20 TRL Outfits From the 2000s That Will Have You Feeling Nostalgic

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

This wasn't an official TRL appearance, 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

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 baggy jeans and a denim jacket 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

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 Cam’ron was living good. He is rocking a colorblocked Pelle Pelle with the studs, an 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 Motorola flip phone. —Lei Takanashi

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 in the full powder blue set on live television while flexing a baseball shirt your own label, Bloodline Records.—Lei Takanashi

LRG 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 and Co. Five Time Zone watch. —Aria Hughes

Does it get more 2000s than a bleach blonde Eminem flipping double birds beside Carson Daly? Daly had been running the countdown since the show premiered in 1998, and he's been clear about who mattered most to it. On the Emmys red carpet in 2024, Billboard asked him who he'd book first if he got to host an episode today. He said, "I have to say Marshall (Mathers) because Em was there from the beginning." For many, this duo defined an era of music and television.

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

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

Back in 2004, Kanye West wasn’t quite the rap superstar he would become. 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 orange and blue Polo rugby sweater layered over a 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 (worn by Don C) by his side make this photo an even more amazing dose of Aughts nostalgia.—Michael DeStefano

Getting your own TRL special was the clearest sign the show had handed you the keys, and in 2002 Aguilera got one. The program, built around her Stripped era and hosted with Carson Daly, turned an afternoon countdown show into a full New York City showcase for a single artist. For the momentous occasion, the pop star wore an ensemble incredibly indicative of the trends at the time, but looks more like a hodge-podge of random items through a modern lens.

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

You can’t talk about TRL without mentioning N'SYNC. The iconic boy band drew crowds of tens of thousands whenever it stopped by TRL’s Times Square studio. The group was so big at one point that TRL even dedicated entire weeks of programming to them. Here, we get a little bit of everything: denim jackets, frosted tips, turtlenecks, bandanas, futuristic sunglasses, and cargo pants. It’s like an index of 2000s fashion. Which member’s fit was the best of the bunch?

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

LeBron James has been an NBA superstar since the day he got drafted. He was already making appearances on major television programs in his rookie season. If you were unsure about how long ago this was, just look at the size of his Barry Sanders throwback.

Of course, one of the biggest rappers of the 2000s has pulled up to the TRL studio. 50’s pinwheel fitted is very fitting for the era, but the best accessory of the fit is his legendary G-Unit spinner pendant.

This is an incredible relic of a simpler time for a number of reasons. First off, a Tony Hawk and Busta Rhymes linkup is just amazing. Secondly, that neck brace that Hawk is wearing is actually a piece of promo merch for Busta’s single “Break Ya Neck.” We just aren’t doing shit like this anymore.

By 2001 standards, the legendary trio was killing it. There’s no greater relic of 2000s pop culture present than Beyonce’s “Bootylicious” belt chain.

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 Garçons PLAY red heart logo stitched on the chest. —Mike DeStefano

Teyana Taylor came through TRL back in ‘08 wearing a Billionaire Boys Club hoodie under a silver moto jacket that she paired with raw denim jeans and some grey Jordans. At the time, BBC ICECREAM was Taylor’s brand of choice. It’s crazy to see how much her style has evolved over the past 18 years, but this look is timeless.