The MTV Video Music Awards is a category all its own. More casual than the Grammys, more sophisticated than the Kids' Choice Awards, and more outrageous than any of its counterparts, the VMAs were legendary in the '80s and '90s for over-the-top performances. Beauty-wise, VMAs looks have run the gamut, with some performers leaning edgy and minimal and others nodding to the show's playful roots with their hair and makeup.
Below, the coolest beauty looks from the VMAs.
Britney Spears
For a VMAs appearance that was billed as a comeback after a tough couple years, Britney Spears went full Britney with crimped hair, lip gloss, and perfectly applied black liner and eyeshadow. Fans of hers cheered wholeheartedly to see her looking so well.
Doja Cat
Every time I think I've seen it all from Doja Cat, she comes out with something even more avant-garde and bad*ss. The strategically placed crystals around her white eyeshadow is already cool, but the spidery lashes matching the actual crystal spider at her ear? Even cooler.
Björk
Björk was marching to the beat of her own drum long before the rest of us had caught up to her, including with her signature hair buns that defined her style in the '90s. I actually really love this look, with some dark eyeshadow and otherwise minimal makeup.
Renee Rapp
Gen Zers are huge fans of Renee Rapp (as are older people! I love her!), and here's she's giving us some of her trademark style: voluminous blonde hair, with visible roots, a lot of black eyeliner that's impressively defined but still subtle, and just a touch of color on the lips.
Gwen Stefani
Gwen Stefani really loved decorative crystals back in the day. Here, combined with matching blue hair, done up in buns, it's the kind of edgy-feminine aesthetic she was known for in the '90s. Looks great on her...is also impossible to replicate, as I can attest.
Lizzo
Lizzo stole the show at the 2022 VMAs with a huge navy blue gown (that almost matched to the black carpet she was walking on!). She was giving people "princess of the underworld" vibes in a major way, and the lip ring and blue lipstick was exactly appropriate for this OTT event.
Drew Barrymore
Drew Barrymore very famously wore daisies in her hair at the 1998 Oscars, but did you know she channeled the same style a few years earlier at the VMAs? Barrymore was our style gal of the '90s, and the daisy was our collective symbol, so this is a perfect matchup.
Lauryn Hill
Largely considered one of the best rappers of all time, Lauryn Hill is also known for a style that's all her own. In 1999, when she won four Moonmen awards, she was impossible to miss (and red-hot, literally). The red shades are a cool Y2K touch to finish off the look.
Nicki Minaj
Nicki Minaj has debuted some wild looks over the course of her career, but I particularly enjoy this two-toned pink and blonde 'do. In a synergistic moment, the hair and lipstick match her Barbie-pink dress, but the rest of her makeup is relatively simple.
Sinead O'Connor
While Sinead O'Connor's signature bald head is now inextricably linked with her persona, at the time it was revolutionary (and semi-controversial). With a pretty cat-eye and a touch of color on her lips, she looks perfectly balanced, and ready to rock.
Billie Eilish
While she often goes over-the-top in hair color and styling, Billie Eilish can give us a minimalist beauty moment that's just as impressive (she wasn't even wearing nail polish here!). The relatively new blonde hair, cut into a shag, was just deeply cool.
Mary J. Blige and Lil' Kim
Leaving aside the "pasty" of it all (Lil' Kim's outfit made some people very mad!), the purple wig is genuinely very stylish. And she and Mary J. Blige are wearing similarly long lashes and dramatic eyeshadow with some strategically deployed lip gloss.
Katy Perry
If you're going to reference a pop culture moment, go all in! If you're unfamiliar, Katy Perry is referencing Britney Spears and Justin Timberlake's double denim outfits, just with some modern touches (the red lipstick, the nose ring, the deep cat eye).
The Spice Girls
There's a lot to unpack here—this late 90s aesthetic really defined our style for a couple of years—but the fact that they are all (except Posh) matching in blue eyeshadow is a cute matching moment that I think I missed the first time. And then all their lip colors are different!
Taylor Swift
We get some great fashion and beauty from Taylor Swift, generally and when she switches things up at the VMAs. This 2019 look is more patterned and colorful from her than usual, and the bright red lip draws the eye upwards expertly towards her face.
Alanis Morissette
I have always been a fan of Alanis Morissette's style—she's always leaning heavily on her gorgeous hair, and for good reason, but she never feels overly styled. This is a refined version of her classic style, with some long layers but still that traditional minimal makeup and natural beauty.
Miley Cyrus
Any list of VMA beauty looks would be incomplete without Miley Cyrus, who is always evolving her aesthetic. But her jump to short hair, fashioned here in a sky-high pompadour, will always be the moment I realized she was moving from teen to full-on adult.
TLC
TLC wasn't the first to wear all-matching outfits as part of their group's "thing," but they were some of the best at it. Considering the absolutely wild crop tops on display (and Lisa's hair!), I actually appreciate that their makeup is fairly mellow and low-key.
Cyndi Lauper
Cyndi Lauper had maximalist style that every '80s girl wanted to emulate. Taking a lot of very striking elements—dark lip, dark brows, dark eyeshadow, and a messy teased pixie that's going in every direction—Lauper nevertheless looks incredibly cohesive.
Megan Thee Stallion
First, I just really love Megan Thee Stallion's choker, and it makes sense that she would style the look around the statement piece. Second, the impressive contouring and dramatic eye makeup absolutely complements the necklace and the boning on her dress.
Pamela Anderson
My '90s queen, Pamela Anderson was in full force here, with her long platinum blonde hair, her pink frosted lips, and her dramatic black eye makeup. Bonus '90s points for that choker (and the fact that she's making thin eyebrows look better than the rest of us).
Cher
Technically, this is an afterparty post-VMAs, but Cher looks so stunning here that I have to add it to this list. The blonde pixie (with brows dyed to match), the lavender eyeshadow, the completely nude lips, the statement earrings and headband—it's all brilliant.
Shakira
An important part of Shakira's trademark style has been her long, voluminous hair (I have always wanted mine to look like hers—alas). Here, the highlights and long layers give depth and volume, which means she can keep her makeup simple and complementary.
Rihanna
Rihanna's whole career has been deeply stylish, and she's always brought her makeup and hair into the look (she was a makeup expert long before she launched Fenty!). This combo of pixie, bold eyelashes, and red lip make her look like a '50s-era aesthetic got a modern refresh.
Jennifer Lopez
Similarly, J. Lo has had iconic style and beauty looks for a long time. This was one of her early appearances at the VMAs (2000, to be exact), and this all is extremely on-brand for a Y2K aesthetic. I appreciate how neutral her makeup is, so that she still comes off as understated.
Courtney Love
In a legendary red carpet appearance, with partner Kurt Cobain and their baby in tow (they were literally holding a bottle), I must admit that Courtney Love looks great here. The red lip and soft waves in her platinum hair look very classic—a surprise, given her edgy persona.
Iman
Iman is a vision here in that floral dress (David Bowie looks appropriately enthusiastic to be her date). That deep wine-colored lip gloss is utter perfection, and when paired with a similarly hued eyeshadow, the model is doing bold and dramatic without overselling it.
Lady Gaga
While everyone (appropriately) was focused on the literal meat dress Lady Gaga was wearing, I actually think her makeup looks really great here. And, in a matching moment I didn't realize until this very moment, her red lipstick matches the meat on her head.
Cindy Crawford
Cindy Crawford in belted Versace figuratively shut down the red carpet (it was more unusual than it is now to see such a startling design), but I like how her makeup and hair are appropriate over-the-top but still subtle and matte. Not fighting with the outfit, but equally striking.
Beyonce
To announce to the world that you're pregnant, why not do it mid-performance at a major awards show?? I'm so impressed by the softness here: gentle blonde waves, nude lip, deep gray eyeshadow, all in contrast to the sequined perfection of her outfit.
Britney Spears
If you're going to wear a snake as an accessory, your beauty look had better bring it, that's all I'm saying. Britney Spears is giving us some great wavy hair and pink lip gloss, but (as ever) I'm drawn to the very '00s glitter highlighter she has on her cheeks.
Madonna
It's hard to outdo the Queen of Pop! When Madonna took to the VMAs stage singing "Like a Virgin" in a wedding dress and a "Boy Toy" belt, we were forever changed. And that red lip and messy, crunchy curls will live in infamy as an indelible part of this iconic look.
