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Turning Heads: 20 Most Iconic Grammy’s Looks From The 2000’s (& 5 That Fell Flat)

With the 61st Annual Grammy Awards coming up February 10th, fans are already gearing up to get cozy and watch the next best thing to the awards show itself—the red carpet strutting, of course!

A time for everyone's favorite stars to show off their personal style, the red carpet portion of the Grammys is always a treat to tune into and has been home to some of the most iconic ensembles in celebrity history.

From Jennifer Lopez's absolutely unforgettable green Versace dress to the top girl groups of yesteryear such as TLC and Destiny's Child all rocking matching outfits, it's clear that the Grammy Awards are just as much about fashion as they are about music.

The 2000s were a time when celebrities really experimented, too. With some of these stars truly going on to craft lasting professional paths for themselves, the 2000s really saw them coming into their own and using the hordes of paparazzi on the red carpet to truly put them on the map, establishing themselves as the next big thing in the music industry.

Although some of these choices may look absolutely bizarre, they've certainly gone down in pop culture history as iconic. Here's a countdown of the 20 most memorable moments from the 2000s Grammys, plus five looks that left fans wanting more.

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25 Britney Spears And This Iconic Number, Making Her Look Like A 2000s Marilyn

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Britney graced the red carpet in 2000 with this simple yet very sultry white dress and furry boa draped on her arms.

With the obvious resemblance to Marilyn Monroe being evident, Britney looked absolutely breathtaking!

While many stars have channeled the iconic Hollywood starlet in the past, Britney is very vocal with her adoration for Marilyn, which she still maintains to this day. As per Daily Mail, the pop star reportedly likes to have a collection of Marilyn's movies waiting for her at any hotel she visits, and she carries books on the late actress everywhere she goes.

24 Destiny's Child, And The Time They Served The Red Carpet With This Metallic Set In 2001

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Back in the early 2000s, Destiny's Child was at the height of their trajectory as a fearless girl group, known for their music but also their fashion sense—which usually saw them coordinating to perfection.

The brainchild behind all the coordinated outfits was Beyoncé's mom, Tina Knowles, who made them all herself, stitching up extravagant and original looks, making the girls all look like queens. Since going solo, Queen Bey has definitely upgraded to some hefty designer looks, but looking back at her style while with the rest of her Destiny's Child squad is simply iconic!

23 Christina Aguilera's Look At The 2001 Grammys, Since It Was At The Brink Of Her 'Dirrty' Phase

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Christina Aguilera and Britney Spears both rose to fame as teen pop queen rivals at the end of the '90s and fought for the crown all throughout the start of the early 2000s, too.

Since they both had such squeaky clean images, it was Christina who was the first to try and shed hers too, giving birth to her Dirrty phase, and "that" iconic music video to support it.

Her look at the 2001 Grammys was at the brink of shifting into this more adult phase and saw her rocking a pink dress with a very plunging neckline, cornrows, and very dramatic makeup.

22 Pink, Because She Actually Had Pink Hair At The Time

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While Britney Spears and Christina Aguilera were busy fighting for the innocent teen pop star crown, Pink was busy making her fame out of being the chick who told it like it was—with a short, androgynous pink haircut.

According to E! News, in an early interview to promote her debut album in 2000, Pink explained her stance in the pop industry. "The thing about me was I always knew when to draw the line. My thing was I was as [outspoken] as they came. If everybody was walking in a single-file line, I was walking backwards, diagonal over here. I'm going to make people follow me. I'm not going to follow y'all. I'm going to do what I want and hopefully you'll join along. And if not, I'm fine by myself."

21 Flat: Britney Spears And Alicia Keys, Who Both Unfortunately Wore Two Very Pirate-Inspired Get-Ups

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Although both Britney and Alicia look absolutely iconic in this photo together in sheer 2000s pop star perfection, their outfits are, arguably, eyesores. Both have seemingly acquired a bizarre, 2000s take on a pirate-inspired look, complete with tassels, fringe, and outright strange fabrics.

Regardless of her look, Alicia Keys still walked away with three Grammy Awards, as she was a leader of the "neo-soul" musical movement at the time.

Britney, on the other hand, still didn't recover from her loss to Christina Aguilera a few years prior as Best New Artist, and only saw her win two years later in 2004 for Best Dance Recording for "Toxic."

20 OutKast's Combo Of Outfits, Since They Were Outlandish

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OutKast's André 3000 and Big Boi were definitely influential in their rap profession and had a flair for style, too. The duo started off dressing safely, like many other hip hop artists of their time, but it was with the release of Stankonia in 2000 that saw the two really start to experiment both with their sound and their look.

Years ahead of their time in terms of their sartorial prowess, OutKast is still looked at fondly for all of the elaborate getups they rocked together. The 44th Annual Grammy Awards were no different, and as seen above the duo certainly turned heads.

19 Missy Elliot And This All-Pink Tracksuit, That Only She Could Pull Off

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A hip-hop legend and trailblazer for all women who didn't fit the cookie-cutter mold of the time, Missy Elliott always marched to the beat of her own drum from her elaborate music videos to her own personal style.

Usually seen sporting things that most of us wouldn't dream of pulling off, she sports many looks with ease, especially her formal tracksuit.

Missy was seen rocking the above ensemble in 2003 when she scooped up a Grammy award and looked flawless in her pink velour Adidas sweatsuit. She accessorized with a bandana, fuzzy golf cap, and fresh white sneaks and socks. To top her look off, she was seen blowing pink bubblegum the same shade as her tracksuit.

18 When Beyoncé Managed To Make A Baby Blue Prom Dress Look Utterly Flawless

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Sporting a beautiful Elie Sabb Spring 2008 Couture dress during the 2008 Grammy Awards, Beyoncé simply looked like a fairytale princess. What probably would probably look like too much on most, Bey somehow made herself look like a flawless powder blue and silver mermaid.

Since this look, Beyoncé has really matured her look, donning more sophisticated and elaborate pieces that really play around with textures, patterns, and even lace or feathered details. Although we think the Elie Saab dress suited the time perfectly, it's so wonderful to see how far Bey has come with her style, graduating to looks that truly match the diva status her fans have given her!

17 Flat: When Kanye Wore These Very Aggressive Sunglasses For No Particular Reason

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Kanye West is known for his sartorial prowess, and he's definitely rocked a variety of different looks since hitting the scene in the mid-2000s, but he's also had his fair share of mishaps, too.

In 2006 he decided to channel Prince's "Purple Rain" days for his performance, which consisted of aggressive sunglasses, white gloves, and a lilac-colored tuxedo.

It's not the first time the rapper wore bizarre eyewear. Two years later he would rock his slatted glasses during his "Stronger" performance and, unfortunately, made the shutter shades trend with his fanbase worldwide.

16 Lil Kim, And The Time She Rolled Up In An Entirely Matching Red Set And Chanel Motorcycle Helmet

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Before the likes of Nicki Minaj and Cardi B, there was Lil' Kim, one of the biggest female rap stars of the era, with a bold and outrageous style that would make her contemporaries today look modest. Her looks have been so iconic, in fact, that they've been recreated for countless costumes, most famously when Miley Cyrus recreated her signature mermaid look for Halloween in 2013.

The above outfit in for the 2002 Grammy Awards is no different, as Lil' Kim rolled up to the red carpet in what looked like an update on Michael Jackson's "Thriller": red leather pants, a bikini top, a matching red jacket, Chanel sunglasses, and a motorcycle helmet to go with the ensemble.

15 The Time Beyoncé And Prince Collaborated And Their Outfits Made Fans Howl With Joy

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Beyoncé dazzled in 2004 and served fans with two separate yet fabulous looks. The first was for her iconic performance with Prince, which dazzled fans as soon as she stepped out in her pink sequined and feathered minidress.

Prince took the stage first in a purple suit while he performed "Purple Rain" but was soon joined by Bey who then transitioned into a very playful take on "Baby I'm a Star" before taking over the stage with her backup dancers with "Crazy in Love."

With the crowd going wild, Prince added some electric guitar pizzazz to the song before the duo sprung into “Let’s Go Crazy,” with Beyoncé slamming the tambourine and dancing around Prince.

14 And Then Later On Queen Bey Made Sure Her Dress Matched All Her Awards

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Like the queen that she is, Beyoncé wasn't satisfied with her look after her performance with Prince, she decided to change things up again—this time matching the numerous Grammy awards she proceeded to win.

This was her first time walking the red carpet since going solo (the rest of the time she was seen with her former Destiny's Child bandmates), and we have to say—what a way to make an appearance wearing gold on gold, complete with that fabulous necklace. The dress was form-fitting and gathered at the front, while the back had an extremely low back—a sultry look for the icon.

13 Flat: M.I.A. And This Bizarre Print That Was A Bit Of An Eyesore

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M.I.A. worked the red carpet in 2009 while pregnant, and although we applaud the silhouette she chose for her dress, we were left feeling a bit dizzy from the bright colored print. Completing her look with neon high-tops, she then proceeded to perform with TI, Jay-Z, and Lil Wayne and sample her hit "Paper Planes."

According to Daily Mail, she later admitted that she was afraid her performance would induce labor.

"'When I read these books on childbirth, they are like, 'If you want to induce labor, try having a game of arm wrestle with your friend. I am like, "Oh my God, my option isn't an arm wrestle - it's like being onstage and with Jay-Z and Lil Wayne and Kanye and TI."

12 When Christina Aguilera Served Us With Her 2000s Version Of A Flapper Outfit

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Truly playing around with her look in the early 2000s, Christina Aguilera saw many transformations, from her humble beginnings as a wholesome teen pop star, to dramatically trying to turn herself into the ultimate starlet. 2004 saw her changing things up again as she became a brunette and sported an Atelier Versace Dress, showing off her burlesque side with a feathered neckline, sequins, and diamonds. She completed her 2000s take on flapper fashion with old Hollywood ringlets and very dramatic makeup.

The following year would see her completely transitioning into old Hollywood glam, where she looked like the iconic Marilyn Monroe.

11 When Lisa 'Left Eye' Lopes Went To The Grammys In A Head-To-Toe Fuzzy, Tan Outfit

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TLC would end up scooping up three Grammy awards in 2000, so it's no wonder the girl group trio wanted to look their best—especially Lisa 'Left Eye' Lopes.

We're in love with her fuzzy, all-tan outfit, as she matched her skirt to her cropped sweater, and even included a matching bucket hat.

Definitely a trend-setter in her own right, this look is something that's trending yet again in 2018, with millennials everywhere loving the fuzzy top trend that was so in at the end of the '90s and beginning of early 2000s, along with the bucket hat, which is finally making a comeback.

10 A Very Young Aaron Carter In This All-White Ensemble

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A smug yet young Aaron Carter greets us with this iconic, all-white suit that he donned during the Grammy Awards in 2000.

Bursting onto the scene when he was barely 10 years old in 1997, Aaron opened solo for his older brother, Nick Carter, with a cover of The Jets' "Crush on You." This led to his own record deal and while his self-titled debut album did alright, his 2000 album, Aaron's Party (Come Get It), went triple platinum, causing the youngster to have the swagger and confidence to grace the red carpet with ease.

9 Flat: Avril Lavigne's Outfit Which Was Very Typical Of Her, Yet Still Turned Out To Be A Bit Boring

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Hitting the mainstream pop industry by storm in 2002, Avril Lavigne was the anti-pop star—the answer to all the girls that didn't necessarily relate to the likes of Britney Spears, Christina Aguilera, and Mandy Moore.

At the height of her success in 2003, she decided to grace the red carpet in true Avril fashion, rocking baggy dress pants, a button up, and an oversized menswear blazer with the words "Rock On" taped inside the lining.

Although we love that she went for a gender-neutral look and really didn't succumb to the mold happening at the time, we still wish she wore something a bit more memorable that stuck out from the usual looks she served us with.

8 When Christina Beat Britney For 'Best New Artist' And Looked Like A Smug Discoball

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Christina Aguilera and Britney Spears both hit the scene around the same time, as teen pop sensations at the end of the '90s. Compared right from the get-go, the girls were pegged as rivals, and when the time came for a Grammy award for Best New Artist in 2000, all eyes were predicting Britney to be the winner. Although she's been regarded as the Princess of Pop ever since ...Baby One More Time became the best-selling album by a teenage solo artist, Christina ended up taking the Grammy due to her incredible powerhouse vocals.

This look is iconic not just because she looks like a shining disco ball, but because of the significance the moment had in the world of pop.

7 The Duff Sisters, Whose Looks Were 2000s Pink Perfection

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The Duff sisters were truly teen It girls of the 2000s, with Hilary starring in her own Disney TV show, Lizzie McGuire, while her older sister Haylie was paving her own path as an actress, first with her breakout performance in Napoleon Dynamite followed by guest starring on Seventh Heaven.

For Hilary, however, starring in her own show wasn't enough; she also pursued her own pop stint in 2002, perhaps gaining an itch from her first time at the Grammys in 2000.

Her dress was a teenage girl's dream: pink babydoll fitting complete with a ribbon and all-around shimmer.

6 Britney Spears And Her Rhinestone Top, As She Was Such A 2000s Fashion Icon

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Britney Spears was a fashion icon of the early 2000s, a pop princess who was always slaying with her outlandish outfits. The above photo where she rocked this rhinestone top was at Arista Records' Pre-Grammy party in 2000. She paired her look with low-rise, white pants and looked like the ultimate '00s It girl.

With the early 2000s coming back into fashion as of late, replicas of iconic It girl outfits are cropping up, and Britney's rhinestone top is no different. Our affinity to put rhinestones on everything is back in full force, paying tribute to quintessential '00s style.

5 Flat: The Time Jewel Thought It Was A Good Idea To Wear A Bedazzled Playboy Tee To The Grammys, Making Her Slightly Underdressed

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The Grammy Awards are a time to dress up and really strut your stuff, with celebrities showcasing their fashion prowess just as much as they're there to celebrate their achievements in music.

That's why fans were so surprised to see Jewel on the red carpet in 2000 looking slightly underdressed in a bedazzled, blue Playboy tee, which she completed with a black cardigan and short, pink nails.

Perhaps she learned after all the criticism of this look because Jewel's future award show appearances found the singer stepping up her game and glamming herself up in gowns and short sequined numbers.

4 Mary J. Blige And This Entirely Yellow Ensemble Complete With Fur And Sequins

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Starting her musical trajectory off in the '90s, by the time the 2000s came around, Mary J Blige was already a seasoned pro at awards shows and red carpets. Staying true to her too-cool aesthetic, Mary looked absolutely stunning in a canary-yellow fur jacket and a shimmering yellow cocktail dress. She completed her look with a matching bag, shoes, and her blonde hair, making her match to perfection.

Later on, after the red carpet, Mary sauntered onto the stage in all her yellow glory to accept her award for best pop collaboration with vocals for "Whenever I Say Your Name."

3 When Ok Go Literally Blended Into The Red Carpet

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Ok Go have always been known for being oddballs. Their breakout music video for "Here It Goes Again" went absolutely viral, as the four members performed a synchronized dance on moving treadmills. Since it came out in 2006, it has been viewed more than 37 million times.

A year after their hit single came out, they were at the Grammys in the above outfits that essentially made them blend into the red carpet.

According to Insider, they told People magazine at the time, "We're dressed in the future — the future dressed us. This is actually us in an hour." They then proceeded to win Best Music Video for "Here it Goes Again."

2 Jennifer Lopez And The Most Iconic Grammy Dress Of All Time

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Jennifer Lopez's green Versace Grammy dress from 2000 is probably the most iconic awards show dress of all time. It's so well-known, in fact, it even has it's own Wikipedia page. Immediately turning heads and making headlines across the globe, the dress was bold for its time, a sheer fabric cut with a very low neckline that extended all the way down to J.Lo's navel.

This look is still to this day remembered in popular culture so much so that just last month Versace closed its pre-fall 2019 runway show in New York by returning to the exact same silhouette, with simply an updated, colorful heart pattern.

1 Not Technically From The Grammys, But Is Any List Complete Without A Mention Of Britney And Justin In Their Most Iconic Red Carpet Look Together?

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No list of award show style would be complete without an honorary mention of Britney Spears and Justin Timberlake—a couple at the time—both rocking matching denim, a look so iconic that it's been repeated countless times in the past little while by celebrities all looking to channel the iconic duo.

Technically not from the Grammys, the look was from the American Music Awards in 2001, when the duo were both at the height of their respective musical paths.

Professing their love for one another and genuinely being seen as #RelationshipGoals, many stars afterward have tried to re-create this look, most notably Katy Perry at the 2014 VMAs and Ryan Reynolds and Blake Lively.

Sources: Daily Mail, Insider, E Online

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