35+ Pics From “TRL” That Are So Painfully 2000s & Also Made Us Laugh Because We Don’t Know What Anyone Was Thinking

Jake Gyllenhaal has long had a reputation as a favorite in Hollywood. Like many stars, it often seems like he’s bound to dress well. During his appearance on MTV’s TRL, Gyllenhaal went with a look that was hard to forget.

There’s a lot to unpack here, most noticeably the slanted Dodgers hat. As if that wasn’t enough, we have to wonder why he bothered to double up on his t-shirts even though they’re practically the same size.

We have to say, this look from Jessica Simpson could be a lot worse. Still, it’s pretty quintessentially a staple from the early 2000s. There’s not a part of this outfit that wasn’t individually in style at the time.

Thigh-high boots? Check. Low-rise jeans? Check. Brightly-toned, cropped jacket? Check. Especially finishing off with this chunky headband, Simpson was ready to take on her 2003 appearance on the show.

More than just a model herself, Banks even has her own show to discover new models. The supermodel isn’t immune to a bad outfit now and again, though.

Once again, though, this outfit really does scream “early 2000s.” The concept that doesn’t really fit here is the vest paired with the sundress and a necklace that went past the vest itself! We wonder how this outfit would have worked on America’s Next Top Model.

Cropped top layers were really in during the early 2000s. So, it’s no surprise that someone like Jessica Alba jumped onto the trend.

This outfit is far from the worst that graced the TRL stage. However, we’re not so sure that this cropped, lacy blazer would be as popular today. The jeans really round out this look as a staple for anyone’s closet in the early 2000s, complete with a band to tie the blazer closed.

Hairstyles come in and out of style so fast that it can feel hard to keep up. Bangs have long been a point of controversy and tend to swing in and out of fashion. In the early 2000s, bangs were a safe choice.

In fact, Fergie was even rocking them during her TRL appearance. As if the look wasn’t iconic enough for the time period, she even took the time to curl her bangs in! Of course, it’s all tied together with a cropped coat and tied-off t-shirt too.

Ashlee Simpson was on TRL shortly after the release of her song, “Pieces of Me” and she showed up in an outfit steeped in early 2000s fashion.

First, she has all the staples here. This includes a pair of low-rise jeans, a chunky belt, a jacket worthy of a tracksuit, and plenty of bracelets to accessorize. However, we’re particularly distracted by the jacket. How and why is it only zipped like this?

Denim was everywhere in the early 2000s. It never really went out of style but the era had a particular love for the material. For the most part, the world was focused on low-rise jeans.

However, that doesn’t mean baggy jeans were left out of style. Both Kate Beckinsale and Underworld co-star Scott Speedman are both rocking jeans here but Beckinsale’s baggy, zippered cut for her denim apparel is what really steals the show.

We’ve already covered a few staples from the early 2000s. This includes a love for a cropped cardigan or jacket with just about any outfit. Who says that it necessarily needs to be an outer layer, though?

Why not just go ahead and make the cardigan the star of the show? That’s what Alicia Keys did when she played on TRL in this cardigan-crop top combination. Of course, she couldn’t forget the low-rise jeans and belt either.

The early 2000s were all about layers. Naturally, this led to some interesting combinations as stars and stylists kept trying new things. The idea of a long skirt with a jacket and shirt is really cute, in theory.

However, the exact skirt here definitely steals the show from the rest of the outfit. The layered ruffles and varied patterns definitely demonstrate a taste in bold fashion that most people associate with Raven-Symoné and her beloved character on That’s So Raven.

When it’s hot out, you probably don’t want to throw on a pair of jeans. Still, maybe it’s not the right temperature to comfortably wear shorts yet, either.

In this case, the fashion of the early 2000s definitely has you covered. That’s where a pair of capris would come in handy. They weren’t just for casual wear either. Even Mandy Moore wore a pair of salmon capris when she appeared on MTV’s TRL.

If there was one media icon that many people couldn’t tear their attention away from in the early 2000s was Paris Hilton. When the heiress appeared on MTV’s TRL, she was sure to incorporate some of the most iconic trends of the time.

This included an accessorizing belt, of course, paired with denim. Not to mention, the thick headband and bumped hair were pretty on-trend at the time as well.

Casual style was pretty in during the early 2000s. There were definitely celebrities wearing looks that anyone could try out if they wanted. Eve gave her fans a style to copy when she played on TRL.

The jeans and baby tee were simple, straightforward, and effective. Plus, we have to love her choice of the other extreme when thick belts were usually the accessory of choice. Not to mention, the necklace, belt, and bracelets matching is a nice touch.

The early 2000s saw an increased focus not just on Ozzy Osbourne but on his family as well. That included his daughter, Kelly Osbourne. This pink ensemble was definitely color-coordinated, to say the least.

Did the crowd find it impressive? Unfortunately, it wasn’t quite a hit in that regard. We have to specifically wonder if this outfit might have worked better if the tall, rounded hat just wasn’t a part of it.

Once again, we have to come back to the love for layers early in the decade. It was a trend still running strong when 2006 rolled around.

That’s the year that Ciara made her way to the TRL stage. Not one to miss out on a trend, she was sure to not only add a few layers but a cropped jacket too. We’ll give her points for creativity on the bottom-layer sleeves being longer than the top ones.

There are always a few stars that have a big influence on style. In the early 2000s, Avril Lavigne made herself a bit of an icon. In fact, the star even had her own clothing line starting in 2008.

It was a whole six years earlier than that when she performed on TRL. The t-shirt doesn’t stand out too much but the hot pink pants really do seem quintessential of the pop star’s style.

Sometimes, the simplest things are the right choice. This is particularly true when it came to nailing down a look in the 2000s.

For example, why get complicated when you can just toss on a simple dress and accessorize it with the right belt? If it works for Shakira, it has to be okay, right? In case it wasn’t enough, though, she made sure to throw on plenty of bracelets and boots to fit the style.

Lindsay Lohan made a name for herself as an actress first. That didn’t stop her from trying her hand at life as a musician, however.

That’s why, in 2005, Lohan appeared on TRL, serenading the crowd with “I Want You to Want Me” by Cheap Trick. The blazer sans shirt look that she went with might even pass standards today! The low-rise jeans help keep this anchored in the early 2000s, though.

Before Beyoncé struck out on her solo career, she was a part of Destiny’s Child alongside Kelly Rowland and Michelle Williams. The group appeared on TRL shortly after they won their first Grammy in 2001.

We have to say, they were definitely coordinated during their appearance. On the other hand, we’re not so sure why they opted for a theme of electric blue outfits that seem to be snatched straight from a Technicolor western.

Typically, when you layer something, you start with the lightest and move from there. For instance, you put on a t-shirt and follow it with a jacket. The layering of the early 2000s didn’t follow many rules, though.

There were a few things that you couldn’t pair together if you just tried hard enough. Even with that in mind, we’re not sure how we feel about the look Elizabeth Banks went for here with this shorts-and-leggings combo.

While outfits were part of early 2000s fashion, the style wasn’t limited to clothes. Just like any other time period, don’t forget other aspects of fashion. Alexa Vega wasn’t going to forget to nail down an iconic early 2000s hairstyle before stepping on stage.

The star hit us with a double-feature of concepts popular at the time including thick side bangs and distinct layering. All in all, she managed to hit all the high points of the time, even if they aren’t as popular today.

If there’s one thing that seemed like a foolproof plan in the early and mid-2000s, it was playing with textures. That’s something Solange didn’t shy away from during her appearance on TRL.

To start, we have to love the layered skirt and it’s only fitting to pair it with a chunky belt given the time period. However, we have to take note of the furry boots that she paired with the whole ensemble.

Finding the right hat for an outfit can seem more difficult than it has to be at first. After all, you have so many options. It seems like the designer of the hat Usher rocked at MTV’s TRL couldn’t quite decide what they were going for.

It’s almost a fedora but what really catches the eye is that the brim doesn’t go all the way around the hat. It’s definitely a look that screams that this photo is from the early 2000s.

By the time he appeared on TRL, he had already made a name for himself with some of his most famous roles.

While he’s best known for his action roles, the actor wasn’t going to throw early 2000s fashion to the wayside for his appearance. While the suede jacket might still work today, the fedora is a look that cements this photo as a staple of early 2000s fashion.

Ryan Reynolds has long enjoyed near-universal popularity. So, it’s not much of a surprise that he made an appearance on TRL earlier in his career.

The star’s style has evolved a lot over the years and his light blue ensemble doesn’t quite look like what he’d wear on the red carpet today. In the early 2000s, we can see why he’d lean for a combo including two of the most popular items at the time — denim and tracksuit-style jackets.

The early 2000s were a busy time for Anne Hathaway. With titles like The Princess Diaries and Ella Enchanted coming out, she had plenty of younger fans. That made her appearance on a show with a younger audience like TRL.

She didn’t disappoint when it came to representing the fashion of the time either. When else would you don a polo shirt that fits like a baby tee? The chunky belt really ties the whole thing together.

To be fair, Kid Rock has never been noted for his interest in keeping up with current fashion trends. Still, this look was particularly interesting.

When he stepped onto the TRL stage, the musician opted for a t-shirt and cargo shorts. However, it’s hard to not look directly at his socks right away. It also seems like the hat isn’t quite as casual as the rest of the look.

We’ve seen enough ruffles and layers to notice something about the early 2000s — there was nothing wrong with a bit of flowing fabric.

Reese Witherspoon doubled down on this trend with a polka-dotted skirt and a flowy blouse. To add to the overall early 2000s feel of this outfit, she topped it off with some large sunglasses that anyone would have loved to wear on the beach or to the pool at the time.

It’s not always easy to pick the best hat to go with an outfit. After all, some work really well and some don’t. Most people probably didn’t give JC Chasez’s hat a thought until trends started to change.

However, by today’s standards, most probably wouldn’t consider it fitting to the rest of the outfit. He also made sure to include a layered trend that would probably hold up today — a collared shirt under a sweater.

We’ve already covered the popularity of capris at the time. Making those capris denim only compounded the trends at the time. However, there’s plenty more that makes this outfit such a staple of the time.

Not one to skip the accessories, Lauren Conrad made sure to add a statement necklace as a focal point and a few chunky bracelets for good measure. To finish it all off, she pulled the front of her hair back — a look many tried.

At first glance, this outfit from Orlando Bloom isn’t too bad. It’s not a bad use of monotones and black is a fairly safe color for it. He did manage to sneak in a few of the trends at the time. For instance, the layered black and white shirts.

What really stands out from this otherwise rather plain outfit is the addition of a large necklace featuring a dollar sign. It was a time of statement necklaces, after all.

When it comes to a show featured on music, you’re bound to see some styles of stars who march to the beat of their own drum.

In the early 2000s, Good Charlotte was pretty popular, so Benji Madden’s appearance on TRL was something fans were excited about. Foregoing the style many other musicians we’ve seen so far go far, Madden deferred to a simple outfit and let his hair serve as the focal point of this outfit.

Back in 2005, the line between formal and casual wear was blurred in some very distinct ways. That’s the year that Charlize Theron went on TRL. All in all, we have to say, this isn’t the worst outfit we’ve seen by far.

Still, it seems specific to the early 2000s to pair some high-cut leather pants with a vest and button-down that would suit a semi-formal setting. Of course, it could only go with a layered haircut to fit the current trends.

Just like many other points in fashion history, brands meant quite a bit in the early 2000s. A few really earned people’s hearts as a trendy choice. This included the iconic Von Dutch merchandise.

For the most part, people opted for hats with the Von Dutch logo. Hilary Duff decided to take things a step further during her TRL appearance. The result was these hot pink, leather Von Dutch pants that no one would forget anytime soon.

As we said, the line between formal wear and casual wear got more than a little blurry during the early 2000s. This led to a few interesting combinations. Britney Spears was one of the biggest icons the world knew during the late ’90s and early 2000s.

Still, we’re not so sure that the cropped button-down could come from any other era in fashion history. Naturally, it could only go with low-rise capris, complete with a thick belt to top the look off.

As we’ve said again and again at this point, layers were the way to go if you wanted to pull off an iconic look in the early 2000s.

That’s exactly what Brandy went for in this skirt and shirt combination, finished off with an accessorizing belt and pair of dark boots. She also forewent the bright tones that often drew attention at the time for a more monotonous, earth-toned outfit.

For the most part, the early 2000s had a preference for low-rise jeans. Still, that didn’t mean you didn’t have options. You could always rock the right pair of high-waisted pants if you wanted.

Ashley Tisdale really committed to the extreme in this pair of pants that reach halfway up the textured pink blouse. Plus, would it even be 2007 if you didn’t pick a few bracelets to stack with the look?

Fashion is a moldable concept and you don’t have to do exactly what everyone else is doing. You can shake it up!

Pink has a lot of the staples of the era here from low-rise pants to a cropped shirt and even a large belt to boot. However, as we would expect from Pink, she has her own twist on the look. A few spray-painted patterns and studs later, you’ve got a much different look.

If you need a dress in the early 2000s, you couldn’t go wrong with a tiered dress. Like we’ve said, layers were the name of the game. As such, Jennifer Lopez was right on trend with this look.

To make sure to add some layers on the top too, a bright cardigan and thick belt were a popular choice. All in all, while it looks a lot different from today’s appearances, J-Lo’s look here was probably a hit on TRL.

Some accessories last throughout the years, even if they’re adapted to fit a modern style. Other accessories just tend to fall out of popularity eventually.

Today, most people don’t bother to accessorize with a wallet chain. On the other hand, in the early 2000s, it was the look to try out. When Nick Carter of the Backstreet Boys appeared on MTV’s TRL, the look was popular enough for him to don.

The good news about the casual trends of the early 2000s was that almost anyone could try them out. Some weren’t relegated to the red carpet.

For instance, you probably saw some friends wearing t-shirts over long-sleeved shirts as you passed them in school. It wasn’t a look sequestered to classtime either. Apparently, it was popular enough that even Colin Farrell repped the look during his appearance on MTV’s TRL.

The right headwear went a long way in the early 2000s. That’s why Vanessa Carlton was sure not to forget this hat for her appearance on TRL. She didn’t stop there in choosing early 2000s trends either.

The denim skirt really ties it together and, of course, you can’t leave home without a statement necklace. We have to say, a deep neckline was an effective way to really let the necklace stand out against the patterned shirt.

A lot of stars who stopped by TRL opted for layers in their look. Rachel Bilson really takes the cake for going all the way, though. There are definitely a lot of layers to this outfit from the shirt and pants under the dress to the cardigan on top.

Not to mention, she didn’t forget to grab an eye-catching belt and a few statement necklaces. It’s a look that definitely caught the crowd’s eye.

There were few people that had as much fame as Christina Aguilera in the early 2000s. So, her appearance on TRL was pretty exciting. She made sure to bring almost every trend of the time with her, too.

The look here includes it all — a bucket hat, low-rise capris, a crop top, and even a scarf to tie it all together. Her thick black highlights in otherwise platinum hair add a distinctly early 2000s flair, too! Of course, she couldn’t forget the pink boots either.

Musician Stacie Orrico played live on TRL UK, rather than the US version. At the time, fans got to see her play her song “Stuck” on the show.

The outfit she chose could only come from the early 2000s, too. The first things that catch your eye about the outfit are, of course, the layered shirt and thick belt. Then, we can’t help but notice the jeans with the top cut off as well.

IF you weren’t interested in a slim-fitting low-rise pair of pants during the early 2000s, you could always opt for the other extreme. That’s what Jewel did when she chose these loose-fitting camo cargo pants.

If that wasn’t eye-catching enough, the musician decided to spice up the plain tank top paired with the pants by literally putting a bow on it. It’s definitely a mix of a few different styles at the time.