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

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Getty Images, Interscope Records

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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2. Trucker Hats

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Getty Images

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

5. Headbands

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

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

10. Durags

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

13. Bandanas

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Getty Images

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

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

17. 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

20. Camouflage

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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