If there’s one profession that can really appreciate the power of a creative, show-stopping red carpet hair and makeup moment, it’s musicians. As natural performers, musically-inclined celebrities always find a way to infuse pure creativity into their award show moments, be it with a standout lipstick or a full-on cosmetic costume. It makes sense then that so many of the greatest makeup moments of all time would happen at the Grammys, music’s biggest night. The best Grammys beauty moments span decades and genres — Beyoncé, Selena, Dolly Parton, and Lady Gaga, for example, might seem so different sonically, but they all know how to dominate the red carpet in their own way.
Examining the Grammys beauty looks from every year is some of the best insight into the trends of the day — Dolly Parton’s sunkissed ‘70s makeup, Whitney Houston’s fabulously feathered ‘80s haircuts, the beachy glamour of ‘90s-era Mariah Carey, and the loud-and-proud ethos of contemporary stars like Billie Eilish and Cardi B tell you as much as a textbook could. In recent years, too, it’s become de rigueur to match one’s Grammys look with the aesthetic of their latest album. It’s why Taylor Swift graced the red carpet with cottagecore buns in homage to Folklore, Madonna embraced disco motifs in her Confessions On A Dance Floor era, and Janelle Monaé reflected their signature retro sound with a jewel-accented pixie cut.
With the 65th Annual Grammy Awards right around the corner — 7 p.m. ET on February 5, to be exact — there’s no better time to revisit the most iconic makeup and hairstyles from the Grammys of yesteryear. Ahead, some of the all-time greatest Grammys beauty looks.
Lizzo, 63rd Annual Grammy Awards
Lizzo knows her way around a show-stopping accessory. At the 2021 Grammys, the singer paired her metallic, shell-pink gown — and nails — with oversized, jewel-encrusted barrettes that gleamed against her glossy, raven hair.
Madonna, 48th Annual Grammy Awards
She famously has many modes, but for many millennials and Gen Z-ers, Confessions-era Madonna just hits different. To accompany her disco-inspired album, Madonna made these retro flipped-out bangs her signature.
Diana Ross, 27th Annual Grammy Awards
You think music industry, you think Diana Ross — it just is what it is! Though already established as an all-time legend by the ‘80s, her glammed-up look from the 1985 ceremony is too good to not highlight. Her liner-packed smoky eye and signature curls will be a forever hit. Not unlike her music, actually.
Dolly Parton, 19th Annual Grammy Awards
All roads lead to Dolly. This look from 1977 is still so on-trend, from the larger-than-life hair to the long, doll-like lashes — fitting! Look closely and you’ll even see the country singer showing off an early example of nail art.
Lana Del Rey, 60th Annual Grammy Awards
Playing into the feel of her music, Lana Del Ray appeared on the 2018 Grammys red carpet encircled by a halo headband of twinkly stars. Paired with pale, luminous makeup and especially shiny hair, it’s ethereal and otherworldly.
Janet Jackson, 35th Annual Grammy Awards
When you’re a star of multiple mediums, nothing delights fans more than a crossover moment. Janet Jackson attended the 1993 Grammy Awards as a nominee and to present her brother with the show’s annual Legend Award, but played homage to her film career at the same time. Her red-toned box braids and white headband are a recreation of an identical style she wore in the cult-classic film Poetic Justice.
Whitney Houston, 28th Annual Grammy Awards
Only Whitney Houston could manage to look so ‘80s and so classic at the exact same time. While her big, feathered curls and dramatic makeup are certainly aesthetic hallmarks of the decade, her timeless features and brushed-up brows helps her 1986 Grammys look hold up even today.
Sinead O’Connor, 31st Annual Grammy Awards
Sinead O’Connor’s relationship with the Grammys is famously strained (she’s actually the only artist to ever refuse a Grammy award, calling the Recording Academy unfairly exclusionary and biased), but the musician-activist’s signature shaved head on the red carpet, itself a conscious act of defiance, will forever be iconic.
Paula Abdul, 32nd Annual Grammy Awards
Paula Abdul’s cheerleading roots come through in her shimmery, scrunchie-topped look at the dawn of the ‘90s, and her era-perfect makeup (the terracotta blush! the frosty brown lipstick!) completes the retro package.
Taylor Swift, 63rd Annual Grammy Awards
Taylor Swift showed up to collect her record-breaking third Album of the Year award in a wildflower-themed outfit matching the motifs and aesthetics of her album, Folklore. Her makeup, all rosy-bronze and cottagecore, mushroom blonde hair help complete the effect.
Mariah Carey, 33rd Annual Grammy Awards
Mariah Carey’s legend status transcends decades, but her early years in the spotlight are truly something to behold. At the 1991 Grammy Awards, a young Carey showed off her hone-toned natural curls with some (still incredible to this day) brown lipstick — a quintessential ‘90s staple.
Selena, 36th Annual Grammy Awards
The iconic Selena Quintanilla-Pérez appeared at the 1994 show with a cascading, curled updo and her signature makeup look, rich ruby red lipstick with glamorous arched brows. It’s been nearly 30 years and the consensus remains — anything for Selena.
Billie Eilish, 62nd Annual Grammy Awards
It’s safe to say that nobody could pull off neon-green-and-black hair like popstar Billie Eilish. Even with her face obscured by a semi-sheer Gucci mask, this look is all-time.
Destiny’s Child, 44th Annual Grammy Awards
Beyoncé, Kelly Rowland, and Michelle Williams hit on so many 2002 beauty trends: chunky highlights, sheeny lip colors, and frosted eyeshadow.
Jennifer Lopez, 53rd Annual Grammy Awards
It’s hard to beat J.Lo’s green dress from the 2000 Grammys, but if you’re looking at hair, this long, perfectly highlighted style from 2011 is the pic to bring to your colorist.
Adele, 54th Annual Grammy Awards
Between Adele’s Old Hollywood hair, red lips, stunning cat-eye, and six awards, a star was born.
Britney Spears, 41st Annual Grammy Awards
If you were around in 2000, you know that Britney Spears’ sleek-haired Grammys look made everyone you knew run out and buy a new flat iron.
Lady Gaga, 52nd Annual Grammy Awards
Lady Gaga had just burst onto the scene when she attended her first Grammy Awards in full Fame Monster-era regalia. Believe it or not, her dip-dyed yellow wig, smoky eyes, and mod-pink lipstick made up just one of her looks that evening.
Cardi B, 61st Annual Grammy Awards
Cardi B and Mugler are a match made in heaven — and what hairstyle would you wear with vintage Mugler other than a pearl-covered beehive?
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