Rihanna's Red Carpet Beauty Evolution, From 2005 To Today

Riri hit up the VMAs for the first time in August 2005 looking sparkly, this time with her hair pulled back with a few piece-y bangs swept to the side. Her eyes were rimmed with eyeliner with just a touch of copper along the lower lash line. The lipstick was giving mid-2000s frost in the best way. No one knew at the time, but Rihanna would go on to attend every MTV VMA red carpet from there on out.

In November 2006, the singer rolled up to the 13th annual MTV Europe Music Awards in Copenhagen, Denmark with black ringlets, glossy lips, and massive eyelashes. This is when Rihanna began to step away from all things pink and sparkly and into her fashion era.

Rihanna attended the American Music Awards for the first time in 2007, where she scooped up an award for Favorite Female Artist — Soul/R&B and then graced the world with a performance of “Umbrella” (ella, ella...). On the red carpet, the singer showed off her gritty rocker side with short hair, leather gloves, and a smoky eye.

During her Good Girl Gone Bad era, Riri stepped out with a side-swept pixie, which was created by the singer’s go-to hairstylist Ursula Stephen. The two went for an extra-chic look on purpose, hoping to set Rihanna apart from other R&B singers who often wore long, wavy locks.

Here, at the 2008 MTV Video Music Awards in Los Angeles, Riri secured her spot as one of the edgiest stars to walk the red carpet. She was still rocking her pixie, this time with a streak of bleached blonde in the middle. For her makeup, Riri played up her eyes with smudgy eyeliner, then casually turned the camera people to stone with a single glance.

In November 2009, Rihanna arrived at the American Music Awards and turned heads on the red carpet with blonde hair and her signature cat eye — and then went onstage and performed "Mad House," "Wait Your Turn,” and "Hard." Casual.

Rihanna had yet another iconic beauty moment at the Grammy Awards in January 2010. Her Elie Saab dress was angelic yet fierce, so she wore makeup to match. The eyeshadow? Blue, sparkly, and icy. The lips? Glossy AF. The nails? Manicured to the heavens.

At the 2010 American Music Awards, Rihanna went all red: She served up red ringlets, a red lace dress, and pinky makeup for an overall cohesive look. After photographs snapped pics of her ‘fit in front of the Nokia Theater in Los Angeles, she went inside to perform and snag more awards — as she does.

In one of her most memorable red carpet moments, Rihanna broke the internet in a see-through Jean Paul Gaultier gown and a bright red lob at the 2011 Grammys. While her makeup artists usually bring attention to her eyes, this time it was all about a dark, vampy lip.

In 2011, Rihanna launched her very first fragrance: Reb'l Fleur. At a launch event in London, she went for a mermaid goddess look complete with big, side-swept curls, rosy cheeks, and a neutral lip to complement her teal, feathered dress.

Rihanna has become a staple at Met Gala over the years, first attending in 2007 for the theme “Poiret: King of Fashion” where she wore a white gown, smoky eye, and an angled bob. Four years later she attended the “Alexander McQueen: Savage Beauty” event whilst rocking the most stunning red braid, wine-colored lip, and smoky eye. The green earrings added a gorgeous contrast.

To play off the simplicity of her Giorgio Armani gown — a sleek little number she wore to the 2012 Grammy Awards — Rihanna went for shaggy blonde waves, simple jewelry, and a slick of sultry eyeliner. It wouldn’t be a Rihanna red carpet without that eyeliner.

At the 2013 Grammy Awards, everyone’s fave girlie showed up to the red carpet in one of her most wearable yet still totally stunning makeup looks yet. The brows were arched, the eyeliner was serving, and she tied it all together with a fire engine red lip and matching nails. For a finishing touch, she brought back her long golden waves.

For a photo call ahead of the Chanel Haute Couture Fall-Winter 2013/2014 show in Paris, Rihanna graced us with pearls, pearls, and more pearls, as well as a glimpse at her infamous tattoo — one of many tats the singer has collected over the years. In keeping with Chanel’s understated style, the singer kept her makeup simple and showed off her ombre-style highlights.

For her sixth red carpet walk at the AMAs, Rihanna went back to her roots with a sultry black pixie, neutral lip, and signature black eyeliner. While Riri clearly possesses the power to rock any look, she has continually returned to this glam-meets-goth style.

For the “Charles James: Beyond Fashion" Costume Institute Gala at the Metropolitan Museum of Art in May 2014, Rihanna piled her dark hair atop her head for a voluminous updo. She kept her makeup simple, so all eyes were on the two-piece Stella McCartney gown.

To ensure she shined bright like a diamond, Rihanna wore a bedazzled hair scarf and matching sparkly naked dress to the 2014 CFDA Fashion Awards — a night where everyone’s expected to stun. The hair scarf brought all the attention to her eyes, which were as smoky as ever with a dusting of frosty glimmer on her lids.

It’s tough to spot her simple monochromatic makeup amongst the pink plumes of this Giambattista Valli gown, but perhaps that’s the point. Rihanna has never been afraid to go for a muted look so her ensemble can be on full display. Regardless, all eyes were on her at the 2015 Grammys.

In one of her most memorable red carpet moments, Rihanna walked the carpet at the 2015 Met Gala in a mile-long Guo Pei gown, intricate headpiece, and layers of gold necklaces. Her makeup artist, Mylah Morales, went for blunt brows and pink eyeshadow and ultimately created a look we hadn’t seen before. The auburn, flipped bob brought it all together.

The recording artist flipped the script when she hosted the 2nd Annual Diamond Ball, where she rubbed elbows with Kylie Jenner and Emily Ratajkowski on the red carpet. Instead of her go-to pixie, Rihanna went for extra-long black tresses that were slicked back and straight. Her shimmering highlighter matched her silky ensemble.

Always one to switch things up, Rihanna went back to the short hair club for the 2016 BRIT Awards in London, England. She paired her sleek bob with the most stunning lavender eyeshadow, which was accentuated with a slick of black eyeliner, bronzed cheekbones, and a baby pink lip.

Rihanna strolled the red carpet at the 2016 Billboard Music Awards with a bob, bangs, and simple, everyday makeup. It went perfectly with her olive shirt dress and minimal jewelry. But don’t worry — she quickly changed into a stage-worthy look and brought the house down with a rendition of Anti ballad “Love on the Brain”.

Take a deep breath before you gaze upon Rihanna’s 2017 Met Gala look, for it is truly stunning. To fit the “Rei Kawakubo/Comme des Garcons: Art Of The In-Between” costume theme — and her Comme des Garçons dress — the star went with a top knot, blunt bang, and wash of ’80s-style draped pink blush that blended right into her pink eyeshadow. The fuchsia creation was the brainchild of makeup artist Lora Arellano.

Remember when tiny sunglasses were a thing? Rihanna was on that train in 2017 when she strutted the red carpet at the 70th Annual Cannes Film Festival, specifically for a screening of the movie Okja. Behind the shades you can spot metallic copper eyeshadow — one of her faves — and perfectly sculpted brows.

The singer was all over red carpets in 2017 when she launched her now wildly successful makeup brand, Fenty Beauty by Rihanna, a shade-inclusive line that works for all skin types. Here, she wears a hot pink lip and smoky eye outside the Callao cinema in Madrid, Spain — which truly stunned.

In April 2018 Rihanna attended the Sephora Loves Fenty Beauty by Rihanna launch event in Milan, Italy. Here, she’s rocking a more classic old Hollywood glam: a bold red lip, lengthy waves, and butterfly-like eyelashes. Of course, since it’s Rihanna, she made it her own with a dusting of gold shimmer across her lids.

While arriving at The Fashion Awards in London, England, Rihanna paused on the red carpet to show off her braided hair, sleek makeup, and mint green Fenty dress that she wore with gloves, a shawl, and a choker necklace. It was giving coolest-girl-on-her-way-to-prom.

The 2021 Met Gala theme was “In America: A Lexicon of Fashion” — and it inspired one of the singer’s most eclectic looks yet. A diamond headpiece peeked out from under a simple black beanie, while her dress collar rose up behind her ears to frame her goth-chic plum and lavender makeup, created by Fenty Beauty’s global makeup artist, Hector Espinal. Before applying all that gorgeous color, Espinal used the Fenty Skin line to cleanse, tone, and hydrate Rihanna’s face.

As she awaited the arrival of her first baby with boyfriend A$AP Rocky, Rihanna was still hitting up events and doing the most (as she does). In March 2022, she was spotted outside the Dior show during Paris Fashion Week looking dark and dramatic with half-up hair, tons of lace, and soft goth makeup.

In October 2022, Rihanna attended the premiere of Marvel’s Black Panther 2: Wakanda Forever with A$AP Rocky. Even though their baby had arrived only five months earlier, Rihanna was looking as diva as ever with lengthy waves, braids, and a perfect ’90s-era lined lip.

To kick off 2023, Rihanna turned it out at the 80th Annual Golden Globe Awards. She put a twist on 1950s glam by quite literally twisting her hair into an intricate updo. Her makeup was done by Priscilla Ono, who was assisted by Yvette Evora, both of which gave her a stunning monochromatic glam in the most gorgeous dusty pink hue.

Rihanna's makeup artist Priscilla Ono glammed the singer up for the moments leading up to her performance at the Super Bowl halftime show — which was quite literally show-stopping, to say the least. Halfway through the act, Rihanna even touched up her own makeup with a quick pat of Fenty Beauty Invisimatte Instant Setting + Blotting Powder. And this was how she debuted her just-launched velvet icon lipstick in the shade ‘the MVP’.

In March, Rihanna attended the 95th Annual Academy Awards with a perfect top knot, bronzed highlighter, and red lip — more of Ono’s handiwork. The lipstick in question? Fenty Beauty’s Fenty Icon Refillable Lipstick in Grill Mast'r. While she’s currently expecting her second child, there’s no stopping this beauty icon.