Hip Hop Fashion Essentials

Everything you need to know about 90s hip-hop fashion, from the iconic to the obscure.

90s nostalgia has been driving the fashion scene in recent years and the era’s hip-hop fashion has been central to that revival. Current trends across the spectrum have been mostly dominated by Supreme, the New York skate brand whose formula is largely built on the legacy of ‘90s street fashion – along with Louis Vuitton. But where did it all begin?

To celebrate 50 years of Hip Hop 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 its own individual way.

Timberland Boots

Biggie in Timberland Boots

To this day, the humble suede Timberland boot in its classic tan colourway is known as a staple of New York-style, but its origins can also be traced to ‘90s hip-hop. Initially a product for construction workers, legend has it that 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 – all wore Timberland boots and still do today.

Oversized White T-Shirts

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.”


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, as seen on 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, Supreme have released a pair of dungarees consistently every season.

Premium American Sportswear

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

Labels like Tommy Hillfiger and Ralph Lauren’s Polo Sport sub-line traded on an image of 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-Tan 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.

Sports Jackets & Caps

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. 

Paisley & Bandana Prints

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 colour; the Los Angeles-based Bloods and Crips who wore red and blue, the Latin Kings, a latino gang born out of Chicago who sported black and gold as their colours. Paisley bandanas in each gang’s respective colours were a 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 coloured bandana without connections in certain neighbourhoods of cities like LA and Chicago is widely considered a bad idea, for obvious reasons.

Kangol Bucket Hats

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. Once again, it was Kangol who dominated this style, with their Kangaroo logo regularly featuring on rapper’s buckets of choice.

First popularized by LL Cool J during the ‘80s, British headwear company Kangol’s bucket hats started 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 around-the-clock crack house in New Jack City.  Throughout the film, Brown and several of his members can be seen wearing Kangol hats 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 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.

Luxury Tracksuits

The Carhartt Tracksuit

With high-end designers regularly collaborating with the likes of Nike, Adidas and Puma 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 and Kappa. Tracksuits began appearing in 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.

Military Apparel

Tupac in Camo

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. Artists like Tupac and Biggie made camo part of their wardrobe, and the style has endured ever since.

Puffa Jackets

Another trend born out of street life necessity, insulated jackets by brands like The North Face 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, hoodies and hats.

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

Air Jordans

High-fashion collaborations and luxury sneakers by every fashion house under the sun, we seem to take sneaker culture for granted. Seeing a new colourway drop and resell for hundreds of pounds 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 Jordansneaker 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. 

Champion Hoodies

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 fuelled 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 were 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.

Avirex Jackets

Big, heavyweight, and covered in patches, Avirex Flight Jackets  became part of hip-hop fashion 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.