Getty Images / Michael Ochs Archives

‘90s nostalgia has been driving the fashion scene for several years now, and ‘90s hip-hop fashion has been central to that revival. This shouldn’t necessarily come as a surprise; current trends across the spectrum have been dominated by Supreme, the New York skate brand whose formula is largely built on the legacy of ‘90s street fashion.

Beyond that particular connection, however, the ‘90s as an era is well-known for its wealth of fashion trends. As the last period before the digital world dominated culture, the legacy of the ‘90s is viewed through a rose-tinted lens of CD covers, magazine spreads, cable TV shows and blockbuster films.

Black music groups like Bones Thugs-n-Harmony and Boyz II Men took the aesthetic of ‘90s hip-hop and created a style that influenced virtually every major boy band of the decade, and Hollywood blockbusters like Poetic Justice, Boyz n the Hood and Juice placed black American style on the big screen and created some of the most memorable scenes in cinematic history (as well as some solid acting performances from Janet Jackson, Ice Cube and Tupac Shakur).

For anyone who came of age in the era, just hearing the words ‘90s hip-hop fashion probably triggers a laundry list of reference points and essential pieces, but even then it can be difficult to describe them in words. As for younger generations who are buying contemporary pieces from labels like OFF-WHITE, Palace and Guess, it might be hard to understand the references without first-hand familiarity.

So here’s a brief rundown of the essential ‘90s hip-hop fashion wardrobe, and how each piece came to embody the style of the times in their own little way.

’90s hip-hop fashion unpacked, from the iconic to the obscure.

Kangol Caps

Highsnobiety / Eva Al Desnudo

First popularized by LL Cool J during the ‘80s, British headwear company Kangol became woven into the cultural memory of ‘90s hip-hop after appearing in some the era’s most seminal films. In 1991, Wesley Snipes played Nino Brown, a drug lord who takes over a New York apartment block, turning it into a round-the-clock crack house in New Jack City.  Throughout the film, Brown and several of his members can be seen wearing Kangol caps with the brand’s logo proudly displayed.

A few years later, Quentin Tarantino would follow up his hit film Pulp Fiction with Jackie Brown, an homage to ‘70s blaxploitation cinema starring Samuel L. Jackson as Ordell Robbie, whose back-turned Kangol hat became one of Jackson’s most iconic looks. In fact, so attached was Jackson to the style that he’s the first person most people think of when they think of Kangol hats.

You can find out more about them here.

Timberland Boots

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To this day, the humble suede Timberland boot in its classic tan colorway is known as a staple of New York style, but its origins can also be traced to ‘90s hip-hop. Though intended for construction workers and the like, word is the shoes gained traction among New York’s drug dealers who needed strong, sturdy footwear to keep their feet warm and dry during long hours out in the streets. Biggie, Tupac, Nas, Aaliyah – virtually every hip-hop and R&B artist you can think of – they all wore Timberland boots, and still do today.

Read more about them here.

Oversized White T-Shirts

Highsnobiety / Eva Al Desnudo

From the beginning of the ‘90s well into the late 2000s, hip-hop fashion was largely defined by oversized fits and long silhouettes. One reason cited for this is that many kids growing up poor in cities like New York, LA and Chicago would receive clothes as hand-me-downs from their older siblings. And even if you didn’t have a sibling, wearing oversized clothes might have kept you out of trouble; after all, the bigger your clothes, the bigger your “older brother” must be.

The oversized plain white tee became a staple of ‘90s hip-hop fashion, so much so that when Kanye West collaborated with French fashion house A.P.C. on a capsule collection in 2013, one design was a humble oversized white t-shirt, dubbed the “hip-hop T-shirt.”

Dungarees

Highsnobiety / Eva Al Desnudo

Of all the weird and wonderful styles that the ‘90s produced, the popularity of denim dungarees, however welcome, is probably hardest to place. Fitted or baggy, strapped up or with one undone, styled with T-shirts, hoodies, button-ups or nothing at all, the unexpected trend got a cultural cosign from the likes of TLC, The Fugees, Will Smith and Tupac, and became a staple of the era.

If you wanted proof that we’re going through a ‘90s revival right now, consider that Supreme released a pair of dungarees several seasons back, and have released at least one pair consistently every season since. The force is strong.

Big, Bold Patterns

Other / Barry King / WireImage

As hip-hop began to split into multiple subgenres at the end of the ‘80s, a wide range of styles arose for each respective group. In New York City, artists like A Tribe Called Quest, De La Soul, Queen Latifah and Brand Nubian formed the Native Tongues, a musical collective who promoted pro-black, Pan-African and Afrocentric concepts, positive thinking and spirituality. The group was distinguished by their striking outfits featuring tie-dye, paisley, African wax prints and bright colors.

The style definitely influenced Will Smith’s style in The Fresh Prince of Bel-Air, and endures as one of the most endearing chapters in ‘90s hip-hop fashion, one embodied by pure joy and collective positivity.

Denim

Highsnobiety / Eva Al Desnudo

Denim jeans might be a fashion staple today, but that wasn’t always the case. Adopted during numerous subcultures like punk rock and the flower power movement, by the ‘80s denim jeans had moved from pure workwear to credible fashion garm, heralding a new age of designer denim brands.

By the ‘90s, labels like Guess Jeans, Versace, Moschino and Calvin Klein were leading the way in high-end, fashion-focused denim, while black-owned labels like Phat Farm and FUBU cemented denim as part of the ‘90s hip-hop fashion wardrobe.

West Coast artists like Tupac and Eazy-E of N.W.A. took the style even further, pairing denim jeans with oversized denim jackets for the full ensemble.

Premium American Sportswear

Highsnobiety / Dominik Schulte

One of the biggest stories in American fashion during the late ‘80s was the rise of a new wave of American fashion designers making waves with their American response to a fashion scene that had been largely dominated by European designers.

Labels like Tommy Hilfiger, Nautica and Ralph Lauren’s Polo Sport sub-line traded on a meticulously-crafted image of distinctly American sophistication – think ski slopes, country clubs and weekend yachting trips in the Hamptons. The style struck a nerve with East Coast youth who were already well tuned to the fashion scene, being so close to New York.

When Wu-Tang Clan broke onto the scene in 1993 draped in Polo Sport, it cemented the style’s place in hip-hop fashion history. If you needed any more convincing, consider that many of Supreme’s most popular contemporary designs are directly inspired by designs from those same brands.

Starter Jackets & Caps

Getty Images / Michael Ochs Archives

Considering so much of early ‘90s hip-hop was defined by the East Coast/West Coast divide, it’s no surprise that sports team apparel would become a big part of hip-hop fashion of the era. At the time, this was dominated by American sportswear brand Starter, who since 1983 had official licensing deals with the NFL, NBA and NHL—effectively total dominance of the merchandising market of three of America’s most popular sports.

Their glossy satin jackets and snapback caps became a staple of hip-hop fashion of the era; it’s hard not to think of N.W.A., for example, without thinking of the Los Angeles Raiders. Starter fell out of fashion toward the end of the ‘90s, but its legacy has endured. Supreme often places a flip of the Starter Star logo on the back of its snapback caps as a nod to an OG of ‘90s street style.

FUBU

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FUBU was probably one of the first major brands built with black American youth explicitly in mind, as the phrase contained within the brand’s name (an acronym for “For Us, By Us”) explains.

Started by a young Daymond John (of Shark Tank fame) with three friends, the homegrown hat operation erupted into a global fashion phenomenon grossing hundreds of millions of dollars annually at its peak. By the turn of the millennium, FUBU’s star had begun to fade, but it left behind a legacy that’s deeply interwoven with the culture of ‘90s hip-hop.

Paisley & Bandana Prints

Highsnobiety / Eva Al Desnudo

As its name suggests, gang culture was central to one of the biggest subgenres of ‘90s hip-hop, gangsta rap. More specifically, ‘90s gang culture was defined by three major inner city gangs who each sported a respective color; the Los Angeles-based Bloods and Crips who wore red and blue, respectively; and the Latin Kings, a latino gang born out of Chicago who sported black and gold as their colors.

Paisley bandanas in each gang’s respective colors were a ubiquitous symbol of gang affiliations since their founding in previous decades, and it was no different when a rapper with particular connections gained fame. Since then, the style has spread beyond its original roots, but wearing a colored bandana without connections in certain neighborhoods of cities like LA and Chicago is widely considered a bad idea, for obvious reasons.

Bucket Hats

Getty Images / Ron Galella / WireImage

Another style popularized by LL Cool J in the late ‘80s, bucket hats were equally popular in hip-hop fashion during the early ‘90s, making regular appearances on members of Wu-Tang Clan and EPMD. Once again, it was Kangol who dominated this style, with their Kangaroo logo regularly featuring on rapper’s buckets of choice.

Unlike Kangol caps, the bucket hat style has endured to this day, a popular choice among the rap scene’s more esoteric figures like Earl Sweatshirt and ScHoolboy Q.

Luxury Tracksuits

Highsnobiety / Eva Al Desnudo

With high-end designers regularly collaborating with the likes of Nike, adidas, PUMA and more, it’s easy to take the idea of high-end sportswear for granted these days, but it wasn’t long ago that sports apparel and high fashion existed in strictly separate spheres.

That changed in the late ‘70s and ‘80s with the birth of lifestyle sports like jogging and country club culture, as well as the rise of premium Italian sportswear brands like FILA, Kappa and Sergio Tacchini. Tracksuits began appearing in ostentatious fabrics like velour and silk, with ornate decorative details and a healthy amount of branding.

In fact, it’s possible the luxury tracksuits we see labels like Gucci and Versace releasing today wouldn’t exist if it weren’t for Daniel “Dapper Dan” Day, a Harlem-based designer who created bootleg high-fashion tracksuits for many of hip-hop’s earliest stars throughout the ‘80s. Read more about his legacy here.

Military Apparel

Getty Images / S. Granitz / WireImage

Camo has been a mainstay of streetwear for as long as anyone can remember, and the same is true of hip-hop. In the early years, rap group Public Enemy complemented vocalist Chuck D’s politically-charged raps about the struggles of life as a black person in America with military uniforms in a grayscale woodland camo pattern, signifying their status as soldiers of America’s urban warzones.

The fact that military gear was available in abundance from army surplus stores and was affordable and hardwearing was another plus. Countless artists like Tupac, Biggie and Das EFX made camo part of their wardrobe, and the style has endured ever since.

Wu-Wear

Getty Images / Frank Micelotta

Musicians have always sold simple merch like T-shirts and hoodies, but the phenomenon of artists like Travis Scott and Kanye West selling comprehensive clothing lines is something some of us take for granted. Wu-Tang Clan were one of the first to do it nearly two decades earlier with Wu-Wear. Launched in 1995 by a childhood friend of the Clan, Wu-Wear translated the Wu-Tang Clan’s formidable identity into the context of clothing and created one of the most memorable chapters in hip-hop fashion history.

Coogi Sweaters

Getty Images / Melodie Jeng

Australian knitwear brand Coogi’s distinctive colorful sweaters might only have appeared on one rapper, but the impact was so huge that it effectively defined the label for years to come. Though he might have been best known for his lyricism, Brooklyn rapper The Notorious B.I.G. was also one of hip-hop’s earliest fashion authorities, name-dropping a wealth of brands in his lyrics and wearing labels years before they caught on.

Thanks to name-drops in several of his songs, Biggie helped to popularize Coogi sweaters among black American rap fans, and cemented the brand’s legacy. Need more convincing? Image search “Coogi Sweater” and see who shows up. Now that’s influence.

Puffy Jackets

Highsnobiety / Eva Al Desnudo

Another trend born out of street life necessity, insulated jackets by brands like The North Face and Helly Hansen were a must for anyone planning on spending long hours on street corners in chilly cities like New York or Chicago.

When looking at down-filled jackets as a fashion essential today, it’s important to remember that they were never intended to look good as such; they were designed purely for practical purposes. It was black youth in cities on the East coast who took an essential piece of clothing for their climate and made it look good, just as they did with Timberland boots, Champion hoodies and beanies.

When East Coast rappers rose to stardom, they took the style of their cities with them, and the puffy jacket has been a classic ever since.

Air Jordans

Highsnobiety / Asia Typek

Quickstrike drops, high-fashion collaborations, luxury sneakers by every fashion house under the sun, these days we take sneaker culture for granted. Seeing a new colorway drop and resell for hundreds of dollars minutes later is just part of the culture. But back in the ‘90s, the idea of sneakers as anything more than something for sport was an alien concept.

When basketball player Michael Jordan partnered up with young sportswear brand Nike on a signature Air Jordan sneaker in 1984, the shoe quickly erupted into a national phenomenon. A few years later, Nike spun the series off into its own Air Jordan line, creating possibly the first chapter in sneakerhead culture. Like the classic commercial with iconic film director Spike Lee said, “It’s gotta be the shoes!”

Clark’s Wallabees

Other / Ron Galella, Ltd./WireImage

Clark’s understated suede moccasin shoe might not be the first thing that comes to mind when you think of ‘90s fashion, but whenever you find an element of ‘90s hip-hop fashion that you can’t make sense of, you should probably look to the Wu-Tang Clan.

Members of the Clan regularly rocked Clark’s Wallabees from their early days, and just as the rough and conceptual production of their debut album, Enter the Wu-Tang (36 Chambers) redefined the sound of hip-hop on its release in 1993, their unique approach to dress did the same thing for hip-hop fashion.

Champion Hoodies

Highsnobiety / Eva Al Desnudo

Champion’s return to prominence in recent years might come as a surprise to those of us who knew it as an affordable sportswear brand throughout the early millennium, and its renaissance was undoubtedly fueled by Supreme’s regular collaborations with the brand over the past few years, but like many of the New York skate brands partnerships, there was a cultural significance to the decision. The brand’s distinctive boxy sweatshirts with oversized hoods was the silhouette of choice in hip-hop culture during the early ‘90s, as well as the hardcore punk scene in cities like New York and Boston.

Plaid & Check Flannel

Highsnobiety / Eva Al Desnudo

Hip-hop and grunge might have had totally disparate sounds, but if there’s one thing that united the two musical subcultures, it’s the humble check flannel shirt. A longtime staple of the classic American wardrobe, they were cheap, affordable, versatile, and an easy way to inject a bit of color into an outfit. Wear them oversized or around the waist, but never buttoned up.

Avirex Jackets

Other / Djamilla Rosa Cochran / WireImage

Big, heavyweight, and covered in patches and flare, Avirex’s premium leather flight jackets became part of the hip-hop fashion lexicon partly for their utility, and partly for their aesthetic appeal. They were built to last, kept you warm, styled well with hoodies and jeans, and best of all, looked expensive.

Their impact ended up going beyond hip-hop as well, becoming a statement piece of clothing in the early days of London’s grime scene over in the UK. British skateboard brand Palace even created a collaborative Avirex jacket for Fall/Winter 2017 as a nod to the brand’s cultural legacy.

If you want a deeper dive into the 90’s, watch the video below.

Words by Gregk Foley
Contributor

Gregk Foley is a writer based in Berlin whose work explores the intersections of style, culture, politics and identity.

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