Ciara's Beauty Evolution Is All About Experimental Hairstyles & Stunning Makeup

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Picture this: It's 2004 and you're breaking a sweat while dancing to Ciara's iconic song "1, 2 Step" in your room. When you weren't listening to her Goodies album on your stereo, you might have caught a glimpse of the star on MTV's TRL in the early 2000s. While yes, she's best known for her catchy Billboard hits (she has eight top-10 hits, to be exact), Ciara's beauty evolution is also full of can't-miss moments. The celeb is no stranger to experimental hairstyles, which she effortlessly complements with natural glam.

Ciara's successful career quickly took off after the launch of her Goodies album in 2004. Right after her album dropped, she began working with hairstylist Kiyah Wright. "Ciara is definitely a young beauty icon who always aims for sexy, innovative styles that are effortless," Wright, who still works with the musician today, tells TZR. "She definitely isn’t afraid to take risks with her hair." Through their 17-year relationship, the hairstylist has been behind everything from Ciara's long bobs to her wide bangs, but she has a favorite look out of them all. "I absolutely love the long waves I did on her for Jimmy Kimmel [in 2016]," Wright says.

You can also thank César DeLeön Ramîrez (who has been styling the musician's hair and wigs for 12 years now) for some of Ciara's most talked-about hair moments. "It's been a beautiful journey because we have very similar taste when it comes to fashion and style," he notes. The hair expert says Ciara's look is ever evolving, trendsetting, and has generally been aspirational. "I've always believed in playing outside of the box while still making her feel sexy," he says. "It's always been important for us to be ahead of trends rather than following them."

And even before she stepped into the spotlight, the Grammy-winner started collaborating with makeup artist Yolonda Frederick, and still is to this day. "I have been working with Ciara since she was 16 years old," Frederick tells TZR. "I actually did her makeup for her high school prom! We go way back... she's my bestie and my muse all in one beautiful package." Frederick says Ciara's go-to makeup look is what she's coined as natural glam. "Most times it's that sweet and fresh-faced no-makeup, makeup look," she explains. "However, when it's time to serve 'face' I can definitely pull some tricks out of my bag!"

Get ready to see some major throwback photos from the pop icon. Ahead, find Ciara's beauty evolution from the beginning of her career until now.

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Ciara's Beauty Revolution: Billboard Music Awards, 2004

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One of Ciara's first-ever red carpet appearances was at the Billboard Music Awards in 2004. The star arrived with caramel brown hair, heavy eyeliner, and shiny pink lips.

Ciara's Beauty Revolution: MTV's TRL, 2006

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Still fairly new to the music scene, Ciara made an appearance on MTV's TRL in 2006 with light pink lips and eyes, as well as layers in her hair.

Ciara's Beauty Revolution: For Colored Girls Premiere, 2010

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Ahh, who could forget when black liner in the water line was the "It" look. Ciara was fully on board with this dramatic trend back in the day.

Ciara's Beauty Revolution: American Music Awards, 2013

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"Again, I can't express how much I love when we step onto a carpet with a hairstyle that is so unexpected," DeLeön Ramîrez notes. The hairstylist says the length portrays a '90s supermodel. "We literally provoked the '90s trend to submerge," he says. "I really want to bring this look back on her. We will see!"

Ciara's Beauty Revolution: VMAs, 2015

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DeLeön Ramîrez say Ciara's look at the VMAs in 2015 was one of his favorite bobs he's ever cut. "The length was so perfect, the shape was so perfect, and the movement was so playful," he says. "I'm sorry to say, but we were boldly bringing the bob back into style before anyone would dare to wear a bob."

Ciara's Beauty Revolution: Clive Davis Party, 2015

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Wright says she decided to take Ciara's hair to the floor at the Clive Davis Party in 2015. According to the hairstylist, the star's locks were 28 inches, and featured beachy waves with lots of layers.

Ciara's Beauty Revolution: American Music Awards, 2015

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Frederick says the singer's American Music Awards look in 2015 was a classic. "With Ciara's well contoured black eyeliner to Uoma Beauty's matte lip color in Brenda, this makeup is flawless," she says. "This makeup choice added the right amount of drama to this unforgettable red carpet look."

Ciara's Beauty Revolution: Met Gala, 2016

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"Met Gala 2016 with its futuristic vibe was a fun look," Frederick says. "The Maus x Machina inspired elements illustrated in the hairstyle and wardrobe needed no competition." Therefore, the makeup artist decided to balance the look with a defined smoky eye using Danessa Myricks' Waterproof Cream Primary Palette set with a matte black shadow.

Ciara's Beauty Revolution: Harper's Bazaar Event, 2017

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"This was Ciara’s return of the blonde," Wright says. "We play a lot with color, and when Ciara is pregnant she tends to like to go with lighter hair, so with this style we went with a side swoop, super sexy with a round brushed feel, giving off an effortless style with dark roots and icy blonde highlights."

Ciara's Beauty Revolution: American Music Awards 2018

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Frederick says the makeup she created for the American Music Awards in 2018 was one of her go-to looks for Ciara. Her approach? "A soft ombrè eye with a sprinkle of light in the inner corners topped off with a pinky nude lip like Kylie Cosmetics' KoKo K stunning lipgloss gets us to perfection every time."

"This wig actually shrinks to a shorter length because of the coil texture, but when I styled it I would slightly blow-dry it to stretch the length," DeLeön Ramîrez notes. "I also highlighted this wig to give her an overall neutral, warm caramel moment."

Ciara's Beauty Revolution: Black Girls Rock, 2018

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"Black Girls Rock was Ciara going back dark after she was light for awhile, so we went with a shorter look this time with a little edge," Wright explains.

Ciara's Beauty Revolution: Oscars, 2018

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"We were thinking sexy vibes for the night, so we went with the side swoop using a large barrel curling iron and round brush, and added some soft, caramel highlights to achieve this sexy, sultry off-the-shoulder moment," Wright notes.

Ciara's Beauty Revolution: ACE Awards 2019

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Ciara's beauty at the ACE Awards in 2019 was by far one of DeLeön Ramîrez's favorite looks ever done. "This was a short wig I made for her," he explains. "It's so challenging to make a short wig look so natural, but she sold this look. It also really completed the dress and accentuated her beautiful facial features." For her makeup, Frederick used MAC's iconic Ruby Woo shade on her lips.

Ciara's Beauty Revolution: Met Gala, 2019

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"OK, this right here was the mother of all afros," DeLeön Ramîrez says. "We broke the internet with this one." The hairstylist achieved the look by using six (!) afro wigs combined into one. "I was so proud of how it turned out and at how well she wore it because it was super heavy! I'm still amazed at her strength."

Ciara's Beauty Revolution: American Music Awards, 2020

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Frederick achieved Ciara's luminous makeup at the AMAs in 2020 using MAC's Mineralized Skinfinish in Dark Deep, which she says is the perfect complement to the celeb's caramel skin tone. "This makeup, with its glossy nude lip, connects all the elements of this look, giving it the perfect balance," the makeup artist says.

Ciara's Beauty Revolution: Blue Wig, 2020

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"I colored this wig blue as an idea for a gender reveal when she was pregnant with her last baby Win," DeLeön Ramîrez says. "I love the icy blue tone on her skin. It's fun."

Ciara's Beauty Revolution: Glamorous '60s Look, 2020

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For the Disney Christmas Singalong in 2020, Ciara's whole beauty was inspired by early '60s style. "I wanted a sweeter version of the winged top liner coupled with a cool-toned lippy like Chateau by HIGHR that is indicative of that time period." And Wright says she gave the star a long wide bang with a ponytail for a '60s type of feel.