The early 2000s were a fruitful time for fashion and streetwear. Brands like BAPE, LRG, and BBC were becoming household names, and part of that was due to celebrities like Lil Wayne, Pharrell, and Kanye West donning these brands on MTV's TRL, the video countdown show that aired from 1998 to 2008—MTV recently tried to bring it back. 

Visiting MTV's Times Square studio in New York City became a rite of passage for artists wanting to promote their new albums, movies, or singles. And most guests came dressed in their finest. Ahead of the Nelly and Ludacris Verzuz battle, which takes place on May 16 at 7 pm EST, we thought it made sense to look back on the fashion that dominated this time period. Here are the best style moments from TRL. 

Aaliyah Promoting 'Romeo Must Die' in 2000

To promote “Romeo Must Die,” the film she starred in alongside DMX and Jet Li, Aaliyah appeared on TRL wearing a denim jumpsuit from Roberto Cavalli’s Spring/Summer 2000 collection. She accessorized with a gold body chain, a pair of Timberlands and oval shaped sunglasses. This was a stage when Aaliyah started to work with stylist Derek Lee and was elevating her tomboy style with luxury brands. —Aria Hughes

Nelly Performing at MTV's 'TRL' Tours Southern California in 2001

This wasn't an official TRL apperance, but this outfit probably best represents Nelly's contributions to the 2000s style canon. To perform at MTV's "TRL" Tour in Southern California, Nelly wore a custom basketball jersey and short set, a durag accessorized with a sweatband, and his signature under-eye bandaid. This was shortly after he released "Country Grammar," which would go on to be a multi-platinum album. —Aria Hughes

Jay-Z and Beyonce Promoting ‘03 Bonnie and Clyde’ in 2002

During TRL’s "Spankin' New Music Week," Jay-Z and Beyonce arrived outside of the Times Square studio driving a red 1957 C1 Corvette. Jay-Z wore a baggy jeans and a denim jacket he wore over a grey hoodie, while Beyonce wore a strapless denim dress with the Manolo Blahnik Timberlands she helped popularize in the “03 Bonnie and Clyde” video. Denim on denim was a 2000s staple and Beyonce and Jay-Z cemented that with their TRL appearance. —Aria Hughes

Cam'ron Post 'Come Home With Me' Release in February 2003

When Killa Cam came on TRL in February of 2003, he had just made his debut on Roc-A-Fella last year with his third studio album Come Home with Me. That album went Platinum. His singles “Hey Ma” and “Oh Boy” hit top five spots on the Billboard Hot 100, and he was readying for the release of Dipset’s first record, Diplomatic Immunity. This outfit on TRL shows that Camron was living good. Here he is rocking a avant-garde colorblocked Pelle Pelle with the studs, a Arizona, an orange Atlanta Hawks fitted that matches the jacket perfectly, and a cream Coogi sweater to complete the set. He is also holding the infamous Baby Phat Motarola flip phone. —Lei Takanashi

DMX Promoting 'The Grand Champ' in 2003

In September of 2003, DMX released his third studio album, The Grand Champ. And he really meant it with that title because it debuted at No. 1 on the Billboard 200, meaning that DMX had five albums top the Billboard 200 back to back at this point. The best way to flex how many record sales you got? Dressing up like a Columbia 11 on live television while flexing a baseball shirt from his label Bloodline Record.—Lei Takanashi

B2K in December 2003

LRG, a streetwear brand founded by Jonas Bevacqua in 1999, was one of the most prominent clothing brands during the early Aughts. Here we have B2K’s Lil Fizz, who goes by Dreux now, wearing an LRG varsity jacket. Everyone is outfitted in baggy jeans, Air Force 1s, and it looks like Omarion and J-Boog are wearing another staple from the 2000s, the Jacob the Jeweler Five Time Zone watch.—Aria Hughes

Ludacris Rocking Pelle Pelle March 2004

At this moment, Ludacris was riding off the success of his fourth studio album, Chicken and Beer, and was thankfully not in that movie Crash just yet. Here he’s seen rocking a leather Pelle in a mocha colorway with a Piet Mondrian-esque pattern. God bless you, Luda. —Lei Takanashi

OutKast in 2004

For the 2nd Annual MTV "TRL" Awards, Big Boi and Andre 3000 of Outkast stopped by TRL to perform “Roses,” wearing their Sunday’s best. Big Boi donned a green blazer and pink shirt, while Andre 3000 wore a madras print Ralph Lauren Polo shirt and cuffed wide-leg jeans. It’s the ideal mix of preppy and Atlanta. —Aria Hughes

Fonzworth Bentley Performs with Outkast in 2004

We have to shout out Fonzworth Bentley, who was the mascot for dapper style during the Aughts. He performed “Roses” with Outkast, but before that he walked the step-and-repeat wearing a suede jacket, argyle sweater, corduroy trousers, and a polka-dot bow tie. And of course, he had his signature umbrella in hand.—Aria Hughes

Kanye West Promoting 'College Dropout' in 2004

Back in 2004, Kanye West wasn’t quite the rap superstar he would become. The College Dropout was his first time stepping away from the production side and in front of the mic for his own major album. To mark the occasion, he stopped by TRL in a colorful striped rugby sweater, green button-up, and a Gucci backpack—an unconventional signature look that he would help popularize at the time. The Roc-A-Fella chain around his neck and Drop-Out bear mascot by his side make this photo an even more amazing dose of Aughts nostalgia.—Michael DeStefano

Vote or Die Diddy in 2004

One of the most memorable moments of P. Diddy’s career in the early 2000s was his "Vote or Die" campaign. During a heated election year that ended up with John Kerry going against George W. Bush, Diddy decided to launch a non-partisan campaign that aimed to send younger voters to the polls. Although some felt that Diddy’s blunt message and media onslaught didn’t actually translate into more youth voting, it’s a message that still holds value today. —Lei Takanashi

Jay-Z in 2004

Before his signature “All Black Everything” attire a few years down the line, we were blessed with Jay-Z’s preppy “retirement” fits. Hov stopped by the Times Square studio in November 2004 elevating the striped button-up and jeans look he helped popularize at the time by layering it with a black cable knit sweater. Crispy Evisu denim, his Reebok S. Carter sneakers, and a Yankees fitted (of course), Jay-Z had everyone trying to pull of this style back in the day. —Mike DeStefano

Pharrell in 2005

If Pharrell wasn’t wearing his own brands in 2005, chances are you saw him repping his close friend and streetwear legend Nigo. Here is a perfect example that sees Skateboard P in a Billionaire Boys Club T-shirt, one of Bape’s colorful camouflage hoodies that became indicative of the era in fashion, and a matching pair of Bape Roadstas. People still dress like this today. Pharrell’s style impact is evident.—Mike DeStefano

Pharrell Performed 'Can I Have it Like That' in 2005

Pharrell pulled up to TRL’s Spankin’ New Music Week in 2005 to perform his single “Can I Have it Like That” in signature Aughts swag. The BBC ICECREAM “Diamond and Dollars” all-over print hoodie, “Cone and Bones” ICECREAM logo T-shirt, Louis Vuitton rainbow monogram bandana, and slightly crooked fitted cap literally defined an era of streetwear. His glistening N.E.R.D. pendant designed by Jacob the Jeweler is the perfect finishing touch. Like he raps in the song, his name is Skate-Board-P. —Mike DeStefano

Kanye West Attends 'Spankin’ New Music Week' in 2005

You see this coat?! While this fit came a full decade before Kanye West’s legendary airport one-liner, it is obvious the man has always appreciated a fine piece of outerwear. He kept the rest of the outfit simple with a white V-neck T-shirt, baggy denim, and some white Vans slip-ons.—Mike DeStefano

Lil Wayne in January 2006

A few weeks after releasing his highly-regarded project, The Carter II, and inaugural installment of his legendary The Dedication mixtape series, Lil Wayne hit the TRL studio in this era-defining look. The BBC ICECREAM T-shirts, camouflage cargo pants, and Boston Red Sox fitted cap were all in regular rotation for Weezy F. Baby at the time. A year later, MTV crowned him the Hottest MC in the Game. This is a look at Wayne right as he before his monumental run that followed over the next few years. —Mike DeStefano

Kanye West Attending TRL’s Special VMA Nominee Announcement Show in 2007

The shutter shades. Another fashion trend birthed by Kanye West during the Graduation era. Even though these things are boardwalk T-shirt shop fodder nowadays, Kanye had everyone wearing this highly impractical eyewear back then. Here he pairs a white pair of the plastic frames with a bright yellow Fendi T-shirt, leather jacket, and some lightly distressed denim. He ended up performing on this particular episode as well. —Mike DeStefano

G-Unit Promoting 'Terminate on Sight' in 2008

When G-Unit pulled up rocking colorful Pelle Pelle jackets in three different flavors, they had just dropped their second album, Terminate on Sight. Their appearance on TRL came shortly after Young Buck was axed from the group. —Lei Takanashi

Fat Joe Showing Support for Barack Obama in 2008

Here Fat Joe gave Barack Obama the official Terror Squad cosign, rocking all blue for the Democrats and flexing a pair of custom Obama Air Force 1’s. Of course, this cosign was monumental to getting Obama on the real Air Force One. —Lei Takanashi

Kanye West Promoting 'Impossible' Single in 2006

One time in 2006, Kanye West came on TRL to promote a single that has been long forgotten about since it never appeared on any of West’s studio albums. “Impossible” was a song featuring Twista, Keyshia Cole, and BJ. It was exclusively made for the Mission Impossible III soundtrack. Although this rhinestone BAPE and Murakami x Louis Vuitton fit is still hitting today, that song is best left in the past. —Lei Takanashi

Drake Promoting ‘Degrassi High’ in 2007

It’s funny to think about now, but back in 2007 Drake wasn’t quite a multi-platinum rap superstar just yet. On this particular afternoon in October of that year, he pulled up to TRL’s Times Square studio as “Aubrey Graham, star of Degrassi High.” Before Virgil Abloh had the Patek on his wrist going nuts, Drake was opting for much tamer fashion choices. This black cardigan/white T-shirt combo, fresh fade, and baggy grey jeans was a perfect ensemble for Wheelchair Jimmy that made sense for a star of a teen drama series to be rocking. In fact, this look remained a Drake signature back in his So Far Gone era too, elevated ever so slightly with a Comme des Garcons PLAY red heart logo stitched on the chest. —Mike DeStefano

Teyana Taylor in November 2008

Teyana Taylor came through TRL wearing a Billionaire Boys Club hoodie under a silver moto jacket that she paired with baggy jeans and cool grey retro Jordan 3s. Teyana Taylor, who was signed to Pharrell's Star Trak record label at one point, has always been the poster child for sneakers and streetwear, and we saw a first glimpse of that with this appearance.—Aria Hughes

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