To The Window To The Wall: Revisiting 2000s Hip Hop Style

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It might sound cliche, but you really had to be there. The 2000s were in a time both in hip hop and fashion. When reflecting on the early oughts and 2000s hip hop style (particularly the time period from 2000 to 2005), it often evokes an emotion of both nostalgia and laughter from hip hop lovers with more questions than answers. Questions like “Why Did We Wear That” and “What Were We Thinking” tend to come up, but there’s also a sense of appreciation. Appreciation that we had brands like FUBU, Sean John, Rocawear, and Baby Phat.

Appreciation that we had the Von Dutch era. Appreciation for putting together some of the outfits we did, even if in hindsight it looks a little chaotic. And since many of these trends were heavily worn by hip hop artists in their music videos and performances, and rapped/sung about in their songs, these fashion trends are also a reminder of some great times in music.

Today we are looking at 20 of the best 2000s hip hop style trends and why we loved (and continue to love them). Enjoy this blast from the past below.

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FUBU. For Us, By Us. While the FUBU trend started in the 1990s, it did carry over into the early 2000s. FUBU was worn not just by celebrities, but amongst us common folk as well. At its zenith, the brand was popular enough to have an entire album full of hip hop greats featured on it (The Good Life (FUBU Album)), and is still going strong to this day, recently teaming up with Marvel to release a Black Panther: Wakanda Forever collection.

2. Trucker Hats

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Made popular in part thanks to Pharrell. The artist was hardly ever seen without his trucker hats back in the day, which helped spark the trend of trucker hats amongst the skateboarding community. When it comes to the current success of skating and streetwear, you definitely have to credit Pharrell as being one of the pioneers.

3. Denim

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Getty Images

Why did us millennials wear so much denim? It wasn’t just denim jeans, it was denim jackets, denim hats, denim skirts, denim skirts over top of denim jeans (yes this was a thing). Why did we wear so much denim? Who’s idea was it?

4. Rocawear

For those too young to remember, Jay-Z’s first major business venture outside of music was his streetwear line Rocawear, which was representative of all things “Roc Nation.” There was custom Rocawear shirts, headbands, jackets, etc., and of course, the Roc Chain (which was exclusive to members of the Roc Crew, but still). Rocawear still has a place in the hearts of many as it brings back memories of Jigga’s early 2000s albums.

5. Headbands

Which leads us to our next point, headbands were a very popular trend amongst men in the hip hop community back then, and we have to give the credit to Allen Iverson, who popularized it in the late 1990s, and at times had rappers dressed exactly like him with headbands, basketball jerseys and shorts, and sneakers. Nelly was also an avid headband wearer around that time as well. So was Bow Wow.

6. Grillz

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Speaking of Nelly, “Rob the jewelry store and tell 'em make me a grill.” Not only were grills a staple of mid-2000s hip hop culture, Nelly had one of the most popular songs of the 2000s with his 2006 classic “Grillz.” In addition to Nelly rocking grills, you also had Paul Wall, Slim Thug, Wayne, wearing them too, which gave folks even more of an incentive to go get a customized grill.

7. Oversized T-Shirts

Oversized t-shirts that almost hit your knee caps were most definitely a thing from 2000 to around 2007. If you need examples, think of the videos for “Oh I Think They Like Me” and “Lean Wit, Rock Wit It” by Dem Franchize Boyz.

8. Jersey Dresses

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Getty Images

Ah. The late great jersey dress. Jersey dresses were frequently worn by the ladies in the hip hop community with the two most popular examples being Mya in the video for her 2000 single “Best of Me” with Jay-Z where she wore a vintage Jordan UNC jersey dress, and Mariah Carey’s Jordan Washington Wizards dress. We can all virtually agree that Kobe Bryant’s jersey dress was the best right?

9. Basketball/Football Jerseys

And while basketball and football jerseys have become a part of regular everyday wear amongst sports lovers, you can make the argument that the 2000s made it cool to wear them outside of going to games.

10. Durags

Say what you want, but didn’t really see men rocking durags outside of the house like that until the early 2000s when rappers like Eminem, 50 Cent, etc., started doing so. Which leads us to our next point.

11. Durags Paired With Ballcaps

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Interscope Records

It was also very popular to rock fitted caps over top of durags in the early 2000s, tipping them ever so slightly to the side.

12. Sean John

Diddy putting out his Sean John clothing line was a moment that sparked cultural impact. Sean John was everywhere in the early 2000s, making it one of the most popular Y2K brands. Despite Sean John only putting out men’s clothes, you had women cutting up shirts and turning jeans into capris so that they could get in on the action as well (especially in New York). In 2021, Diddy partnered with Missguided to release a women’s only Sean John line, which was an interesting reverse uno if you ask us. 

13. Bandanas

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What were the early 2000s without bandanas? Whether it was DMX and Ja Rule or Aaliyah and Eve, bandanas were definitely one of the biggest early 2000s trends, and they are low key starting to make a comeback. 

14. Air Force 1s

Air Force 1s were already on the rise around 2001/2002 in the hip hop community, but Nelly definitely took things to the next level with his 2002 hit “Air Force Ones” from his legendary Nellyville album.

15. Timberlands

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Back then you had Jordans, Air Force 1s (and other variations of Nike sneakers), Reeboks, and Timbs (with perhaps some PUMA and New Balance thrown in there). Maybe there’s a few others we are forgetting, but Timbs were everywhere (especially in NYC).

16. Pink

Nobody wore pink like Cam’ron. Nobody. From the pink jackets to the pink sweatbands, Cam’ron was determined to knock the notion that the color pink was “too feminine for men” into outer space, and not only did he do that, but it wasn’t long before the fellas were drawing inspiration themselves. Real men wear pink. Period.

17. Chains

Name/brand chains that were sometimes obnoxiously big were yet another memorable Y2K moment. You had Usher wearing his. The Rocafella crew wearing theirs. Snoop, Dre, and Em, wearing theirs. Bad Boy and G-Unit wearing theirs. At this point it might be better to ask who in the 2000s wasn’t wearing branded chains? 

18. New Era Fitted Caps

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New Era

We’ve already talked about the importance of fitted caps in the 2000s, but we have to make it clear that New Era was the dominant brand, which still remains the case in almost 2023. Most of the time when people are buying a new ball cap, it’s New Era.

19. Baby Phat

It’s hard to describe the chokehold that Baby Phat had amongst the women in the hip hop community in the early and mid-2000s. You had Baby Phat tracksuits. Baby Phat jackets being paired with low-rise jeans. Baby Phat jackets being paired with UGGs. It was one of the biggest and most impactful fashion movements, and we have to shout out Kimora Lee Simons for doing the damn thing.

20. Camouflage

Camo is still very much in style, but it’s hard to top the 2000s when it was just about everywhere. From Destiny’s Child wearing all camo in their video for “Survivor,” to Missy Elliot having her background dancers rock it for her videos and performances, we definitely can’t forget the camo era.

What were your favorite hip hop trends from the 2000s? Be sure to keep up with us for more style and content. 

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