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It takes a village to prep someone for the red carpet. Okay, maybe not that much, but if an event that requires putting yourself on display to thousands, if not millions, is on the schedule, reinforcements are required. And for Tinseltown’s most-talked-about red carpet stars, that means calling in the best of the best in hair and makeup.

More often than not, celebrities form bonds with their glam squad that go beyond “work;” they become friends or unofficial family members who just get “it.” Not only do they know how to create hairstyles or makeup beats that turn heads; these looks do an incredible job of reflecting the spirit of whoever is wearing it. And in an era where women are stepping up and speaking out more than ever, we’re glad to see this famous beauties like Kristen Stewart, Lupita Nyong’o and more for reminding us that hair and makeup are a means of a self-expression; a way to celebrate our respective cultures, creativity, inner spirit, and whatever else we so desire.

Ahead are nine of today’s most talked-about stylist and celeb duos, some of whom tell us what makes their muses true-blue beauty risk-takers.

STYLECASTER | Hollywood's Boldest Beauties | Kristen Stewart

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The Makeup Artist: Beau Nelson

The Bold Beauty: Kristen Stewart

I’ve worked with Kristen for over 10 years now, I think. We started working together during the press for the second installment of the Twilight series. We have a really intuitive, easy relationship. I think after this long, we have a trust between us that sort of allows us an unspoken vibe… we just know what to do. It definitely is always a collaboration with the entire team. Hair and styling play a big role and it’s important that everything goes together and looks cohesive. I most often take my inspiration from the clothing.

Kristen is up for anything. She can carry a look because she’s comfortable with herself… To me, the makeup never wears her. She wears the makeup with confidence and power, making it seem like it’s just part of her face. I think the key to wearing any look, bold or otherwise is confidence, and Kristen is a strong, confident, powerful woman.  

One of my favorites actually is from when we were in NY for a film screening and she wore Rodarte. I did a beautiful unexpected pink look on her with blush that came off her eyes and onto the temples and cheekbones. I loved how feminine and soft it was while being quite radical and strong.

STYLECASTER | Hollywood's Boldest Beauties | Lupita Nyong'o

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The Hairstylist: Vernon Francois

The Bold Beauty: Lupita Nyong’o

Lupita and I started working together on the press tour of ’12 Years a Slave’ in London. We quickly knew that we’d become friends, and we did. We’ve worked together ever since.

We always collaborate creatively on her hairstyle, which will often be inspired by what she’s wearing.  All elements of her overall look must work together too, so, accessories, dress, shoes, make-up and hair complement each other. We are a team. Together we design and then I will execute the hairstyle. Sometimes Lupita will have a vision and it’s my role to bring that vision to life in the most honest way I can.

Lupita is a risk taker because she operates from an authentic space and is often keen to lean into the unknown. There are no boundaries when it comes to exploring greatness.

I would have to say, one of my many favorite hairstyles I’ve done for Lupita is at the Met Ball in 2016. This hairstyle really provoked conversations as to what is acceptable on the red carpet for women with Afro hair and women of color. The internet went crazy because for the first time, at the Met Ball at least, there was this beautiful black woman on the red carpet celebrating her heritage in the most respectful way with a modern twist. It was delightful to watch. It made people talk. It made us ask the question: what is beautiful hair?

STYLECASTER | Hollywood's Boldest Beauties | Zendaya

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The Hairstylist: Ursula Stephen

The Bold Beauty: Zendaya

I started working with Zendaya at the Met Ball in 2016. I got a last minute call to do her, and since then, we have worked together consistently.

Our working relationship is pretty laidback. She is a “no fuss” kind of girl, who carries a very calm energy. Her looks are always led by fashion. When it comes to collaborating and inspiration, her styling team usually has a vision of what they want her look to be, and I’m in charge of interpreting and bringing that vision to life in her hair.

Zendaya is a beauty risk taker because she doesn’t take herself too seriously and totally gets this fashion thing. It’s always a great time transforming her!

To date, my favorite and most memorable look I’ve done on Zendaya is the red textured bob we did for the Met Ball this year. I first prepped her hair by applying Suave Professionals Avocado & Olive Oil Smoothing Leave-In Conditioning Cream in her natural hair before blowing it out straight. The look was totally outside the box, but still fell perfectly in-line with the theme of the gala, which separated her from the other attendees. The interpretation was original and came with lots of significance and represented the climate we are In today – the strength of a woman!

Cardi B.

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The Makeup Artist: Erika La Pearl

The Bold Beauty: Cardi B.

Cardi B. and I started working together about 3 years ago. She came to Atlanta for an event and the rest is history. I really enjoy working with her. She is very easy to work with. She’s so sweet, funny and knows what she likes. What I love about her is that she allows me to be very creative with her makeup. What I try to do is coordinate her makeup styles with her out outfit or with how she will wear her hair. Cardi B. loves a good cat eye, so she doesn’t care what I do as long, as I do that wing cat eye on her.

What has given her staying power is that she goes beyond people’s expectations and she’s not afraid to try new looks. My most memorable looks are the Coachella look, The ‘I Like It’ music video look, and of course the Met Gala!!!

The Met Gala especially, because it is one of the most prestigious events and I wanted to show off her beauty along with the gorgeous dress! For Coachella, I wanted to make her eyes pop with the rhinestones because it worked well with the whole look. In addition, it is nice to see other inspiring makeup artists and beauty YouTubers recreating these looks and going viral!

Rihanna

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The Makeup Artist: Priscilla Ono

The Bold Beauty: Rihanna

Our favorite “good girl gone bad” really needs no explanation. Ever since she chopped off her hair and dyed it black over a decade ago, the singer, actress, and beauty boss has continued to set trends on and off the red carpet. And with the launch of her wildly successful company Fenty Beauty, the 30-year-old has zeroed in on not only creating more inclusive makeup, but creating new ways to wear it, too.

Ono, who also worked with Amber Rose, is responsible for all of Rihanna’s #fentyfaces thus far, and although the makeup pro’s got the skills needed to collaborate with one of Hollywood’s biggest beauty icons, she’s still learning some unexpected tricks. In an interview with E! Online, she revealed:

“Usually, as makeup artists, we use small buffing brushes to do our eye shadow or we are really precise with whatever we do, but with Rihanna, there’s no limit. She likes her eye shadow to be put on with our cheek-hugging brush sometimes. She wants it to look like a wash of color…We never really take risks and use brighter colors, but with Rihanna, you know, we like to bend the rules.”

Katy Perry

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The Hairstylist: Rick Henry

The Bold Beauty: Katy Perry

Katy’s signature hair color has long been black, but when she chopped it all off in mid-2017, the singer decided to give her multi-colored wigs a break and dye her real strands instead. Not long after getting comfortable in a platinum-blonde pixie, the new TV host began experimenting with a slew of hues, including bubblegum pink, which she wore on “American Idol,” this past April. Henry, who also counts Brittany Snow and Jessie James Decker as clients, most recently dyed her hair a vibrant purple. In an interview with Byrdie, she elaborated on her haircut, saying:

The biggest experiment I’ve done is cutting off all my hair. Now I can’t hide behind it. I wanted to know that I could still feel beautiful and love myself without it. It’s fun, it’s freeing, it’s liberating, and I don’t think that ‘sexiness’ and ‘femininity’ is just one thing—long hair. I suppose the goal is to redefine what femininity means to me. I like to throw that kind of curveball into whatever traditional beauty is.

Issa Rae

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The Hairstylist: Felicia Leatherwood

The Bold Beauty: Issa Rae

As Hollywood’s premiere natural hairstylist, Leatherwood has gifted us with enough inspo for all textures; from the loosest waves to the kinkiest curls. Although she’s worked with other naturalistas, including Yara Shahidi, her work with the “Insecure” star is the most noteworthy, mainly because her hairstyles are rarely without a unique touch, like these embellished twists, which she wore as a crown to the premiere of “A Wrinkle in Time.” And in an interview with InStyle, the actress and writer explained how college played a huge role in her evolution:

When I was in middle school, I begged my mom to get a relaxer, and my hair fell out. So I was forced to be natural, and I was ashamed. I would wear a hoodie or a scarf to hide my hair. It wasn’t until college that I saw a lot of confident, self-affirming black girls wearing their hair natural on campus, and it was beautiful. I thought to myself, “Why am I ashamed of the hair growing out of my head?”

risk taker zoe kravitz These Are Hollywoods Biggest Beauty Risk Takers

The Makeup Artist: Nikki Nelms

The Bold Beauty: Zoe Kravitz

As one of Hollywood’s most in-demand hairstylists, Nelms is never not busy collaborating with a long list of famous clientele, such as Janelle Monae and Kelly Rowland, but Kravitz is definitely the boldest. Her hairstyles  have included everything from platinum blonde pixie to jet black micro-braids, which she wore to this year’s Met Gala. In an interview with Vogue, the “Big Little Lies” star explained what makes them such a great team:

Nikki’s been doing my hair for a really long time, maybe six years. We met at a photo shoot. She’s not always the one who necessarily braids my hair; I have people who braid my hair all over, depending on where I am. But in terms of figuring out what to do next, she’s been huge with that. She’s has a great, great eye, and she’s incredibly talented. We just connect in terms of a certain aesthetic. When I first got the blonde hair, it felt really thick and intense, and she helped me cut it down and make it a little bit airier and elf-like.

Lady Gaga

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The Hairstylist: Frederic Aspiras

The Bold Beauty: Lady Gaga

Mother Monster doesn’t give us red carpet looks; she delivers red carpet moments. The past decade has been paved with a gang of memorable hair and makeup slays, including a David Bowie-inspired mullet at the Grammys and rhinestone eyes for the Superbowl, but as of late, her hair is truly impressive. Aspiras has been working with the “A Star is Born” actress for years now, but this year’s corseted braid at the Grammy Awards proved to be one of their most talked-about collaborations. And in an interview with Australian Vogue, he explained the inspiration:

“After meeting with the Haus of Gaga team and seeing the dress, I drew up numerous sketches of ideas I had and presented them to Gaga. We tried many different styles but it was the corseted braids that worked perfectly with the gown and make-up,” he said.