady of Rage, and Missy Elliott not only personified the braggadocio and confidence of their male counterparts, but also tended to dress like them too. The same goes for a group like TLC—tall tees, baggy pants, Timberland boots, and bandanas featured heavily into their wardrobe.

Camo and military-influenced clothes played a huge part in hip-hop style 20 years ago. Thing is, they weren't overpriced interpretations from designers or designed by maharishi (Hardy Blechman kicked that off in 1994) or A Bathing Ape (founded by Nigo in 1993). Nope, this was just standard-issue gear bought for cheap at surplus stores. It was rugged, looked cool, and made you look tough, not trendy.

Dropping their debut album Totally Krossed Out in 1992, young rap duo Kris Kross rode the success of their hit single "Jump" to a couple of other memorable jams (sup, "I Missed The Bus?"). Their trademark backwards clothing became such a '90s trend that Warner Brothers started manufacturing a double-sided T-shirt depicting Bugs Bunny and the Tasmanian Devil decked out in about-faced gear, immortalizing the style. The style gimmicks of the time were affordable, yet still served the purpose of getting people some recognition—from Left Eye's condom eyepatch, Kris Kross' backwards gear, Flavor Flav's signature clock, and Humpty Hump's signature eyewear.

Nowadays, the best-dressed rapper is decked out in head-to-toe designer clothing, limited-edition sneakers, and perhaps even all gold everything. Twenty years ago, it didn't matter how fresh you looked—after all, kids were getting killed for their gear. What got you more street cred was a rugged look that befit the type of guy who was unfuckwittable and could hold his own in a brawl. 

Rappers like Das EFX, Spice 1, Fu-Schnickens, and Grand Puba all had pretty out-there hairstyles. The flat-tops and pineapple-like dreads of the late '80s were still around, while '90s Caesar cuts were slowly seeping into album covers and music videos. It was definitely an interesting time to be a rapper's barber.

East Coast skateboarding culture came into its own in '90s New York, influencing the future landscape of streetwear for years to come. What NYC lacked in empty pools and year-round sunshine it made up for with grit and a more aggressive, fuck-you attitude. While skaters like Harold Hunter and Jahmal Williams listened to rap, brands like Stussy and Zoo York were popular with downtown skate rats and rappers alike, and the Beastie Boys embraced a cool, skater-friendly aesthetic from day one, it would be decades before guys like Pharrell Williams and Lil Wayne readily embraced skate culture and learned how to ollie.

Brands were aware of the following that rappers were bringing to their products, but while some try (and still do) to stray away from that audience, labels like Cross Colours aimed specifically at the urban market. Athletic brands like Starter, who was already huge in the '90s, enlisted guys like DJ Jazzy Jeff to model their gear, resulting in some of the best hip-hop fashion ads of all time. Drink companies like Coke caught on, enlisting guys like Kris Kross for Sprite ads.

Today, it's a marketing demographic that's been boiled down to a science. Graffiti-style typefaces and mock-rap beats are engineered to give commercials and products street cred. It's a world where Rap Snacks exist and Nas is doing Gap ads—which is why it's such a breath of fresh air that rappers like Kanye West and A$AP Rocky are helping to redefine hip-hop style for a new generation. They're making sure the sartorial vernacular of the medium is defined by the culture, not stereotypes.

Believe it or not, six-inch wheats were actually selling better than His Airness' signature kicks. While Jordan entered his first retirement in October 1993, Timberland was raking in the cash—about $296 million to be exact. How coincidental: Around this time hip-hop's golden era had adopted the footwear staples as a sure sign of ruggedness and street cred.

Tupac Shakur and Naughty By Nature's Treach were among the only rappers who were recognized for their ink. At the time, not many rappers had tattoos, and the gap between the worlds of tattoo art and hip-hop was for the most part, a chasm. Today, many rappers are seemingly covered head to toe in tattoos. Hell, Pharrell got so tired of the ones on his arms, he had them lasered off.

These days, you'll find dudes like Kanye West and A$AP Rocky getting VIP treatment and prime spots at fashion weeks all over the world. Twenty years ago, that just didn't happen. Sure, some rappers rocked high-class brands, but that's because they had the money to buy them, and weren't friends with designers or had publicists that peddled their celebrity influence to PR agencies.

Slim-fit? No way! The bigger the better. The skinny dudes struggling to find an extra-smedium today would be the same guys scrambling for a XXXXL in the ’90s. You wanted to look like you were almost swimming in your clothes. Now, it's all about finding things that actually fit.

Although there was a huge boom in the late ’90s and Russell Simmons started Phat Farm in 1992, brands like X-Large and Naughty by Nature's Naughty Gear led the charge for clothing lines owned by rappers. Back then, most rappers with style rapped more about wearing clothes than peddling them. Guys like Biggie, Tupac, and Ghostface rapped about Versace, Armani, and Polo, not about how the Yeezys jumped over the Jumpman.

These days, it's assumed that any rapper that blows up and becomes a style icon eventually starts his own line—look at Lil Wayne's TRUKFIT and Kanye West's unreleased Pastelle line and polarizing womenswear collection.

Regional style was a bigger influence on what rappers wore more than fashion trends. Where you were from was where your style was at. Snoop Lion? Nahhhh. When Snoop Doggy Dogg dropped Doggystyle in November '93, he wore a bunch of Cali style staples like flannel shirts, Chuck Taylors, and shirts buttoned all the way up. Same goes for guys like Dre and Ice Cube. Rappers in New York preferred warm layers like Triple Fat Goose jackets, bubble vests, and Carhartt gear. Style was just as territorial as the music.

If you needed more proof that Kanye West was a style game-changer, it had to be when the Air Yeezy was the first Nike shoe made for and designed by a non-athlete. In the ’90s rappers loved Nikes and Jordans all the same, but they weren't one of the cooks in the kitchen.

'Lo Heads had been eating up designer Ralph Lauren's aspirational take on American sportswear since the '80s, coveting gear like Polo Bear sweaters and goose down jackets emblazoned with images of skiiers. But 1993 also saw the introduction of Polo Sport, which became one of the '90s most memorable lines until the early 2000s. A sportier take on Ralph Lauren's usual preppy gear, it helped inform the design of the blue label collection, which shifted towards bubble jackets and anoraks rather than sportcoats and cricket sweaters.

In 1993, Ralph Lauren enlisted black model Tyson Beckford to be the brand's face, an inadvertent nod to the burgeoning demographic of young 'Lo fans. A year later, when Raekwon rocked the now-infamous Snow Beach jacket from the designer's Cold Wave collection in the video for "Can It Be All So Simple," people flipped. It sort of legitimized these cult pockets of Polo diehards, while at the same time causing many kids to see what he was rocking and instantly go, "Yo... I NEED THAT." 

Wanna dress like Kanye West or Jay-Z? You'll max out your credit card fast. In the '90s, while rappers name-checked certain luxury brands, you'd still find them in gear from Carhartt, Timberland boots, and Dickies. A lot of California rappers readily embraced Chuck Taylors, which were a lot easier to get than limited-edition Jordans or $400 Margiela kicks. Carpenter jeans and surplus peacoats? Those might have required a little saving up, but they were still easily attainable, and definitely not as exclusive as a lot of the high-end, obscure Japanese brands guys like Lupe Fiasco prefer to rock today.