12 Hairstyles From The 1990s VMAs That Deserve A Moonman

They’re totally award-worthy.

by Hilary Shepherd
For the VMAs red carpet, Lil Kim's purple wig was one of the most memorable hairstyles.
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Since they first began back in 1984, the MTV Video Music Awards, aka the VMAs, have given way to so many incredible moments, from performances (no one will ever forget Britney and her boa) and on-stage occurrences (cc: Kanye West) to head-turning (and sometimes head-scratching) fashion and beauty looks. You never know what to expect when celebs hit the VMAs red carpet — and that’s exactly what makes the show so exciting to watch.

While there’s certainly been no shortage of memorable years over the past several decades, the 1990s arguably stand out as one of the top eras for all things iconic, especially on the hair and makeup front. Think about it: There’s a reason why contemporary stars like Bella Hadid, Keke Palmer, Teyana Taylor, Olivia Rodrigo, and more have recently pulled hair inspo from the time period.

With the 2021 VMAs slated for Sunday, September 12, it’s only fitting to take a peek through the show’s ‘90s archives, when braids, floral accessories, and space buns reigned supreme on the red carpet. Below, revisit some of the greatest hits while you wait for Sunday’s big show. Here are 12 of the best hairstyles from the VMAs during the 1990s.


Mariah Carey’s Retro Waves

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Mariah Carey’s black, two-piece outfit she wore to the VMAs in 1997 was a total show-stopper, but her retro, Old Hollywood-esque waves and deep side part became instantly memorable. Though the crooner didn’t receive a Moonman that year (she even recently poked fun at herself for not winning anything), her hair was totally award-worthy.


Sinéad O'Connor’s Buzzcut

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Sinéad O'Connor tied with Madonna for the most awards received (three, to be exact) in 1990, the year she released the seminal track “Nothing Compares 2 U.” Though the music video — and the song’s heartbreaking lyrics, written by Prince — became classic, it was O’Connor’s buzzcut that garnered attention.


Drew Barrymore’s Daisy Clips

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Everything about Drew Barrymore’s VMAs aesthetic in 1995 was quintessentially ‘90s: the dark lipstick, pencil-thin brows, and, of course, the sweet daisy clips that adorned her curly blonde bob. Considering hair clips (and daisies) are back on the scene, it’s safe to say Barrymore was way ahead of her time with this look.


Gwen Stefani’s Space Buns

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Before making her debut as a solo artist in 2004, Gwen Stefani stood out as the eccentric vocalist from No Doubt. In 1998, Stefani attended the VMAs with her former bandmates sporting a furry bikini top in an icy blue color that matched her strands. With space buns and face jewelry, the singer looked totally otherworldly.


Madonna’s Marie Antoinette-Inspired Updo

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Madonna has served up *tons* of amazing beauty looks throughout her career, but it was her jaw-dropping performance at the VMAs in 1990 that really took the cake. Clad in Marie Antoinette-inspired garb, the star performed her hit “Vogue” sporting feathered hair accessories and ringlets reminiscent of the queen of France. Iconique.


Lisa “Left Eye” Lopes’ Triple Threat

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Lisa “Left Eye” Lopes’ hairstyle was just as futuristic (and cool) as the get-ups TLC sported to perform “No Scrubs” at the VMAs in 1999. With streaks of red throughout, the former singer, who tragically passed in 2002, separated her hair into three parts with strands of hair intentionally falling out of each one.


Lil’ Kim’s Lavender Locks

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Arguably one of the best VMAs looks of all time, Lil’ Kim resembled a stunning mermaid when she hit the red carpet in 1999 wearing an off-the-shoulder, lilac-colored jumpsuit (and a seashell-shaped pasty) and a matching purple wig. Unforgettable, fun, and replicated. 10/10.


Brandy’s Half-Up Micro Braids

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Brandy performed the evergreen hit “The Boy Is Mine” alongside fellow artist Monica at the VMAs in 1998. The song was nominated for two awards — Best R&B Video and Video of the Year — but ultimately didn’t win the silver statue. Brandy’s hairstyle, however, was a winner: Half-up and half-down, the micro-braided look was peak ‘90s. Here for it.


Cindy Crawford’s Tousled Strands

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Another amazing half-up, half-down hairstyle belonged to Cindy Crawford. In 1992, the supermodel paired her BDSM-inspired Versace gown with a simple yet sultry hairstyle. The top half had a little extra volume, while her lower strands looked freshly brushed out and natural.


Janet Jackson’s Understated Braids

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Janet Jackson did normcore before the term was invented. Case in point: The casual denim overalls and baseball cap she wore to the VMAs in 1994. Though her aesthetic was decidedly low-key, Jackson didn’t skimp on makeup and hair, sporting blue liner, red lips, and braids reminiscent of her character’s plaits in the 1993 film Poetic Justice.


Prince’s Blue Accessories

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In 1999, Prince introduced TLC at the VMAs wearing an amazing blue jumpsuit, larger-than-life hoop earrings, and braids with matching blue beads. It’s hard to nail down the legend’s most stellar looks at the VMAs (remember his cheeky yellow suit?), but this monochromatic look was definitely one to remember.


Britney Spears’ Super Straight Locks

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Britney Spears made a case for the flat iron with the stick-straight strands she rocked at the VMAs in 1999 (her first VMAs performance ever!). With choppy layers and a very Gen Z-friendly side part, Spears’ look was simple and sleek.