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

MTV's Total Request Live was a great way for celebrities to connect with teen viewers. Today, it's a great snapshot of the fashion of the early 2000s. While some of the looks from TRL are definitely iconic to the era, some do leave us wondering what everyone was thinking at the time.

Jake Gyllenhaal

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.

Photo by Lawrence Lucier // Getty Images

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.

Jessica Simpson

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.

Photo by Evan Agostini // Getty Images

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.

Tyra Banks

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.

Photo by Michael Loccisano // Getty Images

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.

Jessica Alba

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

Photo by Michael Loccisano // Getty Images

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.