Regarding fashion, we often look to the past for some serious inspiration and ideas. One great mind is “History repeats itself,” here, we look at the best of the 90ies fashion for men! This season, the decade has captured back the 90s hip-hop fashion for men essence. 

Designers and stylish gents worldwide are seeing the trend shifting back to the 90ies fashion. 

The ’90s, which was known for its relaxed and easy-going sense of style, produced plenty of awesome trends, many of which have already made a comeback. 90ies fashion had it all Business casual, formal wear, monochrome clothing!

From grunge to boy bands, hip hop, and alternative rock music, the 1990s were a decade of innovative pop culture, evolving technological advances, and fashion trends that covered a wide range of subcultures, niche aesthetics, and mainstream movements.

Hairstyles that have been historically African-American resurged, such as Afros, cornrows, and waves; the latter created via sporting a Du-rag over the head. Eventually, the Du-rag became a hip-hop-style accessory on its own. 

By the mid to overdue 90s, platinum became the choice of metal for hip-hop earrings instead of gold, which changed into frequently studded with diamonds.

With this, we take a trip down memory lane to discover some of the best hip-hop fashion outfits in the 90s: 

Captivating  90s hip-hop fashion for men: 

Snapback Hats 

Hip-hop style entered the market and made headlines in the ’90s, and with it came snapback hats. The look, which became a household of every rapper, soon seemed to be worn by men worldwide. 

Today, these flat caps, which typically feature logos,v still look cool. But remember to wear them forwards or backward instead of to the side.

Much of the fashion in the ‘90s was inspired by the music of the time, including the classic snapback hat, which came along with the increasingly mainstream hip-hop style. 

They often featured logos or statements, and the snapback’s popularity among star athletes of the ’90s makes them an unbeatable retro piece.

90s hip-hop fashion for men

Hip-hop style entered the mainstream in the ’90s, and with it came snapback hats. The look, which began with rappers, soon seemed to be worn by men worldwide. Today, these flat-brimmed caps typically feature logos and can still look cool. But remember to wear them forwards or backward instead of to the side.

What made the snapback so unique amongst other hats was the design. The brim was slightly curved, and the hat itself sat high on the head. It goes its name from its adjustable back, which “snaps” in place to the desired size.

The Snapback was made popular by NBA players and the hip-hop group NWA. The most notable snapback was the Chicago Bulls snapback worn by Jordan as he clutched his 6th NBA championship trophy. Another notable snapback was the LA Raiders snapback worn by NWA.

Snapback hats were a popular trend in the 90s and were usually complimented with retro styles like vintage jerseys.

The Bandanas 

Throughout the ’90ies, many different subcultures wore bandanas. Most famously, they were worn by rappers to represent their gang affiliation. Tupac made this look DOPE. However, this look soon became a huge hit and was picked up by the masses and worn simply as an on-trend accessory.

In the 1990s, bandanas appeared in many unique subcultures and niches. First adopted by hip-hop artists and grunge musicians, the bandana can be worn around the head, neck, arm, or even through a belt loop. Versatile yet classic, the bandana became a mainstream accessory.

90s hip-hop fashion for men

Throughout the ’90s, many different subcultures wore bandanas. Most famously, they were worn by rappers to represent their gang affiliation. However, the masses soon picked up this look and wore it simply as an on-trend accessory.

Although countless rappers and singers wore the bandana (in its traditional way and in the style Tupac is wearing in this photo) back in the 90s, it was certainly Tupac that made it iconic. As the 90s ended, so did the bandana’s popularity. In recent years, they’ve only started to crop up again on people’s heads, but more so on women than men this time. 

Kangol Caps 

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 of 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 an around-the-clock crack house in New Jack City.  Throughout the film, Brown and several of his members can wear Kangol caps with the brand’s logo proudly displayed.

90s hip-hop fashion for men

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.

Back in the late 1990s, Kanye West was just one of the many rappers that paired their baggy t-shirts with a bucket hats. After collecting dust at the back of some rather large rap wardrobes for the last few decades, loads of artists, particularly Chris Brown, have revived the look.

Baggy Jeans 

When it came to jeans in the ’90ies, the rule was; the baggier, the better. These supersized pants were a must-have of the day and quintessential to any streetwear look. They were also worn low on the hips and often accompanied by branded undergarments and a chain with a Velcro wallet attached to the end.

90s hip-hop fashion for men

Baggy jeans became an iconic men’s style during the ‘90s. By the middle of the decade, this look had caught fire and moved out of the underground and niche subcultures of skaters, punks, and rappers and into the mainstream. If you want to add some flair to your wardrobe, baggy jeans will do the trick.

At that time, jeans were the whole “religion.” You weren’t in the trend if you didn’t own a pair of blue baggy jeans. Those were often matched with bright color sweatshirts and white sneakers.

The baggy jeans became the real quintessence of streetwear and were worn on a lower hip.

Denim on Denim

During the 90s, urban brands such as Karl Kani, Rocawear, Ecko Unltd, and Johnny Blaze noticed the shift from denim being worn for workwear into a fashionable item. The urban spin came in the form of baggy and oversized Denim pants and jackets.

Subcultures such as punk rock had adapted denim into their culture in the 80s, and Hip Hop began to do the same when RUN DMC introduced streetwear to the masses.

Often styled with timberland boots or Lug boots, the denim looks in the 90s became another affordable look for black kids in the inner cities.

hiphop 90s fashion men

Denim jeans might be a fashion staple today, but that wasn’t always the case. By the 1980s, denim jeans had evolved from workwear to fashion, spawning a new generation of designer denim firms.

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.

Britney Spears and Justin Timberlake are the King and Queen of denim on denim, no one can forget that famous photo of them from back in the day, and no one would ever try to take that title away from them. 

But hip-hop had its handful of denim-on-denim lovers, including Hov, who often rocked the look. After getting a bad name for itself for quite a while, the people that can pull it off are wearing it well this side of 2010.

Timberland Boots 

First on the list and arguably the pinnacle of 90s Hip Hop Fashion is the iconic suede boot that carries heritage and history associated with the culture.

The origin of the boot can be traced back to the 90s as virtually every rap artist from the east coast has worn the boot, from Jay-z, Biggie Smalls to Mobb Deep.

Though initially intended for construction workers, the boot became popular amongst New York drug dealers to withhold bad weather conditions. With the vast majority of drug dealers and hip-hop artists growing up in the same neighborhoods, upcoming rappers would be influenced by the look and place of the boot within hip-hop culture.

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. 

hiphop 90s fashion men

The shoes were designed for construction workers, but New York heroin dealers used them to keep their feet warm and dry during long street shifts. Biggie, Tupac, Nas, Aaliyah—almost every hip-hop and R&B artist—wore Timberland boots.

When you think of the Timberland boots, you think of New York; when you think of New York, you think of Biggie. Yes, New York made “tims” a thing in the 90s as they were rocked by many, not all, New York artists, including Biggie, Nas, Jay Z, etc. 

Although the shoes were made for construction workers working outdoors, it was made notoriously (no pun intended) amongst drug dealers who needed durable and comfortable shoes to wear during long hours on the streets. The shoes have evolved as a fashion statement and are now worn by many, young and old.


This particular style is evidence of how experimental fashion was in the 90s, with the dungarees being something mostly worn by artists opting for a cool comfy look. Like the timberland boots, dungarees were made for workers to act as protective working garments. However, 90s Hip Hop artists turned this into a fashion statement.

The dungarees were popular during the 90s through prominent artists such as Will Smith, 2 Pac, The Fugees, and TLC.

male 90s hip hop fashion

Of all the weird and wonderful styles that the ‘90s produced, the popularity of denim dungarees, however welcome, is probably the 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. Since then, they have consistently released at least one pair every season, further solidifying the influence and popularity of the ’90s trend.”

If you lived through the ’90s, the chances are that you wore overalls. These sleeveless denim jumpsuits were an essential fashion item for the decade and were worn by ladies and gents everywhere. No longer just for farmers, the ’90s made overalls a casual and comfortable wardrobe staple. To rock this look in pure ’90s style, pair classic blue overalls with a crop top and sneakers.

Final Words

Aside from being regarded as the golden era of Hip Hop Music, the 90s also set precedence and tradition for how we dress today‘90s nostalgia has been driving the fashion scene for several years now, and ‘90s hip-hop fashion has been central to that revival.