Rihanna's Beauty Evolution Is Full Of Unplanned Moments, According To Her Hairstylist

"That's just how we roll."

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You've probably wondered at one point or another, is there anything Rihanna can't do? In short, the answer is no. On top of her highly successful music career, over the past few years, the singer (aka, @badgalriri on IG) has launched her Savage x Fenty fashion brand as well the Fenty makeup and skin care lines. With all the red carpets and fashion shows the musician-turned-designer attends, it's not surprising that Rihanna's beauty evolution is buzzing with glamorous moments.

"She's an open book," Yusef Williams, her longtime hairstylist, tells TZR over the phone. "She'll tell you what she doesn’t like, but she definitely wants to hear what you have to bring to the table. She wants to see how far you can push her." Williams started doing the star's hair after being introduced by her makeup artist Mylah Morales, who began working with her from day one. Morales met Rihanna when she dropped her single Pon De Replay in 2005. "Her makeup aesthetic has always been like let's make her the cool girl to look up to," Morales tells TZR. "It's always been based around fashion, and I wanted to keep her glowy and beautiful, but then edgy at the same time."

When it comes to her hair, Williams says the best looks are the ones that aren't overthought. Yusef recalls Rihanna's hair at the Met Gala in 2014, where they both started pulling pieces out of her bun seconds before heading out the door. "That's just how we roll," he laughs. "When we plan things out, it never works."

Be prepared to see Rihanna's hair and makeup change drastically throughout her career. Below, see her beauty evolution from 2005 until now.

Rihanna's Beauty Evolution: Z100's Jingle Ball, 2005

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When Rihanna was just making a name for herself in the music scene, she arrived at the Z100's Jingle Ball in 2005 with bright turquoise eyeliner in her waterline and long bangs that went past her brows.

Rihanna's Beauty Evolution: Billboard Music Awards, 2006

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"I did a really defined, light smoky-eye," Morales says. "The whole look was really dark." To complete her makeup, Morales opted for an equally bold lip.

Rihanna's Beauty Evolution: VMAs, 2008

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For Rihanna's makeup at the VMAs in 2008, Morales applied a navy eyeliner and a baby pink lip complemented with golden skin.

Rihanna's Beauty Evolution: MTV Europe Music Awards, 2010

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In 2010, Rihanna arrived at the MTV Europe Music Awards with bright red hair and soft pink makeup.

Rihanna's Beauty Evolution: Victoria's Secret Fashion Show, 2012

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"This look came so last-minute," Williams says. He says the goal was to make the hair look like a sculpture, which he achieved by wetting her locks and creating a finger wave. "It's probably one of my favorite looks I've done with her," he notes. As for her makeup, Morales did a vampy burgundy lip with glowy skin and a really clean eye. "All of these looks required lashes," she explains. "I always top it off with a really natural or dramatic lash."

Rihanna's Beauty Evolution: AMAs, 2013

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For Rihanna's makeup at the AMAs in 2013, Morales says she swiped on a really dark kohl eyeliner with a very strong cat-eye and beigy-nude lip.

Rihanna's Beauty Evolution: MTV Movie Awards, 2014

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"That was dreamy," Williams says about Rihanna's hair for the MTV Movie Awards in 2014. "The idea of that was to be super soft, very effortless, and just angelic."

Rihanna's Beauty Evolution: Met Gala, 2014


"It's so funny because we pulled the hair up into a bun and we thought it would look a little too basic," Williams notes. "So I was like, what would Edward Scissorhands do?" Williams and Rihanna grabbed pieces from the bun, which resulted in a whispy, effortless look. "That went from a simple topknot to this sculptured, elaborate topknot."

Rihanna's Beauty Evolution: CFDA Awards, 2014

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"For sure an iconic look," Morales says about Rihanna at the CFDA Awards in 2014. "She was nude practically, so I wanted the focal point to be on the eyes." And for her hair, Williams says she had a super tight bob. "We were basically trying to figure out if the durag was too much," he explains. "So I gave her this super chic finger wave underneath because we were like what if we don't like it. It was super tapered and beautiful. You can see some of the sideburns that swing-out."

Rihanna's Beauty Evolution: Grammy Awards, 2015

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"She wanted to look like a babyface, so [we did] super natural makeup with soft pink cheeks," Morales says. "{It was] almost like a no-makeup, makeup look."

Rihanna's Beauty Evolution: Met Gala, 2015

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Morales says the Met Gala in 2015 was inspired by Asian designers. "The look we were going for was a very extended brow, and, of course, a cat-eye," she says. "Then we wrapped the pink around the eye and the cheeks."

Rihanna's Beauty Evolution: Met Gala, 2017

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"The only thing we could do [with her hair] was to go up because that outfit was [going] sideways, downwards, [and all] around," William says. Therefore, he opted for a tight topknot. "We decided later on to add fringe to soften it up because you know she just looks sweet, like a cupcake. The fringe was the icing on the cake."

Rihanna's Beauty Evolution: Ocean's 8 Premiere, 2018

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"That's my little edgy topknot," Williams says about the bun he did on Rihanna for the Ocean's 8 premiere in 2018. "That's what we call snatching the hair!" To give the look some edge, he pulled out pieces from the bun.

Rihanna's Beauty Evolution: British Fashion Awards, 2019

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Williams says that for Rihanna's hair at the British Awards in 2019, the two wanted to do something soft, pretty, and very youthful. "She looks like a 12-year-old when she braids her hair. This dress was super sexy and really flirty, so I was like we need to go young and fresh. She looked like baby Rihanna that night."

Rihanna's Beauty Evolution: Virtual Fenty Skin Launch Party, 2020

At the virtual Fenty Skin launch party in 2020, Williams decided to pull Rihanna's hair back to show that her products actually work. "This was an homage to my childhood doing my sister's hair," the hairstylist says. As a kid, Williams would play with rubber bands and create fun looks with his sibling's strands.