A 19-year-old Keys rocked braids, white sneakers and a black fedora at the 42nd Annual Grammy Awards Arista Records Pre-Grammy Party in 2000.
The following year at the 43rd Annual Grammy Awards, the singer went for a beige-and-brown leather ensemble at BMG’s post-Grammys party.
Riveting in Red
Keys wore a floral red halter gown (and some serious eye sparkles) at the 44th Annual Grammy Awards in 2001. It was a phenomenal year for her: she won five Grammys for song of the year, best female R&B vocal performance, best R&B song for “Fallin’,” best new artist and best R&B album for Songs in A Minor.
Keys posed with legendary music executive Clive Davis in 2002 at his annual Pre-Grammy Gala wearing a silk headwrap, white jeans and a crop top.
Keys and her mother Terri Augello snapped a photo with Kim Cattrall during Davis’ Pre-Grammy Gala at the Regency Hotel in 2003 in New York City. The singer went for an Asian-inspired look with chopsticks in her hair and a bold red lip.
The “Girl on Fire” singer chose 2003’s BMG Post-Grammy Gala carpet to send a message through fashion. She had on a forest green fedora and a cropped white jacket embellished with sequins that exposed her lower back and the words “THINK 4 URSELF.”
Sophisticated & See-Through
At Davis’ Pre-Grammy Gala in 2004, Keys went for a sleek low bun to let her sheer, cutout beaded top shine. She topped off the look with matching dangling earrings, a deep smoky eye and bright pink blush.
Basic Bottom, Party Top Part 1
Keys combined comfort and elegance with her 46th Annual Grammy Awards carpet look by pairing white jeans with an off-the-shoulder top that flowed all the way down to form a short train.
Basic Bottom, Party Top Part 2
After the show, Keys posed in the Grammys press room in a very similar outfit, swapping out white jeans for blue and off-the-shoulder for a diagonal bedazzled strap with a denim sleeve on her right arm.
Animal Print Party
At Davis’ 2005 Pre-Grammy Gala cocktail reception, Keys posed next to Diana Ross in an animal-print cutout top and sleek straight hair.
White & Gold
Keys wore a white floor-length gown with gold straps to the 47th Annual Grammy Awards. Her outfit perfectly complemented the four Grammys she won that year: best female R&B vocal performance for “If I Ain’t Got You,” best R&B performance by a duo or group with vocals for “My Boo,” best R&B song for “You Don’t Know My Name,” and best R&B album for The Diary of Alicia Keys.
Lovely in Lace
Keys and her then-boyfriend, music producer Kerry Brothers, coordinated their black-and-gray looks on the 48th Annual Grammy Awards carpet. That year, she was nominated for five Grammys: best female R&B vocal performance for “Unbreakable,” best R&B performance by a duo or group with vocals for “If This World Were Mine,” best traditional R&B vocal performance for “If I Was Your Woman,” best R&B song for “Unbreakable” and best R&B album for Unplugged.
Pretty in Purple
Keys went simple yet sophisticated on the purple carpet at Davis’ Pre-Grammy Gala in 2006, matching the event in her violet dress and romantic updo.
The singer wore a navy blue halter dress with a small pink clutch, statement earrings and a giant rock on her finger on the 50th Annual Grammy Awards carpet. The elegant ensemble made her look like a winner — which she was in two categories: best female R&B vocal performance and best R&B song for “No One.”
Strapless, Flowy, Fun
Singers Keys, Rihanna and Fergie stole the spotlight at Davis’ Pre-Grammy Gala in 2008 with their completely different looks. Keys went for a strapless dress adorned in a loud print, while Rihanna was covered up from the neck down and Fergie wore a plum gown with spaghetti straps. That year, Keys won a Grammy for best female R&B vocal performance for “Superwoman” and was nominated for best pop collaboration with vocals for “Lesson Learned” and best short form music video for “Another Way to Die.”
A glam Keys joined Serena Williams and Kim Kardashian at the 2012 Pre-Grammy Gala and Salute to Industry Icons event that honored Sir Richard Branson.
Husband Swizz Beatz and pal Pharrell Williams gave Keys her moment at the 56th Annual Grammy Awards, where she was nominated for best R&B album for Girl on Fire. The singer chose a stunning royal blue, deep-cut, floor-length gown and an updo for the night — and won the Grammy!
Nancy Pelosi and Keys showed strength and solidarity at the 2015 Grammys On The Hill Awards at The Hamilton in Washington, D.C. The ladies went for power suits — the Speaker of the House in red and Keys in black.
Dressed to Express
At the 60th Annual Grammy Awards in 2018, Keys posed in a black cutout gown with French braids and no makeup, while her husband took a stand against President Donald Trump with his coat.
Red-dy for Anything
Ahead of her hosting gig, the star struck a confident pose in her elegant crimson Armani Privé gown and jaw-dropping Bulgari jewelry. And she hinted at much more to come: ‘There’s so much in store,’ she tweeted.