It’s Grammy Awards weekend 2026, and the city is buzzing. From Spotify’s Best New Artist party to packed record-label bashes, nominees are already in celebration mode as they eagerly await who will take home the night’s top honor.
Amidst it all, we’re digging through the archives and reflecting on how an artist’s first Grammy appearance is a rite of passage—both musically and fashion-wise. In other words, it’s a moment to stake their place in music history and express themselves through creativity and clothing.
Revisiting some of our favs’ very first red carpet appearances offers a fascinating window into the evolution of personal style, talent, and star power. Some celebrities took bold risks that later became signature statements, while others chose a more understated debut. Think: everything from SZA’s 70s-inspired tulle, bejeweled gown in 2019, to Whitney Houston’s one-shoulder, draped blue dress in 1986.
In honor of Grammys weekend, scroll on for inspiring Grammys fashion moments of the past. All a reminder that every celebrated career has a beginning—one often including a breakthrough performance and an unforgettable first red carpet dress. These moments stay with us as we watch stars reach new heights.
Kendrick Lamar made his first Grammy appearance in 2014, performing a mashup of “m.A.A.d city” and “Radioactive” with Imagine Dragons, though he won none of his seven nominations. Lamar wore a slim-fitting blue suit with a silk lapel collar, paired with black patent leather shoes.
SZA earned five nominations in 2019, including Best New Artist, for her breakout album Ctrl. She attended the ceremony wearing a silver, ’70s-inspired gown featuring a long tulle skirt, dramatic bell sleeves, and an intricately bejeweled bodice.
Doechii had a breakout year last year, becoming the third female rapper in history to win Best Rap Album and earning nominations in three additional categories, including Best New Artist. She made her first Grammy appearance in 2022, wearing a sculptural black high-low dress adorned with tulle bows.
Rihanna attended her first Grammy Awards in 2007, wearing a green Roberto Cavalli one-shoulder asymmetrical dress featuring a hip cutout, paired with dangling gold earrings and chunky gold bracelets and rings. She wasn’t nominated that year, but the following year she earned four Grammy nominations.
Tyler, The Creator made his first Grammy appearance in 2018, dressed head-to-toe in Louis Vuitton, featuring a blue wool jacket, a monogrammed scarf, and a white fluffy hat. He didn’t win his first Grammy until 2020, when he took home Best Rap Album for his 2019 project IGOR.
Beyoncé made her first Grammy appearance at the 42nd Grammy Awards in 2000 alongside Destiny’s Child, when their hit “Bills, Bills, Bills” earned a nomination. The group coordinated in soft shades of cream, with Beyoncé standing out in a two-piece cream ensemble adorned with cascading gems and a floor-grazing skirt. She now holds the most Grammy wins of any artist with 35 awards.
Leading the pack as the Black artist with the third-most Grammy Awards—behind Quincy Jones and Beyoncé—with 25 wins, he made his first Grammy appearance in 1974. He arrived in aviator sunglasses, a low flat-top haircut, and a ’70s-style embroidered white dress shirt, worn unbuttoned to reveal his chest.
Pharrell Williams, now the Men’s Creative Director at Louis Vuitton and a renowned rapper, producer, and songwriter, attended and won his first Grammy in 2004. He wore a crisp white suit jacket and button-up shirt, paired with blue jeans and a white belt.
Houston is set to receive a posthumous Lifetime Achievement Award at the 2026 Grammys. Her first Grammy appearance—and win—came in 1986, and she went on to earn six Grammy Awards over the course of her career. For that debut, she wore a one-shoulder, draped blue gown accented with a sleek, white shimmering shoulder strap.
Luther Vandross made his first Grammy appearance in 1991, where he won his first award for Best Male R&B Vocal Performance. He wore a cropped tuxedo jacket over a white shirt, paired with classic black suit pants.
