8:23am PST, Jan 7, 2020
As the 62nd Annual Grammy Awards nears, Wonderwall.com is taking a look back 20 years ago to see what the biggest stars at the turn of the millennium were wearing on the 2000 Grammys red carpet… starting with this look! Britney Spears went full glam for her first Grammy Awards show in this stunning white gown with cut-out straps from Randolph Duke. The “…Baby One More Time” singer — who was nominated that night for two awards — paired the floor-length look with a matching white fur stole from Oscar de la Renta and a gorgeous glittering diamond necklace. Keep reading to see more eye-popping Y2K Grammys fashion…
Jennifer Lopez‘s dress made fashion history! J.Lo arrived at the 42nd Annual Grammy Awards in this plunging green tropical-print Versace gown that left little to the imagination. The silk-chiffon gown — which required copious amounts of double-sided tape — remains one of the most iconic looks to ever grace the red carpet.
Another artist who was up for her first Grammy Awards in 2000 was Christina Aguilera, who was nominated that night for best new artist (and won!) as well as best female pop vocal performance for her hit song “Genie in a Bottle.” Christina — then 19 — shimmered on the red carpet in this heavily sequined silver butterfly dress by Versace.
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The boys of *NSYNC — Lance Bass, Joey Fatone, JC Chasez, Chris Kirkpatrick and Justin Timberlake — arrived at the 2000 Grammy Awards, where they were up for two prizes (best pop collaboration and best country collaboration), in perfectly coordinated looks. Their matching ensembles included Lance’s zip-up black leather cowboy shirt, Chris’s chocolate cargo pants and Justin’s salmon button-up shirt — all of which clearly orbited around a fashion focal point: Joey’s flaming red-tipped hair.
We can’t handle the cuteness in this Feb. 23, 2000, pic. Not only did Lenny Kravitz — who was nominated for and won the Grammy for best male rock vocal performance that night for his song “American Woman” — have some major style of his own, but his daughter, Zoe Kravitz, was enjoying her own eclectic fashion moment. While Lenny kept things ultra cool in a chocolate leather jacket, slacks and shades, Zoe wore a kaleidoscope of textures and patterns including a floral and lace silk skirt, white tube top, orange leather jacket, curved-brim hat and super-comfy blue tennies. Most importantly, Zoe looked proud to be by her famous dad’s side.
Is it hot in here or is it just Faith Hill‘s seriously sexy black leather dress from the 2000 Grammys? Faith — who was nominated for best female country vocal performance for her song “Let Me Let Go” — came to the show looking like a snack in this plunging V-neck dress.
The late, great Whitney Houston was pretty in pink at the 2000 Grammys. Nominated that night for four awards, Whitney — who wore a hot pink gown with a wrap-style skirt and sheer rhinestone-embellished bust by designer Emanuel Ungaro — took home a trophy for best female R&B vocal performance for her song “It’s Not Right But It’s Okay.” She completed her look with a dramatic matching pink stole and sparkling diamond jewelry.
This photo was taken just five months before Farrah Franklin (second from left) quit Destiny’s Child. But on Grammys night in 2000, the quad squad was seen together wearing complementary cream outfits on the red carpet. The ladies — including Kelly Rowland, Beyonce and Michelle Williams — were up for their very first Grammy Award for best R&B performance by a group for their hit song “Bills, Bills, Bills.” While all donned two-piece looks, Beyonce was the only one to skip the lace and go for sparkling sequined fringe.
Who says cute can’t be comfortable? At the 2000 Grammy Awards, comedienne and TV personality Ellen DeGeneres donned a plum pantsuit and pink crew-neck tee with some easy-to-wear tennis shoes, allowing her to focus on having fun instead of worrying about a wardrobe malfunction or aching feet.
We just want to ask Sisqo one question: Why? At the 2000 Grammys, the “Thong Song” singer donned this cringe-worthy studded red leather getup with no shirt. He even had matching gloves and rose-tinted shades. It didn’t work then and it still doesn’t work today.
We’re saying yes to all three minidresses worn by TLC members Tionne “T-Boz” Watkins, Rozonda “Chilli” Thomas and Lisa “Left-Eye” Lopes at the 2000 Grammys. The trio were up for six awards that year and came dressed to impress in black-and-white minis and matching thigh-high sequined leg warmers. By the end of the night, the “Waterfalls” singers had won two new awards: best R&B album and best R&B performance by a group.
We completely forgot that actress Bridget Fonda once dated country music star Dwight Yoakam. The couple were arm in arm at the 2000 Grammys where Dwight was nominated for best male country vocal performance for his cover of Queen’s “Crazy Little Thing Called Love.” While Dwight looked like a handsome and mysterious cowboy in his neutral-hued attire, Bridget stunned in a golden button-up blouse and a shimmering floor-length red skirt.
We’re honestly kind of underwhelmed by Martina McBride’s 2000 Grammy Awards look. The “Independence Day” singer, who was nominated that night for best female country vocal performance for her song “I Love You,” arrived in this ankle-length white sequined chiffon and silk dress that wasn’t necessarily bad, but it was so boring that it almost made us fall asleep while we were writing this.
Who remembers when Kid Rock and up-and-coming actress and model Jaime King were an item? While the Michigan music star — who was nominated for two Grammys that night — went big-pimp style in a black tuxedo and white tie paired with a full-length fur coat, Jaime kept it simple and sweet in a sunshine yellow tiered and ruffled mini with a black shawl and matching pointy-toed black heels.
Shirley Manson — who was nominated for two Grammys along with her Garbage bandmates that year — arrived on the red carpet wearing a red, white and blue plaid school uniform-inspired look with black fishnets, white socks and red heels.
Sheryl Crow‘s 2000 Grammys look is an entire mood. Clearly still feeling the ’90s, Sheryl donned black leather pants, a black velvet V-neck crop top with bell sleeves, purple-tinted Lennon shades and a long statement necklace. That night, the “There Goes the Neighborhood” singer won the Grammy for best female rock vocal performance for her cover of the Guns N’ Roses song “Sweet Child O’ Mine.”
Limp Bizkit singer Fred Durst wore his usual casual attire — a red T-shirt, matching baseball cap, black track pants and black Adidas — at the 2000 Grammys even though his band was nominated for the first time for two Grammy Awards.
We’re not sure what to make of Missy Elliott’s 2000 Grammys look. The “Superfly” rapper, known for her creative and colorful tracksuit-inspired outfits, turned up in a royal purple pantsuit covered in razor blades. Maybe Missy was making sure no one could hug her if she won in category in which she was nominated that night: best rap album (for “Da Real World”).
Puerto Rican singer Ricky Martin was up for three awards at the 2000 Grammys. With then-girlfriend Maital Saban by his side, Ricky stunned in a black tuxedo with an extra-long jacket. Maital, in contrast, practically glowed in her sexy sequined baby blue skirt and sheer pink tube top.
It was a year before The Dixie Chicks would become pariahs of the country music industry, when Emily Robison, Natalie Maines and Martie Maguire were still on top of the world: At the 2000 Grammys — where they were nominated for four awards and won two — the trio skipped the matchy-match look so many other groups were doing and rocked their own styles. While Emily opted for a fuchsia-and-black halter dress with a deep V, Natalie went for a softer style in a blue suede skirt and ruched satin corseted top. Our favorite look, however, was Martie’s sexy white asymmetrical mini paired with knee-high boots and a stunning diamond chandelier necklace.
We love Canadian songbird Sarah McLachlan, who won one of three Grammys for which she was nominated in 2000, but we don’t love the brown satin A-line gown she wore to the show. Sarah’s strapless gown could have shined if she hadn’t mismatched it with a white shawl and beaded blue clutch, which together seemed to make the formal dress look awkwardly casual.
Macy Gray was one of the biggest stars to emerge at the turn of the millennium. But at her very first Grammy Awards show, the singer — who was nominated for best new artist and best female R&B vocal performance — wasn’t winning any awards for her royal blue fur-trimmed coat and matching pants. While her style at the 2000 Grammys left something to be desired, we do love the brilliant smile on her face and that gorgeous, multicolored choker around her neck.
We’re pretty sure Monica had a biker babe convention to go to after the 2000 Grammys. Wearing this rivet-studded black leather jumpsuit, the “The Boy is Mine” singer just needed a revved-up motorcycle on the red carpet to complete her look.
Broadway star Jane Krakowski turned up at the 2000 Grammys looking feisty and fierce in this red ensemble — crimson patent-leather pants and a matching sheer embroidered tank top.
Who remembers adorable Billy Gilman, the young country music singer who rose to fame in 2000 with debut song and album “One Voice”? The little 11-year-old star arrived at his first Grammys wearing a toothy grin and this miniature chocolate brown suit with a matching embroidered silk shirt.