How I Turned My Biggest Insecurity Into My Power Source

I used to hate them; now it’s the first thing people notice.

Squiggly Line
For some, a lipstick is just a lipstick. But for others, it's a source of strength, creativity, and expression. In our series Power Faces, we'll explore the relationship between strong women and the makeup they choose to wear — or not. Our second subject, Jaraé Holieway, is a stylist, model, and artist living in New York City.
In New York City, everyone wears black, white, or neutral. I’ll be on the subway in a head-to-toe orange outfit and people will freak out — it’s like they’ve never seen a color before. When I moved here from Los Angeles, people told me that by the end of the year, my whole wardrobe would be black. But I’m like, No, I want to bring color to New York.
When I pick a color to wear for the day, it all depends on my mood. Blue doesn’t necessarily mean I’m sad — I think of it as a very royal color. Pink is playful. And red is my signature. Wearing red makes me feel strong, important, and sexy all at once. I just want to wear it all the time. I want to wear it on my face, I want to wear it on my head, I want to wear it on my feet… That’s where the monochromatic thing really started.
I feel like when I walk into a room and I'm wearing all yellow, the happiness and confidence that I have radiates on to other people and they respond to it. Or they just look at me like I’m crazy…
Red Alert
Growing up, my great-grandmothers always wore lipstick — even if they were just going out to the grocery store. Now, it’s a lot more relaxed, but I feel like some of that classic glamour is lost on people. So I'll throw on some lipstick and go to the laundromat. You can be wearing sweatpants and it just gives you that confidence and makes you feel a little extra.
Lipstick for me is a way to stand out and be bold, but I also feel like it's a way for me to say, I'm very empowered. Don't mess with me. Back up. I want to have this sophisticated and soft feeling about me, but at the same time, I want to look like I can kick your butt if I needed to.
Red lipstick is such a classic look and can be very elegant, but on other side of the spectrum, it’s something that’s very fierce and bold. That's what I love about it. When I see other women on the street wearing it, I get really excited. It could be wintertime and no one's out, but you’re fabulous and you’re killing it with your red lip on, and I’m like, Girl, I understand why you're wearing that. It makes me happy to know that she’s probably feeling her best self.
Photographed by Tory Rust.
I feel like a lot of people, especially guys, are confused when it comes to why women wear makeup because they think we're putting it on for them. But no, we're putting it on for us. They’ll say, “You don’t need to wear makeup.” But this is me. This is what makes me feel beautiful — it’s my power.
It sounds really cheesy, but it’s also very therapeutic to sit in the mirror and put my makeup on. It takes time and concentration and that moment is all about me. It’s that additional step of self care every morning that makes me feel good and also makes me look great.
Blank Canvas
I didn’t always used to wear this much makeup — I was a lip balm girl. But in the past few years especially, my relationship with makeup has changed so much. It used to be about trying to hide and cover up my "imperfections." But now it’s about embracing everything I love about myself. And that started when I cut my long hair five years ago.
As a Black woman, a big part of growing up was making sure my hair looked good. It was such a time-consuming process to either get it braided or get it straightened — and I just wanted to be that little girl who went to the pool with her friends. But instead I had to sit in a chair for three hours and I couldn’t go swimming because I just got my hair straightened. I finally got to a point where I was like, I don’t want to do this to myself anymore. I don’t want to hide behind my hair. So I buzzed it all off.
Photographed by Tory Rust.
Immediately, I felt such a sense of empowerment. That thing that had been holding me down and felt like such a weight for so many years had been lifted. And now that I couldn’t hide behind anything, I learned to love myself at its most natural state and my true beauty and who I really am came out.
Fresh Perspective
That's when my relationship with makeup totally changed because I saw it as a way to emphasize the things that I love about myself. I always hated my lips growing up. I'd say, “Why do I have such big lips, Mom? I hate them.” And now I’m like, Wow, they’re beautiful and people pay so much money to have them. Why would I hate them? Now lipstick is such a positive thing, versus something I disliked about myself for so long. I can put a crazy color on my lips and feel great about showing them off and it’s the first thing people notice about me.
Cutting my hair has also allowed me to really emphasize my eyes, too. I never really saw my eyes as beautiful and now that people can see them, they compliment me on them all the time. Now that I have no distraction around my face, it's like a blank canvas. So I paint it and I dress it up. I like to play around with cool eyeshadows and fun liners and dots. It’s about elevating those smaller details. I care less about like it being so perfect or having to look a certain way, just as long as it makes me feel good.
Color Theory
When I started my Instagram account where I post pictures of my bright outfits and makeup and art, I got a lot of messages from people thanking me for the colors on my page and the energy it projects. And that's exactly the reason I do it. It's not always easy. I still don't always feel completely confident and sometimes I do worry about whether this or that angle works because I spent so much of my life disliking the way I look.
But as my following started to build, I realized I had such a powerful tool. The majority of my audience is women of color. Growing up, I didn't have standards of beauty other than seeing girls in magazines who never looked like me. I felt like I never had anyone to look up to. And now, I can put stuff out there that makes people feel good and gives women of color that community.
Photographed by Tory Rust.
I used to feel very confused when I was younger, like I didn't have a place for all the things that I wanted to do. I used to get so many "no's" from people who weren't looking for a model or stylist like me. But I didn't stop. The opportunities are out there and if you have a dream or a passion, now is the time to pursue them, because life is too short to do otherwise.
The fashion and beauty industries are moving in such a positive direction, and it's grown so much in even just the last three years. But I want to see even more diversity in the industry and Instagram has allowed me to further that process in ways I never could have imagined. In the end, if I can use my job as a way to encourage and uplift people to pursue their dreams, then I've done what I set out to do. It's amazing to be able to be a light and role model for other girls who never had anything like this.

More from Beauty

R29 Original Series