90s HIP HOP FASHION

The 1990s, often celebrated as the golden era of Hip Hop music, also established lasting precedents in fashion that continue to shape our style today. The impact of 90s Hip Hop fashion is still evident, which is why we’re exploring the most iconic trends and brands from that era to inspire your outfit choices.

Our admiration for the 90s era has expressed itself in various ways, from fashion brands incorporating its aesthetic into their collections to musicians featuring these styles in their music videos. Moreover, today’s youth are reviving many of the iconic trends from that time. Let’s dive deeper into how these influences are reshaping contemporary fashion and culture.

Bandana Clothing

The bandana stands out as another geographical fashion item, closely associated with West Coast rappers and gang culture. In the 90s, it became a symbol of identity and affiliation, particularly among artists hailing from Los Angeles.

Rappers often wore bandanas to represent their respective neighborhoods, with the vibrant colors signifying different gang affiliations—red for the Bloods and blue for the Crips. This visual representation of loyalty and belonging naturally transitioned into the music of the era, influencing the overall aesthetic of West Coast Hip Hop.

As artists incorporated the bandana into their fashion choices, it became not only a cultural marker but also a prominent accessory in music videos and performances, further solidifying its place in Hip Hop fashion history. The bandana’s enduring presence in contemporary styles reflects its deep-rooted connection to the culture and its evolution over time.

At the forefront of 90s Hip Hop fashion is the iconic suede boot, a style steeped in heritage and deeply connected to the culture.

The boot’s origins date back to the 90s, with nearly every prominent East Coast rap artist, from Jay-Z to Biggie Smalls and Mobb Deep, donning this footwear. Originally designed for construction workers, the boot gained traction among New York drug dealers, who favored it for its durability in harsh weather conditions. As many drug dealers and hip hop artists hailed from the same neighborhoods, upcoming rappers were naturally influenced by this rugged aesthetic, solidifying the suede boot’s place in hip hop culture.

American Sportswear Brands

In the 90s, Hip Hop quickly forged a connection with American sportswear brands like Tommy Hilfiger and Polo Ralph Lauren, as artists sought more sophisticated silhouettes beyond traditional designer labels.

A pivotal moment occurred in 1994 when Snoop Dogg performed on Saturday Night Live wearing a Tommy Hilfiger polo shirt that had been gifted to him just hours before the show. This appearance not only showcased the seamless blend of Hip Hop and sportswear but also encouraged many Hip Hop and R&B artists to infuse their personal styles with these brands.

Aaliyah exemplified this trend perfectly; she appeared in numerous campaigns for Tommy Hilfiger while embodying 90s Hip Hop fashion through her signature looks of baggy jeans and crop tops. Her style captured the essence of the era, blending comfort with a chic aesthetic that continues to inspire today.

Puffy Jacket

While the plaid jacket is emblematic of West Coast Hip Hop fashion, the puffy jacket holds a similar significance for East Coast Hip Hop.

The puffy coat, much like the Timberland boot, was adopted by East Coast MCs as a practical response to the harsh winter weather. Its oversized, insulated design became a staple among Hip Hop artists and Black youth in the neighborhoods, representing both functionality and style.

Typically paired with New York Yankees caps, hoodies, and boots, the puffy jacket became a key element of the East Coast aesthetic, capturing the grit and resilience of urban life. This distinctive look has even inspired a host of memes over the years, highlighting the unique blend of practicality and cultural expression that characterizes New York’s Hip Hop fashion scene.

Snap Back Caps

The snapback cap is an iconic symbol of 90s Hip Hop fashion, and its association is well-founded. Take The Fresh Prince of Bel-Air, for instance; the show featured a young Will Smith who frequently donned snapback hats throughout multiple episodes, showcasing the trend’s prevalence during that time.

While the early 2000s saw the 59FIFTY fitted cap rise to prominence as the preferred choice, the snapback experienced a revival over the past decade, notably fueled by tracks like Tyga’s “Snapbacks Back.” This resurgence serves as a clear indication that the influence of the 90s remains strong, with many still rocking snapbacks today. The enduring popularity of this style underscores its lasting impact on hip hop culture and fashion.

Pelle Pelle

Pelle Pelle skyrocketed to popularity in the 90s for two key reasons. First, the leather outerwear company became a favorite among East Coast rappers who embraced its bold and stylish pieces as a key part of their wardrobe.

Second, Pelle Pelle was one of the first brands to introduce the designer baggy pants look, which resonated with the urban market. Recognizing a demand for leather jackets tailored to the streetwear aesthetic, they seized the opportunity to create fashionable outerwear that would redefine urban style.

In the 90s, it was nearly impossible to watch a music video from East Coast artists like Keith Murray, Guru, and Nas without spotting one of their signature leather jackets. Pelle Pelle’s influence during this era helped to solidify its status as a cornerstone of Hip Hop fashion, leaving a lasting impact on the culture.

Graffiti Clothing

In the early days of Hip Hop, graffiti emerged as a powerful form of self-expression for individuals in New York’s low-income neighborhoods. As one of the four main elements of Hip Hop culture, graffiti found its way from the streets, subways, and trains into the realm of fashion.

The vibrant colors, striking graphics, and bold patterns characteristic of graffiti solidified its significance in Hip Hop culture. Pioneering brands like Shirt Kings utilized their graffiti artistry to create airbrushed designs on apparel worn by icons such as LL Cool J, Big Daddy Kane, and Mike Tyson. This fusion of art and fashion not only showcased the creativity of the culture but also helped to popularize graffiti as an essential element of Hip Hop style.

Bucket Hat/Kangol Caps

Kangol caps owe much of their popularity to LL Cool J, who sported them in numerous music videos during the 80s and 90s. This iconic headwear also received notable product placement in the film New Jack City, where Wesley Snipes and his crew showcased the hat throughout the movie.

In addition to Kangol caps, hip hop fans looking for more affordable options often turned to regular branded bucket hats in the 90s, influenced by the Kangol style. While Kangol caps may not be as prevalent today, the bucket hat has remained a contemporary favorite, with its roots tracing back to the vibrant fashion of the 80s and 90s. This enduring accessory reflects the lasting impact of that era on modern fashion trends.

Bomber Jacket

Certain fashion pieces are deeply connected to specific subcultural movements, with each garment symbolizing the identity and values of its respective community. For example, denim jackets are synonymous with punk, parkas with the grunge movement, work shirts with skateboarding culture, and bomber jackets with Hip Hop.

The bomber jacket, in particular, gained massive popularity within the Hip Hop scene as the culture began to intertwine with sports, as previously discussed in the jersey section. The 80s baseball bomber style became a staple in the 90s, largely influenced by iconic acts like RUN DMC.

These jackets were not just functional; they represented a fusion of style and identity, showcasing the artists’ connection to sports culture while simultaneously making a bold fashion statement. The bomber jacket’s versatility and strong cultural ties have allowed it to remain a significant piece in both Hip Hop fashion and broader streetwear trends today.

Double Denim

In the 90s, urban brands like Karl Kani, Rocawear, Ecko Unltd, and Johnny Blaze recognized the evolution of denim from workwear to a fashionable staple. They embraced this shift by introducing baggy and oversized denim pants and jackets that resonated with the Hip Hop aesthetic.

While subcultures such as punk rock had incorporated denim into their styles in the 80s, Hip Hop began to adopt and adapt denim around the same time RUN DMC brought streetwear into the mainstream. This trend allowed young people in urban areas to express themselves through fashion.

Often styled with Timberland or Lug boots, the denim look of the 90s emerged as an accessible and affordable fashion choice for Black youth in inner cities. It not only reflected the culture’s creativity but also helped to solidify denim as a key element of Hip Hop fashion, making a lasting impact that continues to influence streetwear today.

Oversized Clothing

A significant aspect of 90s Hip Hop fashion was the embrace of oversized clothing, with artists often donning pieces that were two sizes too big—a trend that has made a notable comeback today.

This culturally rooted style, commonly referred to as urban fashion, gave rise to iconic brands like Fubu, Phat Farm, and Wu Wear, all catering to a demographic that shared a love for this aesthetic. While contemporary Hip Hop artists frequently sport designer and luxury brands, the 90s celebrated a bolder, more confident expression, encapsulated through the oversized silhouettes that defined the era. This trend not only represented a unique fashion statement but also a cultural identity that resonated deeply within the Hip Hop community.

Plaid Jacket and Shirts

Flannel shirts and plaid jackets became staple pieces for West Coast Hip Hop artists, gaining popularity through figures like Snoop Dogg and films such as Menace II Society and Juice. This distinctive style not only defined the aesthetic of the West Coast Hip Hop scene but also resonated with broader cultural trends, reflecting the laid-back yet bold attitude of the era.

Today, flannel and plaid remain prominent in fashion, transcending their original context while still carrying echoes of their 90s roots. The continued relevance of these styles underscores their influence and enduring appeal within Hip Hop culture and beyond.

Adidas Superstars

RUN DMC pioneered the first partnership between a sportswear company and a music group, establishing themselves as cultural icons in the realm of streetwear and Hip Hop fashion.

In the early days of Hip Hop, artists like Melle Mel and Afrika Bambaataa drew inspiration from African King attire and Glam Rock styles. However, RUN DMC introduced a more street-authentic aesthetic that significantly transformed Hip Hop fashion. Their unique style would go on to influence millions around the globe, shaping the trajectory of fashion within the genre for years to come.

With the success of their hit song “My Adidas,” RUN DMC became representatives of black urban youth across America, embodying a style that seamlessly transitioned into the 90s. This era of Hip Hop fashion featured signature looks that included tracksuits from head to toe, bucket hats, and rope chains.

The partnership with Adidas not only laid the groundwork for how artists dressed throughout the 90s but also opened the door for more collaborations with other artists, such as Kanye West with Yeezy sneakers, Snoop Dogg, Ciara, and Pharrell. This lasting influence demonstrates how RUN DMC’s legacy in fashion continues to resonate within the industry today.

MLB and NBA jerseys

Sports jerseys have long been a staple in Hip Hop culture, frequently appearing in music videos where artists proudly represent their home teams. Over the years, the relationship between sports, athletes, and hip hop has become increasingly intertwined, as seen in iconic rap videos like Jay-Z and Jermaine Dupri’s “Money Ain’t a Thang” and Will Smith’s “Summertime.”

Both of these tracks, released in the 90s, highlight how artists wore their jerseys as bold fashion statements. The jerseys not only served as a way to show team pride but also became emblematic of the artists’ personal style and cultural identity, further solidifying the connection between hip hop and the world of sports.

Military Clothing

As Hip Hop emerged as a powerful voice in America, artists and groups like Tupac Shakur, Public Enemy, and Nas used their platforms to address pressing political issues affecting Black Americans.

Whether consciously or not, military gear served as a uniform that reinforced the messages conveyed in their lyrics, symbolizing the struggle against systemic oppression faced by Black communities. While military clothing became a fashion statement in the 90s, it also became the preferred attire for artists aiming to deliver a strong message while maintaining a visually impactful presence. This trend resonated with influential figures like Biggie and Das EFX, who adopted similar styles.

Beyond its political implications, camouflage also gained popularity as a major trend in the 90s, continuing to influence fashion today. The fusion of military aesthetics with Hip Hop culture not only highlighted the genre’s social consciousness but also solidified military wear as an enduring staple in urban fashion.

Dungarees

Dungarees exemplify the experimental spirit of 90s fashion, as they were embraced by artists seeking a cool and comfortable aesthetic. Originally designed as protective work garments, similar to Timberland boots, Hip Hop artists transformed dungarees into a bold fashion statement.

This style gained popularity during the 90s thanks to influential figures like Will Smith, 2Pac, The Fugees, and TLC. Their unique interpretations of dungarees showcased how functional clothing could be reimagined within the realm of Hip Hop, blending comfort with style in a way that resonated with fans and left a lasting mark on fashion trends.

cONCLUSION

In conclusion, the fashion of the 90s Hip Hop era has left an indelible mark on contemporary style, reflecting a rich tapestry of cultural identity and artistic expression. From oversized clothing and iconic footwear like Timberland boots to the symbolic use of accessories like bandanas and bomber jackets, these trends not only defined a generation but also continue to influence modern fashion.

As artists utilized their platforms to showcase their unique styles, brands began to cater to the tastes of a burgeoning urban market, resulting in the rise of iconic labels and a new standard in streetwear. The fusion of Hip Hop with sportswear and the incorporation of bold graphics, denim, and leather created a vibrant aesthetic that resonated with youth culture.

Today, the nostalgia for 90s Hip Hop fashion remains strong, with designers and influencers drawing inspiration from this influential era. As we explore the styles and trends that emerged during this time, it becomes clear that the legacy of 90s Hip Hop fashion is not merely a relic of the past but a continuing source of inspiration that shapes our wardrobes and cultural expressions today.

7 ESSENTIAL STYLE TIPS FOR MEN OVER 50 BEFORE YOU SHOP

Navigating the world of fashion in your 50s (and beyond!) may seem daunting, but trust me, it’s entirely achievable. While I can’t personally guide every man receiving an AARP membership in the mail, I can offer you this comprehensive guide to dressing for mature men.

If you’re new to my writing, you might be asking yourself: Caroline, as a 29-year-old woman who spends her free time watching Nordic crime dramas and perfecting my homemade macaroni and cheese, what do I know about the style dilemmas faced by men approaching early retirement?

Well, for one, I have a soft spot for well-dressed older gentlemen.

Every man over 50 has unique wardrobe needs that reflect his personal style and lifestyle. Whether you’re searching for casual attire, looking for shopping recommendations, or simply wanting to elevate your fashion game, dressing well at this age can be just as exciting and diverse as it is for younger men.

Not sure where to begin? No need to fret! Below, 7 tips on nailing mature style for men:

Get a tailor

Everyone I’ve spoken with in the realm of men’s style, especially for those over 50, agrees on one crucial point: the difference between “a guy wearing clothes” and “a well-dressed man” often comes down to good tailoring.

Building a relationship with a tailor is essential for any mature man looking to elevate his style.

Consider your tailor your clothing’s doctor. Just as you have a dentist for your teeth, an internist for your health, and a dermatologist for those pesky moles, it’s time to have a tailor on speed dial to ensure your wardrobe is in top shape.

Now, I can already hear you thinking: “The clothes I own fit me just fine!”

But let’s be real—no man, and I mean none of you, can wear off-the-rack clothing perfectly.

Sure, you don’t need to have every t-shirt tailored or sweatpants hemmed, but those button-down shirts you wear daily with jeans or chinos? Get the sleeves adjusted to the right length.

And don’t forget about those jeans and chinos! 

What about the blazer you wear for dinner with your spouse each week? Could it use a little adjustment to fit you better?

Think of this process like visiting a doctor. You don’t go in every day for every little issue, but for the significant matters, you want to consult a professional. 

Focus on the finishing touches 

When it comes to presentation, the key differentiator between well-dressed men and those who simply wear clothes is the extra attention to detail. These subtle touches may not be immediately noticeable, but once you see them, they make a significant difference.

This attention to detail extends beyond your clothing to grooming, including a well-maintained beard (and nose hairs!), clean nails and cuticles, and a pleasant scent. Just look at the smart tie and coordinating socks worn by Stanley Tucci—voted the most stylish man of 2023 by Style Girlfriend followers!

Accessories are an excellent way to elevate your style as a man over 50. A beautiful scarf can enhance a simple blue overcoat, while the right shoes can complete your outfit—just as easily as the wrong ones can ruin it.

Investing in accessories is a smart choice for your wardrobe. Timeless pieces, like a classic pair of glasses, will never go out of style, and if you choose quality items built to last, you’ll enjoy them for years to come.

I’d like to highlight timepieces: they’re one of the first things I notice on a man. If you wear a watch, I can’t help but notice which one it is.

Let me be clear: you don’t need to spend a fortune on a watch. However, if you can invest in a quality timepiece, it’s often worth it. Even an affordable tank-style Seiko can make you look polished and distinguished.

Invest in forever pieces

By avoiding fleeting trends, you can invest more wisely in your wardrobe. Why? Because when you focus on timeless pieces, you know you’ll wear them for more than just one season.

Instead of purchasing multiple inexpensive shirts and trousers, consider buying one or two high-quality staple items. Then, invest in having those pieces tailored to fit you perfectly. The final step? Embrace the ease and simplicity of cultivating a signature personal style!

Look for brands that prioritize craftsmanship and quality. 

While you may not have the budget to splurge on every item in your closet, you can be strategic about your spending.

Identify the pieces you wear most frequently. If you rarely wear sweaters but often don blazers—think of a post-presidential Barack Obama—prioritize your budget accordingly to reflect your lifestyle.

Lean into a Monochromatic Color Palette

Monochromatic dressing involves combining pieces from the same color family to create a cohesive and polished look. This style not only elongates your body but also gives you a sleek, modern appearance with minimal effort.

Take, for example, the character Steve Martin, 79, plays on Only Murders in the Building. He often sports monochromatic ensembles, like blue jeans paired with a white shirt and a blue knit sweater or overcoat.

For men over 50, these outfits are not only simple to assemble but also effortlessly elevate your style.

You can approach monochromatic dressing in a few different ways. Our favorite at Team SG is the black and blue route—opting for rich, deep blues like navy—or embracing earth tones, such as pairing tan chinos with a chunky oatmeal rollneck sweater.

Aim for leveling up your personal style instead of chasing trends

Here’s a little secret: I often share this advice with my younger clients, but it’s especially true for older gentlemen—dressing for who you are, rather than trying to keep up with the latest trends, makes all the difference.

By midlife, you’ve witnessed countless trends come and go, which makes it easier to identify which cuts and styles flatter you and which colors and textures enhance your personal aesthetic.

Consider what clothing aligns with your lifestyle and which pieces don’t quite fit who you are. 

Think of this guideline not as a limitation, but as a permission slip to bypass fleeting trends. That’s a true luxury! As men age, they naturally become more distinguished—there’s a reason the term “silver fox” is a compliment.

Allyson B. Fanger, the costume designer for Netflix’s (criminally underrated, in my opinion) *Grace and Frankie*, shared that one of the joys of dressing older characters like Robert and Sol—played by Martin Sheen and Sam Waterston, both in their eighties—is that these men have lived rich lives.

The show features two lawyers who leave their wives for each other after their kids have grown up, and their style is spot on.

Robert and Sol don’t need to evolve further in their fashion choices, which makes dressing them all the more enjoyable for Fanger.

They each have favorite brands, signature color palettes, and distinct approaches to style.

Robert is traditional, favoring button-down shirts and chinos—he’s a Brooks Brothers man through and through.

Sol, on the other hand, embodies the spirit of a hippie, opting for Cubavera camp shirts and comfortable Tommy Bahama linen pants.

These characters exemplify how, regardless of personal taste or style, it’s entirely possible to achieve top-notch personal fashion at any age.

Ultimately, knowing who you are and being confident in that is the cornerstone of any man’s style, and that understanding becomes more profound as you accumulate life experience.

Adopt a wardrobe uniform

Larry David, at 76, is a big advocate for uniform dressing. While many people think of a daily uniform as a traditional suit and tie, David exemplifies how versatile and liberating this approach can be.

He’s a king of casual style—if you’re searching for casual clothing ideas for men over 50, the *Curb Your Enthusiasm* star offers an excellent blueprint.

His go-to wardrobe staples include crewneck sweaters, zip-ups, AG 5-pocket chinos, and soft shoulder blazers. 

If the thought of choosing an outfit every day feels overwhelming, this dressing strategy might be perfect for you. 

Consider building a capsule wardrobe filled with a few pieces you love: your favorite pants, a handful of shirts that make you feel your best, and some knitwear or jackets.

And don’t hesitate to buy items you adore in multiple colors! (This is another trick David uses.)

This way, each morning, you can reach into your closet and confidently know that whatever you pick will likely coordinate beautifully.

Be yourself 

It might sound a bit silly to wrap up a list of style tips with a reminder to just accept yourself, but hear me out. You might think, “My style is just a ripped sports jersey and Crocs,” and to that, I say: maybe it’s time for a change! (Just kidding… or am I?)

What I really mean is don’t overthink dressing for a particular age. These style tips are helpful if you’re unsure where to start or want to elevate your look. But if you already have a signature style or enjoy dressing outside the norm, don’t let the number in front of your age hold you back. Embrace what makes you unique and wear it with confidence!

CONCLUSION

In conclusion, navigating style in your 50s and beyond doesn’t have to be a daunting task. Embrace the principles of good tailoring, invest in timeless pieces, and build a wardrobe that reflects who you are. Remember, personal style is all about confidence and authenticity—wear what makes you feel good, whether it’s a classic blazer or a funky shirt.

Don’t shy away from experimenting with accessories and details that can elevate your look. And most importantly, don’t let age define your fashion choices. Celebrate your individuality and express yourself through your clothing. After all, style is a lifelong journey, and it’s never too late to redefine your aesthetic!