The Man Repeller Learns How to Contour Like a Pro

What happens when your selfie looks better than your actual self? Web sensation Leandra Medine on makeup in the Instagram age.

I do not wear a lot of makeup. On social media, this seems to work both in my favor and against me. In response to a recent barefaced selfie taken in my bedroom on a bright Sunday morning to show off the white curly collar on my new Rodarte jacket, comments ranged from “I love that you’re so natural” to “Girl, I get that you are the Man Repeller, but would a little blush kill you?”

For years my mother has pleaded with me to get it together: “All you need is a good blush palette and mascara to elevate yourself—that’s it—so why not use them?”

Though I have always taken good care of my skin, I’ve rejected most makeup that could visibly alter (even if that means improve) my appearance. I just want to know that when people look at me, they can actually see me.

While the Internet critics tend not to offend me, I should note that on the day of the curly-collar selfie, I was filtered in Valencia—Instagram’s most efficient blemish exterminator. They thought a little blush wouldn’t kill me?

Seeing me in the flesh, where the red splotches on my cheeks and my chin were highly visible, would have, no doubt, killed them.

Don’t get me wrong—I’m not against makeup. If I could manage looking like “me” in a way that also read as tastefully, invisibly airbrushed, I’d sign up for that faster than you could choose a filter to do it for me. In this new age of round-the-clock scrutiny, who wouldn’t?

Which brings me to the garden of the Bowery Hotel, three o’clock on a Saturday during New York Fashion Week. I am waiting for Charlotte Tilbury—larger-than-life makeup artist to Kate Moss, Sienna Miller, Amal Clooney, and Cara Delevingne—who is in town from London. I am here to learn how to contour.

I’d been convinced that contouring was for reality-TV stars with on-staff makeup artists who had no qualms about having sharp, discernible, 1980s-esque slashes of blush drawn onto their faces. In fact, contouring is a sculpting and highlighting technique that, via light and dark makeup shades—not to mention an artist’s knowledge of optical illusion and forced perspective—can make you look like a perpetually filtered, better version of yourself. It can refine a jawline, whittle down a nose, and chisel cheekbones. (The ongoing debate around Kim Kardashian West’s numerous “nose jobs”? She just contours.) The former pro trick has become so popular, Sephora now holds consistently sold-out classes at their stores, and they’ve just launched an app, Pocket Contour.

Although the multishade palettes are now widely accessible—consider them the microwavable-meal equivalent of the beauty world: You can do it at home and in under a minute—the unusually dark shades and vast number of brushes are intimidating. I’d attempted to make sense of a contouring kit once before, and came out looking a little bit like a leopard.

Charlotte sweeps into the garden and immediately declares that my nose could stand to look a bit narrower, I have no cheekbones, and though I don’t need to cheat a sharp jawline (I already have one, ka-ching!), my forehead is a bit “crowded.” But the lighting back here is horrific, she says, so we go up to her suite, where from an arsenal of products from her namesake beauty line, she pulls out her Wonderglow, the facial equivalent to the body cream she calls “Gisele in a jar”—a shimmering tinted lotion that ostensibly transforms your legs into supermodels in their own right.

Tilbury lathers the Wonderglow across my face as a sheer base (“We’ve just painted your health back on”) and pulls out the Filmstar Bronze & Glow compact, “the only product you will ever need.” Generously patting her brush against the deeper Sculpt shade, she darkens my eyelids, trails slashes along my nonexistent cheekbones, and draws two lines over the bones in my nose. I leave convinced she is Hollywood’s cheapest plastic surgeon.

The whole thing actually feels a bit like psychotherapy: You can’t quite contour successfully without first figuring yourself out—taking a long, hard look in the mirror and identifying with an objective eye who you are and what needs to be fixed.

At a lesson the following Tuesday with Helen Phillips, one of Sephora’s top pros, I practice highlighting. Now acutely aware of what aspects of my face don’t work, I am ready to galvanize what does: My brows, the arches beneath said brows, my jawline, and the area above my cheekbones are begging to be lit up. “Blending is key,” says Phillips, dipping into Sephora’s Contouring 101 Palette, a round compact that looks like a game of Tetris colored in nudes and browns.

Phillips emphasizes the importance of the right brush, swapping my regular bronzer brush for a smaller one (I’d essentially been eating salad with a spoon, using that huge brush on my small face). For applying cream products like Clinique’s Chubby Stick and Tom Ford’s Shade and Illuminate (my favorites), the implement is important, too, but can I be honest? The best highlighting brush I tried is actually an appendage. Nothing has worked more effectively to bequeath to me the kind of features I’m after like my own middle finger.
The outcome was remarkable in its normalcy: I’d tinkered with the darker sculpting powders to sublimate my flaws and highlighted to celebrate my advantages, and by the end of it all, I was still just me. A “me” primed for a new and severely improved Instagram selfie, but still—just me.