Eyeliner Is (Mostly) a Confidence Game

Relinquish the fear of making a mistake and you’re at least 90 percent of the way there. While this is true of many things in life, it’s particularly important when you’re applying eyeliner—whether the look you’re going for is natural or dramatic. You can use liner in a stealth way to all but invisibly make your eyes look bigger, or use it to create the smokiest French-girl eye and the approach will be much the same. The key, experts say, is dispensing with the idea of perfection—even for something as crisp-looking as a sharp cat-eye. “It’s all in the touch-ups,” says top LA makeup artist and beauty founder Jillian Dempsey.

“Liner doesn’t have to be super precise,” agrees Chicago-based Sam Michalska, the executive director of global education at ILIA. Once you’ve zeroed in on the look you want, choose your liner and hit the mirror armed with Q-tips or cotton balls, remembering that liner is easily smudged into a sexy haze or wiped away completely. “People get stressed out about making it perfect,” says Michalska. “I get it, but all that happens if you mess up is you just grab a damp cotton bud and clean up the edges.”

“If you go too heavy or draw where you didn’t intend to, just use a cotton ball to adjust as needed,” says Dempsey.

While you might think of liquid liner as more dramatic, it’s actually brilliant for this: Because the pigment is so intense, inking just a bit of it into your upper outer lash line—think of connecting the base of one lash to the next—then wiping away any excess with a Q-tip makes your eyes stand out without reading as “makeup.” (If you find yourself applying extra coats of mascara in an attempt to make your eyes look bigger but don’t like the look of extra mascara, this is also a great tip for you.) Of course, liquid is also fantastic for bolder looks like a cat-eye, says Michalska: “Liquid delivers more precision and looks more polished.” Pencil, on the other hand, is beloved for its softer look and its ability to be smoked out and smudged. “Pencil liner gives you a more lived-in effect,” she says.

“It’s as easy as following the natural curve of your eye,” says Michalska. “Apply in short strokes or dashes versus drawing a straight line.” You can use either liquid or pencil to create a natural look. Dempsey’s technique: “Place your chin forward in the mirror and use one finger to lift your lid up to get in close. Sketch a small back-and-forth line to fill in the spaces as you draw the liner on.”

“Use a pencil with a rich, super blendable texture and intense pigment payoff. That’s how you’re going to get the most flattering effect,” says Rose-Marie Swift, the Charleston-based founder of RMS Beauty, whose pencil glides like a dream. Dempsey’s advice is to go in stages. “Don’t start with a thick line—that just makes a mess,” she says. “Gently sketch along your lash line, as close as possible to your lashes, and use your finger (or the smudge tool on the back of my pencil) to give it that worn-in vibe. It’s gorgeous on just the upper or just the lower lashes, but my favorite is applying it to both.” From there, gauge how much more you want to build up the look. “Warming up a kohl pencil with your fingers right before you use it is a brilliant tip,” Dempsey continues. “The pigment responds well to heat and the smooth glide helps you draw a beautiful shape.”

Most liner stays put pretty well, but if liner tends to travel on your eyes, here’s Dempsey’s tip: “Dust translucent powder on top to set the line.”

“Black frames the eyes best,” says Michalska. “It’s like getting a black frame for a piece of art: It makes the art—or, in this case, the eye—the focal point.” Don’t shy away from black for a more toned-down look, either, she says: “Black eyeliner absorbs light, so the colors of your eyes can stand out.”

“The more dramatic the liner, the thicker your lashes should look,” Michalska says. “When you’re amping up for nighttime, focus on building volume. For natural-looking liner or a simple cat-eye, super separated, long, long lashes look best.”

Most makeup artists smooth eye cream on their clients before starting makeup of any sort; Dempsey’s raised the bar on that step dramatically: Before you start with any makeup at all, apply one of her hydrating, firming under-eye masks, then roll over it with her vibrating gold bar—always moving upward and out to the sides—for five minutes or so. “The gold bar’s vibrations wake your skin right up, subtly lifting and toning. You can see a difference almost instantly,” she says. “And when you use it directly over the eye masks—they’re soaked in a plumping, brightening hyaluronic acid and prebiotic serum—the results are even better.” If you have time, use a little of the serum from the masks on the rest of your face and roll the bar all over for a firm, lifted look that lasts all day (or night).

“You don’t need too much if you’ve got a great eye going,” says Dempsey. “I love cream blush, tinted lip balm or light-textured lipstick, and clear brow gel for shape and definition.”