Top 10 90s Hip Hop Fashion & Trends

Remember the days when hip-hop was all about the beat, the lyrics, and the culture? when artists like Tupac and Biggie were dominating the charts? Now, let’s talk about the fashion of 90s hip-hop, a style that was as integral to the scene as the music itself. Explore the fashion trends that not only complemented but also played a key role in shaping the narrative of hip-hop during that iconic era.

We’re going to break down the top 10 hip-hop fashion trends from the 1990s and highlight why each one became iconic. Furthermore, we’ll delve into why the 90s hip-hop scene remains unforgettable and continues to leave a lasting impact on our cultural memory.

1. Bucket Hats

bucket hat
A black bucket hat (source: Instagram)

Anyone who is into rap music can tell that Bucket Hats were one of many fashion trends back in the day. Renowned rappers like Biggie, Ice Cube, and Jay Z have sported the bucket hat. Interestingly, while the trend gained momentum in the 90s, it originally found popularity in the late 80s, with the legendary rapper LL Cool J playing a pivotal role in its widespread adoption.

The bucket hat features a brim that slopes downward and it was and still is considered an iconic fashion trend in the world of hip-hop. Following LL Cool J’s popularization of the bucket hat, numerous other artists adopted the trend, and the rest, as they say, is history.

2. Check Flannel

flannel shirt
Ice Cube wearing flannel shirt in movie “Friday” (Source: Facebook)

Flannel emerged as a key player in the 90s fashion scene, making its mark and naturally becoming a staple in the hip-hop scene. Beyond its influence in hip-hop culture, flannel also found favor in another music genre—Grunge. Grunge, an alternative rock subgenre, witnessed a shared appreciation for flannel. In this way, two seemingly disparate music genres found a common thread in the adoration for this iconic fashion piece.

While flannel was a mainstream fashion choice, there could be an additional reason for its surge in popularity within the rap scene. Given the street power and struggles depicted in the 90s rap scene, the affordability of flannel made it a natural and accessible choice.

3. Timberland Boots

timberland boots
The customary Timberland boot stands at ankle height, boasting a distinctive light brown hue, and is renowned for its durability (Source: Facebook).

While Timberland boots remain popular today, their craze reached unprecedented levels in the 90s hip-hop scene. Every rapper from that era, as exemplified in Tupac‘s diss track ‘Hit Em Up,’ seemed to be donning these iconic boots.

While these boots became a potent fashion symbol for 90s rappers, it’s worth noting that they were initially designed for practical purposes. Originally crafted for workers, the waterproof, 6-inch Nubuck leather boot was engineered to endure harsh weather conditions. Clearly, 90s artists emerged from backgrounds of struggle and street life, enabling them to afford Timberland boots. It didn’t take long for these boots to make a significant impact on the fashion style of 90s hip-hop.

4. Jerseys

Sports and hip-hop have always been linked. Drake and other current artists still rock sports jerseys on stage, but it wasn’t as straightforward in the 90s. Back then, jerseys were more than just a fashion statement; they held a deeper meaning in hip-hop culture.

Tupac and Biggie’s legendary beef is etched in hip-hop history, not only involving their friends but also creating a widespread division between the West and East Coast. Rappers from each coast symbolized their allegiance by donning sports jerseys representing their respective regions, adding a visual element to the deep-seated rivalry.

5. Denim Dungarees

Denim Dungarees
An example of the vintage 90s Denim Dungarees (Source: Twitter)

Call it weird or wonderful, one of the standout and popular fashion choices in the 90s hip-hop scene was denim dungarees. Furthermore, similar to timberland boots, denim dungarees (denim overalls) were actually originally made for workers or laborers because of the product’s durability. And just like timberland boots, denim dungarees also became popular.

Numerous renowned artists such as Tupac, TLC (the group), The Fugees, and Will Smith popularized the trend of denim dungarees, elevating it to mainstream and trending fashion status.

6. Bandana

Much like a handkerchief, a bandana is a square piece of cloth. However, it’s typically worn on the face, neck, or head. The iconic rapper Tupac is often photographed with a bandana adorning his head. As mentioned, the versatility of the bandana allows for various styles of wearing it; some also opted to keep it hanging from their pants pocket.

In the 90s hip-hop scene, bandanas were associated with gang culture. Similar to jerseys, different gangs adopted distinct colors of bandanas. In simple terms, bandanas served as a piece of clothing representing each gang.

7. Air Jordans

Air Jordan
Air Jordan 1 (Source: Facebook)

The sneaker culture has grown immensely, with individuals buying and selling sneakers for hundreds of thousands of dollars. Additionally, there are sneakers in the market whose prices reach into the millions. Before the introduction of Air Jordans, sneakers were primarily seen as athletic footwear worn by athletes. However, the game changed entirely in 1985 when Nike collaborated with the legendary basketball player Michael Jordan and launched Air Jordans.

Upon the launch of Air Jordans, Nike initially aimed to achieve $3 million in sales within the first three years. However, the popularity of the sneakers far surpassed expectations, resulting in impressive earnings of not $3 million, but $126 million within just one year. And naturally, it was a popular choice for hip-hop artists as well.

8. Oversized Clothes

oversized tshirt
Oversized clothes are still a thing in the fashion scene of hip-hop (Source: Facebook)

One thing that takes us back to the 90s is the fashion of oversized or baggy clothes, especially in the hip-hop world. This trend didn’t just stick to the 90s; it also carried into the early 2000s. Furthermore, the fashion of oversized clothes was intricately tied to the 90s and early 2000s hip-hop scene. Delving into its roots, American fashion designer Dapper Dan played a pivotal role in popularizing oversized clothing. He styled hip-hop pioneers such as Rakim, LL Cool J, Big Daddy Kane, and others, contributing significantly to the trend’s prominence.

9. Kangol Caps

Prior to the prominence of the bucket hat, Kangol caps were the reigning fashion trend in the 90s hip-hop scene. Numerous artists, including Rakim, LL Cool J, The Notorious B.I.G, Tupac, and others, were captured in photos sporting Kangol caps. Similar to the bucket hat, it appears that LL Cool J played a role in popularizing Kangol caps. However, their presence in the mainstream began earlier, notably in the 1991 film New Jack City. In the movie, the character Nino Brown, a drug lord, and his associates are depicted wearing Kangol caps, marking an early influence on the cap’s popularity.

However, while Kangol caps also enjoyed popularity in the late 80s and early 90s, they did not endure in the mainstream to the same extent as bucket hats, which continue to be favored by artists to this day.

10. Gold Chains

Whether it was The Notorious B.I.G., Makaveli, or any other rapper from the 90s, they really liked wearing big gold chains around their necks. Even though they had other fancy stuff like Rolex watches and more gold things, nothing quite made a statement like those oversized gold chains.

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