The Prettiest Grammys Beauty Looks Ever

For the music event of the year, the industry comes out in full force. And because many musicians have dynamic, aesthetically driven personas, Grammys fashion and beauty is a sight to behold. The red carpet is often where musicians choose to debut new looks, from architectural wigs (Nicki Minaj) to hair inspired by Dolly Parton (Miley Cyrus)—some for one night only, others marking a new era for the performer in question.

From the over-the-top to the enviable, these are the coolest beauty looks in Grammys history.

Lil' Kim

While her VMAs outfit will probably be Lil' Kim's most notorious look, I'm quite partial to this sparkly number with lots and lots of gold. With the red hair and matching red lip, she looks like a very bejeweled Poison Ivy.

Doja Cat

Doja Cat's hair and makeup is usually a work of art, and this is no exception. This deep cat-eye and no-eyebrows almost feel like a trompe l'oeil painting, a work of visual trickery that makes you do a double take. Also I love her frosted '90s lipstick.

Bonnie Raitt

The blues singer-songwriter is known for her red hair with just a touch of white at the front. So even though this isn't out of the ordinary for Bonnie Raitt, it's still an iconic look. Part Cruella De Vil, part Rogue from X-Men, all cool and surprising.

Nicki Minaj

Nicki Minaj joked that this hair was natural, which I appreciate. This wig is an architectural feat, from the animal print on bottom around her head (matching her outfit, no less!) to the sky-high cloudlike body with black streak running through it.

Miley Cyrus

Miley Cyrus is a master of reinvention, and her hair and makeup play an important part in her chameleon-like evolution. This enormous bouffant is an obvious reference to Dolly Parton (Cyrus' inspiration and her godmother!), and while it was divisive, I like it.

Madonna

It's probably not an accident that I really like Madonna in her sleek and stylish eras—this, in 2006, was her evolution into modern superstar that leaned on the decade's influences (pink lip gloss, carefully blown out hair) but made them all her own.

Dua Lipa

This is not the only time Dua Lipa will be on this list. I like her interesting fashion and beauty choices, and this 2021 outing was thought of as an ode to Cher that features long, lustrous hair and 70s-appropriate lavender eyeshadow, plus one heck of a dress.

Solange Knowles

Solange Knowles has always paired her unique sound with an equally unique style—and the red carpet pundits have loved her for it. For the year she won her first Grammy (2017), she swept her hair up on top of her head in a "towering" updo that remains legendary today.

Rihanna

I could have chosen any manner of hair and makeup for Rihanna—she's ever-evolving and never misses the chance to do something striking. See also: this red curly wig in 2011, which could make anyone else look like a lion but somehow just makes her cooler.

Katy Perry

Katy Perry's choice of outfit was the clear winner here (she wore wings! To the red carpet!), but she chose a divine complementary beauty look: blue eyeshadow on her eyelid, and green shadow under the eye, to match the green and blue reflective light from the top of her dress.

Lizzo

When Lizzo went to the 2023 Grammys as a literal rosebush (then dramatically removed her hood, to tremendous effect), it was a fashion look for the ages. The matching orange eyeshadow and artfully spiky lashes ensures that her face doesn't get lost amidst the florals.

Gwen Stefani

Leaving aside the ultra-thin brows that I hope we never see again, Gwen Stefani's hair buns are a fun '90s throwback that I forgot was incredibly popular. Stefani could pull off an extreme beauty look with the best, but this gray eyeshadow and deep lip color is actually a little reserved for her.

Phoebe Bridgers

Phoebe Bridgers' cool skeleton outfit is incredibly detailed (zoom in and note the gorgeous beading!), so her makeup is similarly graphic: black cat-eye on the eyes, deep so-red-it's-almost-black lipstick. Add in her nearly white hair, and it's incredibly thoughtful.

Courtney Love

While Courtney Love sometimes favored a grungier aesthetic, in keeping with her music (think: black slip dress, messy wavy hair, red lipstick), this is a surprisingly romantic look from the singer. I love the Coachella-worthy crown and vivid pink makeup.

Alicia Keys

With her signature braids in a full updo and extremely sequin-adorned eyes, Alicia Keys is defining early '00s glamour. It won't be the first time I make this note, but dressing to match your future awards is an impressive thing to do, especially when it results in this photo.

Bette Midler

Wearing a vinyl record on your head on music's biggest night might be considered on-the-nose for most people, but when you're Bette Midler (and therefore a legend), it's probably something you just felt inspired to do on a whim. And you're pulling it off perfectly.

Grace Jones

This has likely made the list of "wackiest red carpet looks," but Grace Jones looking like a literal lampshade is true icon behavior. That deep, deep blue eyeshadow (very appropriately '80s) and red lip and blush is the kind of maximalism I'm here for.

Sinead O'Connor

A few years before she infamously ripped up a photo of the Pope on live television, Sinead O'Connor was wearing a t-shirt with the Virgin Mary on it (foreshadowing!). It's a little hard to see in this photo, but she's also got a bullseye drawn into the side of her buzzcut.

Erykah Badu

Erykah Badu's towering head wrap was a signature part of her style and a powerful statement about Black femininity in the music industry. I love this yellow version, particularly with the matching yellow and red pin on the side, and her beyond-minimal makeup.

Dua Lipa

Wearing a bold, belted Versace outfit once worn by Cindy Crawford, Dua Lipa looks incredible here. My favorite part is the visible roots, which match the black in the outfit, and the bold brows and lips ensuring that she doesn't get lost in the dress.

Shania Twain

With a few small tweaks, this classic Shania Twain look wouldn't look that out of place today. Classic leather jacket: check. Brown-pink shiny lip gloss: check. Peachy blush: check. Smoky cat-eye: check. Pretty, piece-y, half-up hairdo: we have a winner!

Toni Braxton

I just really appreciate this photo of Toni Braxton proudly holding up her Grammys. The dress is appropriately glamorous, the hair is characteristically short, and the eye makeup is dark and dramatic. I also appreciate that she veered from the obvious red lip choice.

Lady Gaga

If you're going to dress and perform as David Bowie, really lean in. Lady Gaga's feminized take on Ziggy Stardust is actually pretty impressive—which makes sense, because she never goes halfway on anything—and my favorite part is the sparkly blue eyeshadow.

Christina Aguilera

When Christina Aguilera infamously beat Britney Spears for a Grammy (and seemingly settling once and for all—as the media spun it at the time—that she was the better singer), she dressed for glamour. The deep blue eyeshadow and shiny lip gloss are a thoroughly Y2K vibe.

H.E.R.

If you're unfamiliar, H.E.R. historically wore sunglasses (yes, even on the red carpet) as a form of anonymity. So it makes sense that her eyeshadow here matches, and the contrasting red lip helps provide contrast. And the hair is spectacular.

Cardi B

For this incredibly sculptural dress (it's probably one of the loveliest things I've ever seen her wear), Cardi B had to pull off a makeup look that complemented the fabric literally covering half her face: just a touch of blue eyeliner plus an intense liner on her lips.

Lana Del Rey

A starry halo on Lana Del Rey is very par for the course. A similarly graphic makeup look on her face brings similar energy and cohesion: that's an impressively long cat-eye, and the deep mauve makeup is a more striking alternative to nude. Very ethereal.

Whitney Houston

Whitney Houston, in silver sparkles, with a huge grin and Grammy in hand: that's it, that's the tweet! That soft and romantic updo is a great choice, and the deep red lip and smoky eye give so much depth to her look. (She's also wisely keeping jewelry to a minimum: the dress is the jewelry.)

Taylor Swift

Taylor Swift was riding high at the 2024 Grammys, and her look has the intensity to match. The hair and makeup is very Old Hollywood, with the Veronica Lake-esque side part, blood red lip, and precise cat-eye. I also love the watch choker (which I'm sure is probably an Easter egg of some kind!).

Selena

We got a glimpse of how award-winning the late Selena Quintanilla could have been when she attended the 1994 Grammys (and won). This enormous beehive and red lip was also an indicator of her natural fashion sense and taste. I wish we'd gotten to see it more.

Beyoncé

This outfit has to go into the Grammys hall of fame: Beyoncé, pregnant, surrounded by her signature color (gold), looking every inch the superstar. The beauty is almost beyond the point, but of course the singer leaned in with long golden hair and eyeshadow with a touch of sparkle.

Jennifer Lopez

The dress that broke the internet! (Serious, it led to the invention of Google Image Search.) It's funny that I never assessed her beauty before, but the matching blue eyeshadow is a pretty inspired choice, and the peachy lip color is pure perfection.