Let's Celebrate the 20th Birthday of Britney Spears and Justin Timberlake's Iconic Denim Look

Britney Spears and Justin Timberlake rocked their iconic Canadian tuxedos 20 years ago. Take a look back at the red carpet moment.

By Lena Grossman Jan 08, 2021 8:46 PMTags
Watch: Happy Birthday, Britney Spears: E! News Rewind

Before we begin, let's take a moment of silence to reflect and remember those pop culture moments that came before us. Jump in a time capsule and look back at one year in particular in the early 2000s: 2001.

That momentous year, Hilary Duff became the most relatable teen when Lizzie McGuire premiered (Gordo, where art thou?), Russell Crowe won an Oscar for GladiatorShrek came out and made us question talking donkeys around the world and last but not least, Britney Spears and Justin Timberlake debuted their iconic denim-on-denim-on-denim-on-denim outfits to the world.

20 years ago today, The Mickey Mouse Club co-stars and pop star couple strutted their best (denim) stuff at the 2001 American Music Awards and forever changed what it means to have a red carpet moment.

There's so much to say about their sartorial decisions, yet words can hardly do it justice.

Britney Spears and Justin Timberlake: Romance Rewind

Let's start with the "...Baby One More Time" singer. Who knew denim could be made into a cocktail dress? No one—until Britney proved us all wrong.

Her strapless dress was tight on top and flowed elegantly to the ground. The bottom of the dress was filled with various shades of blue jean, almost making it seem like the outfit could really work as a day-to-night piece. Her diamond and silver studded belt sat loosely around her hips and matched perfectly with her purse, which was also denim with a sparkly strap. 

But we can't discuss the dress without mentioning her accessories. Oh yes, the accessories. She rocked a thick V-shaped choker (screaming early 2000s vibes) and mirrored it with a crystal clasp bracelet around her wrist.

Lest we forget Justin? Never.

His Canadian tuxedo was well-accessorized, too, and consisted of more separate pieces. Starting from the top down, there was the dark blue fedora/cowboy hat/all of the above because it can't even fit into one category of hat. The "ribbon" of the cap was made from a jean's waist with the button facing forward. Then, his ill-tinted glasses had a brown-purple hue to it and were clearly more for fashion's sake than sun protection.

This entire get-up will go down in history as one of the most unforgettable till the end of time.

His outer layer completely redefined what it means to wear a jean jacket. The Levi's coat looked like a blazer mixed with a sport coat. Unclear if the pocket flap led to an actual pocket (probably not).

His diamond necklace shimmered in the light and was made of the same material as his girlfriend's jewelry.

The "Sexy Back" singer's shirt didn't look like denim material, but camouflaged nicely enough with the rest of the outfit.

Watch: Happy Birthday Justin Timberlake!: E! News Rewind

Oh, those pants. Are these the jeans that launched a thousand lookalikes?

The bottoms were possibly created out of at least two different pairs of jeans. They were various shades of blue and filled with silver studs on top. The pants flowed and creased all the way down to his brown boots.

Over the years, some celebrities attempted to pay homage to the couple by wearing double denim outfits on the red carpet. For instance, Katy Perry wore a strapless denim dress to the 2014 MTV Video Music Awards and walked the carpet with Riff Raff, who wore a matching suit.

The "Toxic" singer later praised Perry for her decision to pay tribute to her. "Just when I thought the denim dress had retired....you bring it back! You looked amazing tonight bb ;)," she tweeted.

While a full throttle joutfit might raise some eyebrows nowadays, we'll never hold it against Britney and Justin for doing it.

To see more Canadian tuxedo moments, check out the gallery below!

Back to Basics

When attending the 2000 MTV Video Music Awards, Justin Timberlake and Britney Spears looked wonderful with their turtleneck sweater or little black dress. Their style, however, would change less than a year later.

The Reveal

'Twas a star-studded evening at the 2001 American Music Awards when Justin and Britney arrived to the red carpet with an outfit never seen before.

Red, Set, Pose

From the hat to the purse, there was SO. MUCH. DENIM.

What Are They Wearing?!

Photographers went crazy. Pop culture fans called their BFFs on an actual telephone to discuss the looks. And the look drove everyone crazy for all the right reasons.

Red Carpet Moment

Little did the Hollywood couple know that the red carpet look would become a pop culture fashion moment that would be shared with generations to come.

Perfect Match

Later in the year, the couple stepped out for a basketball charity event where they did it again—they wore matching outfits!

Denim Girls

It was the denim-on-denim look, however, that fans will never forget. At the 2014 MTV Video Music Awards, Katy Perry and Riff Raff put their own twist on the look. And for the record: Brit Brit called it "amazing."

Double Trouble

Blake Lively and Ryan Reynolds tried to recreate the look with a little help from Adobe Photoshop...

Costume Contest

YouTube stars Jake Paul and Tana Mongeau channeled the look for Halloween nearly 20 years after the initial award show...

Denim Darlings

Victoria's Secret model Devon Windsor and Johnny Dex did their best impression for one Halloween party...

Couple Goals

And although Miley Cyrus hasn't tried to replicate the look (yet), she was so inspired by the couple that it plays a role in who she dates. "I want a boyfriend that will wear jean on jean on jean with me," she once shared with the Nationalist in 2013.

Winner, Winner

Ultimately, Britney deserves credit for the matching look. "It was my idea," she once told MTV News. As for Justin, he doesn't plan on wearing something similar again. "It was such a crazy time and the world was different, the music industry was different. It was just a different time," the singer shared on The Project.