Top 10 Best 90s Hip Hop Fashion Trends

90s hip-hop fashion includes Timberland boots which are also known as Timbs. They are a premier fashion statement from New York.

They are six-inch boots that go up to your ankle and can usually be found in a light brown color. They primarily work as outdoor shoes and function for use in the wilderness and outdoor work.

However, in the 90s, the Timbs started becoming a trend among rappers, especially in New York where it has been worn as a 90s hip-hop fashion male statement by rappers like the Notorious B.I.G. and more. Despite the company never intending it to be a premier shoewear for rappers, it not only became that throughout the decade but persists to this day among rappers in all parts of the United States and beyond. 

The shoe and its brand were originally popular among and designed for blue-collar workers, who found the shoe appealing due to its hard construction and waterproof design. However, drug dealers in New York soon saw an appreciation for the shoe for precisely the same reason as they needed to be out on the streets all night, and could depend on the Timbs to keep them warm and dry. 

As many prominent rappers of the day were either drug dealers themselves or were friends and associates with many, soon enough they followed suit and started wearing Timberland boots themselves. As these rappers grew in fame, so did the music genre’s association with the boots, to the point that nowadays, Timberland boots are directly associated with hip-hop and East Coast, New York hip-hop more specifically.

Denim dungarees are overalls made from denim that were popular 90s hip-hop fashion female outfits. Like Timbs, they were originally for blue-collar workers. 

Seen primarily as workwear, the clothing too started taking the decade by storm through its association with 90s hip hop. Though primarily worn by female rappers, they had male fans and adopters as well. 

What makes the dungarees such a wonderful display of 90s hip hop is that, unlike the Timberlands, this article of clothing has no direct lineage to hip hop like the shoewear. It popped up and became adopted by the entire culture, and has gripped its chokehold in that culture deeper the further we move away from the decade, unwilling to let go.

From conscious acts like The Fugees to more gangsta rappers like Tupac, to even the mainstream darlings like Will Smith and the group TLC, Dungarees were everywhere to be found in the 90s and could be worn in a variety of styles. Whether with a T-Shirt, or hoodie, with buttons on and off, the versatility of the clothing made it a darling for many of the premier fashion icons of the day and has become as big an indicator of the 90s as the Timbs are.

Usually styled with other articles of clothing that were popular in the day, the dungarees are part of a larger obsession that 90s artists had with denim as a whole, which could also come from the fact that many of these artists grew up poor. Denim is a coarse and dependable material that does not wear or tear easily, and as such is a welcome piece of clothing for a demographic of people that don’t necessarily have the funds to buy new clothes whenever they want.

Sports Jerseys and sportswear in general are popular 90s hip-hop fashion outfits. It’s due in fact to the integration of the musical genre and sports. 

Hip Hop has long been synonymous with sports with many rappers using sports terminology to talk about the genre and their place in it. As such, it comes as no surprise that sportswear would become a big part of hip-hop fashion.

Especially in the 90s when the divide between the East and West coast was as big as it ever got, with rappers consistently feuding against each other. As such, they would also wear sports jerseys corresponding with teams from their region to represent their coast, region, or city, as well as make a fashion statement. 

Be they simple sports jerseys that showcased a team or player, starter jackets and caps, or even sportswear in general, this aspect of Hip Hop only added to the furthering of the genre discovering and making a new style all their own. As athletes, especially those from similar areas and upbringing as rappers started getting popular, wearing sports jerseys became a sign of camaraderie.

This is another aspect of 90s hip-hop fashion that has remained present till the modern day, with hip-hop and sports, be it NFL, NBA, NHL, and more still being intrinsically tied together. Rappers still wear sports jerseys, but they will never be as iconic as it was back in the 90s due to the various statements musical artists made with them. 

FUBU is a clothing apparel company that is intrinsically tied to Hip-Hop. FUBU stands for “For Us, By Us.”

What separates FUBU from the previous entries on the list is the fact that it is not an article of clothing but an entire brand. Founded in 1992 by Daymond John, FUBU was the first Hip-Hop apparel company, and as such became an indelible part of 90s culture both in clothing and fashion and in the overall development of the Hip Hop style.

Despite many of the rappers of the day gaining success and sporting clothing and accessories from a variety of popular and opulent brands, FUBU gained more of a standing due to the fact that it was black-owned. As such, rappers and other prominent hip-hop figures of the day could wear the brand proudly, knowing that they were representing their culture and the demographic as a whole.

Daymond set out to create the company for that specific purpose and even named it FUBU in order to replicate the success and catchiness of other prominent four-letter brands like Nike and Coke. The brand was a big success in the 1990s and many prominent figures wore their clothing, furthering the brand, and with it Hip Hop’s legitimacy as a culture.

Sadly, the brand started losing steam around the turn of the millennium and lost the cultural standing that it carried for much of the 1990s. However, despite this, the company still exists, is still owned by Daymond, and continues to churn out products, and its legacy has long been secured for being the first push in Hip-Hop, and black culture’s eventual push to becoming the dominating culture in the United States that it is today. 

Bucket hats are a style of hat that has a downward-sloping brim around the cap. It too started out as outdoor wear but soon evolved.

However, unlike the previous entries on the list, the bucket hat had already become a high fashion trend before hip-hop even got a hand on it. The hat had become a part of high fashion in the 1960s and has ebbed and flowed from fashionable to not since then. 

When it comes to Hip-Hop, one man can be credited with the bucket Hat’s prominence in the genre and the culture, and that man is LL Cool J. The rapper and actor, seen by many as one of, if not the first superstar in the genre, made the bucket hat a premiere part of his ensemble all throughout his most popular period, the late 80s.

Through LL Cool J’s fame and influence, many prominent Hip Hop acts and rappers started wearing it in their own fashion, and it took the decade by storm. The popular brand, Kangol, can be said to have had a hand in the bucket hat becoming as big as they were in the 90s because they promoted it side by side with their own Kangol caps, making it high fashion once again.

Though Kangol, like FUBU, has fallen from mainstream relevance, the bucket hat remains, and it continues to be favored by rappers and hip-hop culture to this day. Many prominent rappers of the modern era have made the bucket hat a signature part of their clothing, with the biggest example being the West Coast rapper, Schoolboy Q who is as synonymous with the bucket hat for modern listeners as LL Cool J was back in his heydey.

Kangol is a British clothing company that is most known for its headwear and iconic kangaroo logo. It was an integral part of 90s hip-hop fashion.

Like with the bucket hat, the Kangol caps were popularized by LL Cool J as the bucket hats he wore were almost exclusively from Kangol. However, as the decade wore on, the company started pushing for different types of the headwear that were all equally popular.

Though more shortlived than the bucket hats, the Kangol caps had a more immediate impact on 90s hip-hop fashion and popular culture as a whole due to their placement in music and movies of the era. Two people, both actors, would make the hat an iconic part of their onscreen clothing ensemble, thus pushing the brand to the forefront of the public consciousness.

These two people were, of course, actors Wesley Snipes and Samuel L. Jackson. The former did so in one of the era’s most popular and culturally important films, New Jack City, where Snipes played Nino Brown, a drug lord, and featured Brown and his crew prominently wearing Kangol caps throughout the movie, with the logo proudly displayed.

Jackson also wore the brand, and not just in one movie but many movies, and that too in popular director Quentin Tarantino’s two hit movies, Pulp Fiction, and Jackie Brown. The actor’s trademark back-turned Kangol hat has become so central to his identity, and the brand itself, that many people equate him with the brand to this day.

Air Jordans are sneakers that Nike made by partnering with popular basketball player, Michael Jordan. They first appeared in 1984.

Prior to the Jordans dropping, sneakers were seen as nothing more than sportswear, especially used by athletes for the express purpose of playing sports only. This is a far cry from what sneakers mean now that sneaker culture has even become a high fashion trend.

The main reason why this change occurred can be directly linked back to the Jordans dropping, and Michael Jordan and Nike’s collaboration has since become a crucial part of not only hip-hop fashion but the impetus point of sneaker culture in general. Though sneaker culture has surpassed Hip-Hop to become a set trend and culture all its own, the impact of Hip-Hop on it cannot be denied.

One of the main reasons why the Air Jordans took off as they did in the 90s is due in part because of Michael Jordan’s growing prominence and relevancy in the decade. Though a giant in basketball, many thought his days putting numbers on the board, but the player saw a momentous return to the sport in the decade, and his deal with Nike showcased that Jordan had not only surpassed basketball but had also become a cultural icon in general.

Despite starting in the 1990s and seeing growing relevancy each year as the decade went by, the Jordans still is one of, if not the most important and desired sneakers in Hip-Hop and beyond. They are not only still in fashion but have become Nike’s premier product to this day with countless rappers, artists, actors, and influencers sporting them, making them perennially fashionable. 

Oversized clothing was a big 90s hip-hop fashion outfit that saw many prominent figures wear them. In fact, of all the trends on this list, this one is the most tied to Hip-Hop.

For a large part of Hip-Hop’s existence both during the 1990s and especially for a big part of the 2000s, Hip-Hop as a genre, and especially its fashion, was intrinsically tied to oversized clothing. It got to a point that large shirts and sagging jeans or pants became synonymous with Hip-Hop.

The person who can be credited for bringing oversized clothing into fashion is the aptly named American fashion designer, Dapper Dan. This Harlem-born immortal figure in Hip-Hop fashion had been styling artists from the mid-80s and was responsible for styling prominent rappers like Rakim, KRS-One, Big Daddy Kane, and especially LL Cool J.

Through his influence, wearing oversized clothing became a fashion statement, and many rappers followed suit, with it first appearing at the American Music Awards in 1994. Since then, rappers both male and female carried the style forward throughout the 1990s mixing oversized clothing with other styles of clothing already on this list like sports jerseys and denim dungarees.

It wouldn’t be until rappers and producers like Kanye West and Pharrell would push back against oversized clothing in the late 2000s that the trend would go out of style. In fact, much of the skinny clothes and off-kilter style that is seen in Hip-Hop today is a direct over-correction of the influence that oversized clothing has on the genre, and for many, is still deeply tied to the genre as a whole.

Flannel is a type of woven fabric that is made of various fineness, especially from wool or yarn. It is perhaps the most 90s fashion trend on this list.

Of all the articles of clothing or brands on this list, flannel is the one item that can be said to be integral not only to Hip-Hop fashion but to 90s fashion as a whole. Also, it is the one trend that was started and popularized by another genre altogether.

The genre that can be credited with popularizing flannel is the alternative rock subgenre Grunge. Grunge rose in popularity alongside Hip-Hop in the 90s, and though it was vastly more shortlived than rap, it spawned some of the biggest and most popular figures in 90s popular culture, namely in the form of band frontmen Kurt Cobain, of Nirvana, and Eddie Vedder, of Pearl Jam.

Flannel was worn not only by these leading men but the band in general, as like many rappers, they too came from lower-income households, but through their success and good looks, made flannel a fashion statement. Given how big of a cultural icon both these figures, and especially Kurt Cobain have since become, it comes as no surprise that Hip-Hop took to flannel as well.

As they were versatile, and most importantly, affordable, many rappers frequently sported flannel, and as they grew in fame alongside Grunge singers, turned the humble clothing into a fashion statement. One can see many prominent rappers of the day wear flannel not only in red carpet events but in their music videos, thus increasing their influence.

Bandanas are a square cloth that is similar to a handkerchief but worn on the neck, face, or head. It has long been a part of many cultures’ clothing.

However, what made them important to 90s hip-hop fashion can be directly tied down to gang culture that was and remains a big part of Hip Hop and rap to this day. Many gangsters wore bandanas to showcase what gang they belonged to.

These gangs can be broadly categorized into two different categories known as the bloods and the crips, with each having many different subsets that are separated by region. The bloods wear the color red in their clothing to symbolize them, while the crips wear blue in their clothing to symbolize them, and these two colors also showcase their separation and distinct rivalry.

Given that many rappers who rose to prominence in the 90s were themselves either in gangs, had family members who were in gangs, or were gang affiliated to some degree, many wore those colors to represent what side they fell in. The bandana rose in prominence as an easy way to let people know what gang or set you were a part of, and as such became a fashion accessory in the process.

Perhaps the biggest adopter and pioneer of using bandanas as a fashion statement and gang signifier is the late Tupac, one of the most beloved figures in both 90s hip-hop and hip-hop in general. Though not a gangbanger, as someone who was affiliated with the Mob Piru Bloods, Tupac wore a red bandana to let people know of his affiliations and to represent the group in both his music and his persona.