The fearless beauty chameleon and comic on "taking her power back" when it comes to her hair, her collection of wigs, and living without regret.

Phoebe Robinson
Credit: Carolina Herrera dress. Anthony Maule/WYO Artists.

When I think of a beauty chameleon, I think of someone like Madonna or Rihanna. I certainly don’t think of myself. I’m a comedian, so I’m never like, “I feel like a beautiful babe!” It’s like, “What? Stop it. You’re a joke!”

As a kid, I felt a lot of pressure for my hair to look perfect. I would see women like Tyra Banks, Halle Berry, Naomi Campbell, Erykah Badu, and Lisa Bonet and think, “I wish I looked like you guys.” In the black community you’re so heavily judged on your hair always looking on point. So when I was growing up in the Midwest, my mom and I would go to the salon about every six weeks to get our hair permed or relaxed. It was tradition, and when we got there every other black lady in the community was there getting her hair done too. They would put this really creamy substance — which we called creamy crack — on your hair. If you left it on for too long, you’d be in a lot of pain. After it was rinsed out, it would keep your hair straight. My mom paid so much money for it that I knew I couldn’t mess it up. I literally kept an umbrella with me at all times in case it rained. I was always running from the rain. I tried not to sweat too much, and I wore a sleeping cap to bed. Between trips to the salon I’d wash my hair, and my mom would use a hot comb to straighten my edges. I had bangs then, and they were not cute. Every night I’d put a roller in my hair to get that perfect bang curl. It looked like a mess.

Eventually, I decided to take the power back. I stopped relaxing my hair after high school and really embraced changing up my look when I moved to New York for college. I wasn’t making the best style choices at the time; I was still dusting off my “Midwest fashion,” aka flared jeans and Steve Madden cowboy boots when my behind had never spent a single day as a ranch hand. I started flipping through all the fashion magazines and realized that beauty is another form of expression. I stopped taking it too seriously and discovered that makeup and hair are places where I can play.

Phoebe Robinson
Credit: Adeam jacket. Jennifer Fisher hoops. Bleecker & Prince ring. Anthony Maule/WYO Artists

My look really depends on my mood. If I feel quirkier one day I’ll express that through beauty. It also depends on what I’m doing [professionally]. When we did Season 2 of 2 Dope Queens, I wanted my looks to be a reflection of the work I had put into the show and to celebrate black culture. I’m probably at my most bare-bones when I’m doing stand-up. That’s when I show off my bubbly, silly side. Whenever I’m writing, I’m just lying around in my apartment [makeup-free]. If I head out for a meeting, I’ve got to be able to put on a face in less than 10 minutes and be out the door. I’m definitely not walking down the street with a bold blue eye! Although I do love a good Fenty lipstick.

No matter what my look is, I’m always still being myself. I don’t have a Sasha Fierce [what Beyoncé called her onstage persona] or anything. It’s just that sometimes I want to have red hair and look like a Nordstrom Rack Janet Jackson, so let’s do red hair! I try to bring a sense of lightness and positivity to everything I do. I’m not feeling straight hair every day, and I’m not feeling cornrows every day either. If I’m going on vacation and want to have a Zoë Kravitz braid moment, then that’s what I’m going to do. I like to push my own boundaries and show off different sides of my personality while I’m at it.

That’s where my wigs come in. I have about 10 at this point, and I’ve named almost all of them. I mainly rotate between five or six styles. There’s Chaka — named after Chaka Khan — which is big and curly with a cute bang. I always pack Chaka when I’m traveling, just in case I want to have a cute wig moment when I’m on the road. I have a bone-straight one called Naomi, after Naomi Campbell. I have a little short pixie that’s named Toni for Toni Braxton. Then I have a Cleopatra-like bob and a really long, wavy style that I wear when I want to feel like a young 27. I also have a giant ’fro that doesn’t have a name. It’s powerful enough that it doesn’t need one.

Culturally speaking, I think we’re in a great moment when black [women’s] hair is being celebrated in all its different permutations. Straight relaxed hair is no longer the only kind of black beauty, which is awesome. I hope the next generation of black girls — or any women with tight coils on their head — feel like they can do great stuff with their hair and look beautiful. Despite social media’s problems, there are so many hair and makeup tutorials now. Seeing everyday people show you how to replicate a look in real life makes you feel more confident and empowered to try something different. People are pushing each other to do really cool things, and so much information is being shared. It would have been nice to have had that when I was in high school.

Phoebe Robinson
Credit: Oscar de la Renta blouse. Anthony Maule/WYO Artists

Still, there’s a lot of illusion in today’s world. Many of the images out there aren’t real. Nobody looks the way they appear to look in magazines and on sosh meeds and if you beat yourself up because of the illusion, you’ll feel inferior. Don’t let negativity take up unnecessary space in your brain. Just highlight what you like about yourself, whether it’s a dope gap in your teeth or big lips. Show it off! Then that confidence will spread to all your other parts.

Don’t get me wrong: There are still times when I assume something won’t work on me before I even give it a shot. But my hair and makeup people — shout-out to Sabrina Rowe and Delina Medhin — encourage me to try it. They bring me ideas before an event, or I’ll text them being like, “Oh, I saw that Beyoncé did this — can my low-budget ass try it?” It’s a team effort, and when you’re working with such creative people, you don’t want to keep doing the same thing. You want to give them the chance to express their creativity, so we always try to keep things fresh.

I know it sounds so annoying to say, “I try not to live with regret,” but I really don’t have any regrets, especially when it comes to beauty. So many looks I wear are going to be out of style for most of the time that I’m alive. Even if something is ridiculous when I look back on it (my I Heart NY T-shirt that I purchased and wore unironically when I first moved to N.Y.C. is a particularly charming lowlight), it’s still a cute snapshot of my life. That’s who I was then, and I thought I had a great look going! Sure, time has told me it’s not a great look. But if I can’t change it, I don’t want to regret it.

Instead, I focus on the joy of it all. This isn’t life and death. If I’m being a sourpuss when I do my hair and makeup, then I’m just going to ruin it for myself. I’m only going to look this way for a short period of time, and I don’t want to be in my 70s or 80s and think, “Oh, I wish I would’ve appreciated how I looked when I was younger and had more fun with it.” So I try to be present and positive. And then I just go for it.

Robinson is currently on her stand-up tour, Sorry, Harriet Tubman. Her next project is an interview-based series that will air on Comedy Central in 2020.

For more stories like this, pick up the October issue of InStyle, available on newsstands, on Amazon, and for digital download Sept. 20.