Like the 80s, the 90s were still about innovation and the introduction of new trends. From Versace to LA Raiders gear to a rap group logo that became a major fashion statement and a clothing label. The 90s were about groups and cliques, with members who had their own unique style. The decade also made 20s-era prohibition gangster fashion totally dope. Again.
NWA's style wasn't particularly memorable in the Slick Rick sort of way. They wore the gold chains made popular by Big Daddy Kane and Slick Rick in the 80s, but (from a fashion point of view) they will forever be remembered for starting simple and casual trends like t-shirts, crewnecks, flannels buttoned all the way up, snapbacks, and jeans. They also made it really cool to wear LA sportsgear like LA Raiders (the Raiders were in Los Angeles from 1982 to 1994 before heading back to Oakland) snapbacks and jackets. Through their style, they repped the West Coast proudly paving the way for guys like Snoop Dogg.
Snoop's style has certainly transcended through time, but it was born in the 90s. Along with Tupac, Snoop reinvented the 20s Prohibition-era gangster style: double-breasted suits, alligator shoes, silk shirts and fedoras.
But before Snoop flat ironed his hair and donned crisp suits, before he was a gangster, he was a gangsta. He took the NWA's West Coast style and added his own preppy touches. A typical outfit included a large button down flannel, Dickies with the cuff and the crease, a pair of Chucks, Nikes, or Jordans, and a flat bill cap.
Fans loved Snoop's West Coast preppy style so much that he wore a Tommy Hilfiger rugby shirt on a 1994 episode of Saturday Night Live and Tommy's sales exploded. Snoop Dogg gave Tommy's label street cred, sending the message to young men everywhere that Tommy Hilfiger was cool.
And we can't forget Snoop's hair, that was its own fashion accessory from cornrows to braids to perms to flat irons and back to braids. Not many guys could pull off pigtail braids the way Snoop could.
We've seen many artists' styles evolve through time, but not many have been as drastic as Snoop's. In the span of just a couple years, Snoop traded in the flannels, braids, and baggy pants for fancy suits, gator shoes, a flight iron, and a fedora. Whether Snoop was wearing a flannel and braids or a suit with a fedora, he always had that West Coast swag.
3. Bad Boys
Biggie, Puffy, and Ma$e all had style for days. With Versace shades, Coogi sweaters, and shiny suits, The Bad Boys had great individual style which also complemented each other very nicely. Biggie contributed to 90s fashion with Versace shades, colorful Bill Cosby-esque Coogi sweaters, Kangols, fedoras, suits, and so much more.
Puffy or Puff Daddy or Diddy, whatever you wanna call him, joined Biggie in making Versace and other designer labels cool and stylish. Together, the two were extremely instrumental in ushering in hip-hop's glamorous image.
In a way, one could liken Puff's style to that of Slick Rick's, going from classy to gaudy. The difference is, Puff Daddy was either classy OR gaudy while Slick Rick did both all at once. Puff could take a Versace suit and shades, leather pants, a Starter jacket or shiny suits and jerseys and still look stylish and put together.
Puffy founded his own clothing line, Sean John, in 1998. He is one of hip-hop's biggest style icons of all time.
From a fashion standpoint, Ma$e is probably most remembered for the shiny suits and jerseys he and Puffy wore in the "Mo Money Mo Problems" and "Can't Nobody Hold Me Down" videos respectively. In music videos, he and Puff often matched, and while their style was a little extreme, it served its purpose. In fact, the Shiny Suit Era ran for five years. It became so big, it was its own era. Like some other hip-hop fashion trends, shiny suits certainly aren't timeless, but they definitely helped define an era of more money, bigger music videos, and flashy clothes, and somehow, Ma$e actually made them look good!
Ma$e and Puff often dressed like twins, at least for videos, but let's not forget Ma$e's style. The white-on-white Air Force 1s, the puffy Northface, the Jesus piece, the hats...Often overlooked, Ma$e was definitely one of the most fashionable rappers of the 90s.
Simply put, the Wu-Tang Clan logo became its own iconic fashion statement, and grew to be so popular, it would lead to the creation of Wu Wear, the first of many clothing lines started by rappers. That alone gets the Wu-Tang Clan a spot on this list. Wu Wear was born in the mid-90s, but even today, men and women are rocking the iconic logo on everything from hoodies, jackets, t-shirts, and hats.
The group had its own fashionable rappers like Raekwon and Ghostface Killah. The rappers put Wallabees on the map. Ghostface even graced us with custom dyed Wallabees. Raekwon rocked the buttersoft leathers and sheepskins, and the Wallabees, but none of us will ever forget that "Snow Beach" Polo pullover he wore in Wu-Tang's "Can It All Be So Simple?" video.
Ghostace was definitely influenced by guys like Slick Rick and Big Daddy Kane, rocking the oversized accessories, but making the look his own with that gigantic eagle piece bracelet. His other contributions to fashion included knit hats and bathrobes, and of course those dip-dyed Wallabes. It's important to consider how much his style has evolved. When Wu first debuted he wore a stocking cap over his face, but over the years, he would go on to become one of the most fashionable rappers in history.
But while Raekwon and Ghostface were super stylish, they aren't the reason Wu-Tang is ranked #2 on this list. It's the iconic logo that so many of us are still rocking today.
Tupac was close friends with Gianni Versace. He absolutely loved dressing him, making him custom-tailored clothes. Tupac even modeled a gold suit at a Versace fashion show in 1996. Gianni Versace and Tupac have been described as "BFFs." A$AP Rocky has even said that Versace viewed Tupac as "the most beautiful man."
Tupac was definitely a style icon. Before he was a Versace model, he was rocking snapbacks, beanies, throwback jerseys, and no one will ever forget the bandanna tied into a headband-- that is perhaps how most of us imagine 'Pac when we think of his name. He stood out in the film Above The Rim in that unforgettable orange leather jacket.
Tupac's style took a more glamorous turn in 1995 with the velour shirt and snakeskin belt. In 1996, he and Snoop ushered in the 20s Prohibition-era gangster style. Whether he was wearing a bright denim jacket, a throwback jersey, or a double breasted suit, Tupac could pull off any look because he had swag. He helped remind us that style is about more than just clothes and shoes. It's a state of mind.
Honorable Mention: Will Smith
We couldn't keep Will Smith off this list, as his role in "The Fresh Prince of Bel-Air" gave him a huge following and cemented himself as a fashionista of sorts. His role as the Fresh Prince definitely helped curate what would became his staples-- colorful clothes (whether that be windbreakers, t-shirts, button downs etc), vests, snapbacks, Nike Air Forces and a high-top fade not only accurately sum up Will Smith as the Fresh Prince, but the general style of the '90s.