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

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.

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.

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.

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.

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.

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.

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. 

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.

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.

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? 

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.

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.