Inspired by his lifelong love of art and the history behind it, Sir John used his art school education after graduating to land himself a visual merchandising position at Gucci and after a while, started doing makeup alongside one of beauty's greatest makeup artists, Pat McGrath. From there, he parlayed his career in an entirely different direction, combining his passion of art and painting onto entirely different canvas: the faces of Hollywood's elite (Beyoncé, Chrissy Teigen, Viola Davis) and supermodels — like Naomi, Joan, Karlie, Jourdan, and Soo Joo. Five years later, Sir John signed with L'Oréal as a brand ambassador and celebrity makeup artist. Here, his professional insight if this is what you want to do too:
1. You should take an art history class or two. Everything influences beauty, especially art. There have been times that I've been on set and an art director might reference one of Georgia O'Keeffe's paintings, and it's really important to know right then and there what they're talking about. My background in art has definitely helped me truly understand so many references. It's also just really helpful to know how Cleopatra did her cat-eye or what Elizabeth Taylor's looked like, and how they influence today's feline flick.
Artist: Nina Cieminska
2. You have to be ballsy, even when people discourage you. When I first started out, I was backstage and I approached Naomi Campbell at a fashion show. Everyone told me not to talk to her, but I idolized this woman all my life and I was like, "No, I'm going to introduce myself." A week later, she called me to do her makeup and she became my first celebrity client.
3. Instagram is an amazing vehicle for kicking off your career. I'm all about letting things happen organically, but it is a good idea when you work for yourself to use these kinds of platforms to help build a name for yourself. When I first started and was assisting Pat, I met all the models on set who are all major models now — it's like they were all cubs and turned into big cats, which has been cool watching them all grow. For example, I'd work with Jourdan Dunn during the day doing her makeup on set and then she'd ask me to do her makeup for a night out. And then pictures would get snapped and my clients (and my Instagram page) just started to build itself. I still do Jourdan's makeup to this day!
4. It's not good enough to be good — you also have to be fast. Beyoncé told me once, "The bad thing about being good is no one is going to give you more time." And she was right. When you're speedy and good, everyone expects the makeup to be on like bippity boppity boo — *magic.* I used to practice my speed by going to clubs at the end of my regular workday and do makeup for girls there. That, plus all of that work I did on set assisting Pat or Charlotte Tilbury, is what made me quick, since all I'd have was 20 minutes to half an hour to do anyone's makeup. I used that speed to my advantage and now I'm one of the quickest guys in the business. [Editor's note: This is 100 percent true and I know this because he did a cat-eye on me in, like, three seconds. And it was flawless.]
5. Loyalty is so important. I'm only where I am because of the models I worked on when I started and still work with to this day — girls like Naomi Campbell, Karlie Kloss, Joan Smalls, Jourdan Dunn, and Liya Kebede. Naomi actually was the reason I met and worked with Pat McGrath, and now I'm at the same agency as Pat, so it's amazing to see things come full circle. And Charlotte, to this day, is still one of my biggest mentors, sources of inspiration, and has even become one of my closest friends in the business.
6. Plan out the look you want to do in advance, but always have a backup plan. When it comes to an editorial job, you often get a creative plan from the photographer and stylist in advance that doesn't really change, so it's easier to plan your looks for that. But with a celebrity, you only have a little time to discuss what they want makeup-wise. Plus, their look is so personal to them that the mood of the actress of celebrity can change at a moment's notice, which means your makeup look can change that quickly too.
7. You're going to make mistakes, so make sure you learn from them. I learned this the hard way when I was in a rush and used too much of the wrong setting powder on Naomi [Campbell]. She had the telltale white powdery sheen on her face that you could see in photos and it wasn't good. But it's never happened to me again, so I'm better for it.
8. You have to be able to switch what you're doing at a moment's notice. There are times when the talent is in your chair and she might have to take a call or look down at her computer when you're working on her eyes, causing you to have to switch up the part of her face you're working on. It's always good to be a step ahead, thinking about what you could work on next to get her ready on time.
9. You can start a new trend if you're thinking creatively. With celebrity clients, you definitely can't be doing another look that someone else has done in the past, because it will show. Plus, it's fun to create something new that everyone loves and then wears. For example, the purple lip that I created on Joan for the Met Gala. That shade wasn't really something anyone else was wearing a lot, but since then, it's become more mainstream.
10. It's not just the talent you need to please. In this business, you're never told why you're not called back. You're just all of a sudden not called back. So, you need to be in tune to the needs of everyone around you, like the publicist, the editor, the stylist, the talent, so you know you're delivering what they all want.
11. It's all about communication and chemistry. Communication is key to have with the person doing your makeup. I bring a visual and I talk to my clients about the look, so there is no room for error. For example, a smoky eye can be interpreted multiple ways, so you also have to be specific when you're talking out the look with your client to make everyone happy.
12. Your client will know her face like the back of her hand, but it's your job to know it better. No two women's faces are the same, so you have to be able to look at them and immediately know how to apply something to make him or her look even better. Like if they have an uneven brow, you have to instantly know how to lift the other side to make it even, or what feature to play up the most.
13. You'll be a lot more successful if you focus on your clients on set, not yourself. A lot of people can get caught up in just taking selfies on set or whatnot with celebs or the talent, but those people are just about the moment. But the people who are all about magnifying the celeb or the talent on set, or are making sure everyone is happy and focusing on their work, are the ones who rise the highest.
14. You need to invest in really good luggage. When you're traveling with a celebrity on tour or for a press junket, you will live out of your suitcase, so you need to have durable luggage that will carry enough clothing and protects the contents of your kit. Regular kits just don't hold up with the amount of traveling makeup artists do, so most of us turn to snowboard cases to carry our kits. They offer a lifetime warranty, they roll around the airport smoothly, they're really durable, and they fit a lot. They also split into two cases, so you can pack your clothing in one side and your kit in the other.
15. You're responsible for someone's confidence. Makeup artists are often the last people our clients see before they, for example, go to perform in front of 70,000 people. And since makeup has the ability to instantly change someone's mood, and because you'd normally touch someone up before going on stage or stepping out onto the red carpet, it's important to give them a sense of balance and make them feel good — whether it's switching up her lip color to a powerful red shade or doing a couple of jumping jacks with her to get her pumped. Your job is to raise her vibration and send her on her way with confidence.
16. "Never be jealous of your friends; be inspired by them." My good friend Jen Atkin always says this. She literally has changed the game when it comes to the atmosphere of hair and makeup artists. Rather than constantly pitting each other against one another, we now look at each other and say, "How can I learn from you or help you?"
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Carly Cardellino was the beauty director at Cosmopolitan. If you follow her Instagram, then you know she'll try just about any beauty trend or treatment once (the pics of her purple hair are on IG to prove it). But her favorite part about being in beauty is finding the most effective products, and then sharing that intel with others—because who wants to spend money on stuff that doesn't work? No one, that's who. Her most recent discovery: De La Cruz Sulfur Ointment, which will change your blemish-clearing game! Hopefully through the beauty stories she writes—and the experiences she shares—you can see exactly why she's in this business.
