The Best-Ever Grammys Beauty Moments Are As Iconic As The Winning Albums

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 66th Annual Grammy Awards right around the corner — 7 p.m. ET on February 4, 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.

Bobbie Gentry, 11th Annual Grammy Awards

‘60s beauty trends have become so popular in the 2020s that Gentry’s voluminous layers, big lashes, and gold hoops are just as likely to be seen at a modern Grammy Awards ceremony. In 1968, the singer-songwriter’s style was cutting-edge.

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.

Diana Ross, 27th Annual Grammy Awards

You think music industry, you think 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.

Whitney Houston, 28th Annual Grammy Awards

Only 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

O’Connor’s relationship with the Grammys was 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

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.

Mariah Carey, 33rd Annual Grammy Awards

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.

Janet Jackson, 35th Annual Grammy Awards

When you’re a star of multiple mediums, nothing delights fans more than a crossover moment. 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.

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.

Britney Spears, 41st Annual Grammy Awards

If you were around in 1999, you know that Spears’ sleek-haired Grammys look made everyone you knew run out and buy a new flat iron. Similarly, her frosty-finish makeup helped bridge the gap between the ‘90s and the new millennium.

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. But those ‘00s crazes are back with a vengeance, making the vintage photo feel more like modern inspiration — especially Rowland’s incredible lip liner combination.

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, Madge made these retro flipped-out bangs her signature for the promotional cycle.

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.

Adele, 54th Annual Grammy Awards

Between Adele’s Old Hollywood hair, red lips, stunning cat-eye, and six awards, a star was born. She’s largely stuck to this now-signature aesthetic since, but it was never more fully realized than at the 2013 ceremony where she went all-in on gel eyeliner and the perfect matte lip.

Rihanna, 57th Annual Grammy Awards

Rihanna’s sweet pink Giambattista Valli ballgown was such a statement, she kept her makeup so minimalist — and beyond gorgeous. She let her natural beauty shine with just a bit of warm eyeshadow, the faintest hint of liner and mascara, and just enough face makeup to add a glow to her complexion. With her hair pulled back in an effortless bun, she’s just breathtaking.

Lana Del Rey, 60th Annual Grammy Awards

Playing into the feel of her music, Del Rey 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 as ethereal and otherworldly as her early records.

Cardi B, 61st Annual Grammy Awards

Cardi B and Mugler are a match made in heaven — and what hairstyle would you wear to your second-ever Grammy Awards other than a pearl-covered beehive? It’s Cardi’s most Libra-tastic look ever, and it’s clearly lucky because she walked away with the night’s top rap award for Invasion Of Privacy.

Billie Eilish, 62nd Annual Grammy Awards

It’s safe to say that nobody could pull off neon-green-and-black hair like pop star Eilish. Even with her face obscured by a semi-sheer Gucci mask, this look is all-time. You can even see her glossed pink lips through the rhinestone-covered mask’s gauze.

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.

Taylor Swift, 63rd Annual Grammy Awards

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.

Beyoncé, 64th Annual Grammy Awards

As the most awarded artist in Grammys history, of course Beyoncé has multiple spots on this list. She’s worn more avant-garde looks to the annual ceremony, but in terms of overall excellence, her latest appearance is top-tier. Her long, glossy mermaid waves absolutely shone on-stage as she collected her trophy for Renaissance.

Dua Lipa, 64th Annual Grammy Awards

Always one to push the envelope, Lipa went temporarily blonde for the 2023 Grammys, complete with extra-long wig for added drama. If her statement-making Versace getup and platinum hair wasn’t enough, she even factored in a dark red matte lipstick — incredible.