My soft-spoken, Cat-Stevens-loving, ponytailed high school art teacher once explained the difference between the ‘realist’ and the ‘painterly’ approach to drawing a line. Realist describes itself—the line appears as it does in life, straight and true as humanly possible. The painterly line is drawn with liberty, temerity, and the confidence an artist who accepts that it’s not a strictly true-to-life line. It’s like fiction—the lie that tells the truth. The painterly line conveys movement, mood, and a sense of shifting, lived-in reality.

There are two similar approaches to applying gel eyeliner. The graphic, even-handed, realist application, and the more forgiving (but equally bold) soft, smoky, painterly approach. Luckily, a real bona fide makeup artist is here to demonstrate the techniques.

Kristin Hilton is a professional artist, and her medium just happens to be makeup (she’s worked with everyone from Dick Page to Annie Leibovitz, Glenn Close to Lucy Liu). When she talks about product, she answers only to her own artistic integrity (her favorite pick of all the liners tested was the L’Oréal). And she was glad to share her enthusiasm and deep knowledge for those of us interested (but maybe not particularly talented) in the eyeliner department.

“Gel’s great,” she says, “It’s got high wearability, and doesn’t really come off without remover.” The thing is: you have to work fast because the gel dries quickly in pretty much any formulation. The whole pot can dry out quickly itself, and oftentimes won’t be useable after three months. Hilton has a trick for a desperate hour, though: “Even when the pot seems dried out, you can still reactivate the product by warming it up on your hand.”

So how do you get it to stick? You’ve got to make sure your skin is super-clean. Eye cream or oils (even from an oil-based makeup remover) can stay around, even overnight, and make your eyelid-canvas too oily to hold a straight line. But don’t toss out those oils altogether—Hilton (like the rest of the breathing population) loves coconut oil. “It’s great for removing heavy makeup, especially heavy color, and color with reds or violets.” If you’re coming off a Broadway stage or a parade float, Hilton recommends dissolving and wiping away all that makeup with coconut oil and then using a little makeup remover afterwards on your lids. Hilton’s favorite removers are Bioderma and Koh Gen Do’s Spa Cleansing Water—dab a little over you lids in the morning before applying liner to make sure there’s nothing there but gel and skin.

The painting process can sometimes seem daunting—lids used to take Hilton a half an hour at least—but the freedom, coupled with a tiny paintbrush should feel liberating. You could do just about anything. “I promise, you will get better,” Hilton assured wary-eyed onlookers. Now take a deep breath and steady those hands.

If you end up with an imperfect line, or if you come out looking a little sad and jagged, you can always take a small eyeshadow brush and blend a little soft bronzy shadow on the lid and line after the gel sets a little. It’s a softer effect altogether, a painterly rather than a graphic line. Either approach is beautiful, strong, and a fine use of the medium. So paint away—any way you like.

Liners in order of appearance: Napoleon Perdis China Doll Gel Eyeliner in Yang , Laura Mercier Crème Eye Liner in Canard , Jane Iredale Jelly Jar Gel Eyeliner in Purple , Nars Eye Paint in Baalbek , Maybelline Lasting Drama Eyestudio Gel Eyeliner in Eggplant , Revlon Colorstay Creme Gel Eyeliner in 0 07 Rio Blue , NYX Gel Liner and Smudger in Brown , Bobbi Brown Long-Wear Gel Sparkle in Thunderstorm , L'Oréal Infallible 24HR Laquer Liner in Blackest Black , and MAC Fluidline in Blacktrack .

June Downs (New York Model Management) photographed by Tom Newton. Makeup by Kristin Hilton (The Wall Group).