Photo: shvili/Mendelex_photography/elenakotphoto/iStock

Makeup shouldn't be scary (Kiss and Halloween notwithstanding), but even we have to admit some of the most intriguing trends can be intimidating. Greige lipstick? Neon eyeliner? And the one craze that (still) shows no signs of slowing down...contouring! So we called on makeup artists Molly Stern and Daniel Martin for a few pointers on how to step—or rather, tiptoe—outside your comfort zone.

Photo: PeopleImages/iStock

Super-Dark Lipstick
Not daring enough to rock greige or black lips? Neither are we. Instead, use the two shades to modify your favorite lipsticks. A layer of greige over any lipstick will turn it into a subtler shade. A coat of black creates a deeper, more dramatic hue. If you can't resist an eggplant or oxblood, keep it light and sheer. Swipe on the lipstick, then gently blot. "You'll create a wash of color, which will keep it from looking too severe," says Stern.

Top and right lipsticks: Make Up For Ever Artist Rouge ($22;
Bottom and left lipsticks: Urban Decay Vice Lipstick ($17;

Photo: Anna Galkovskaya/iStock

The key: Start small. Instead of sculpting your entire face, focus on accentuating one or two features. The easiest entry points are your cheekbones and jawline. For cheekbones, use a contour crayon or stick just one or two shades darker than your skin. Apply it in light strokes, starting right in front of the middle of your ear, moving toward your mouth, and stopping midcheek. For your jawline, start right below the front of each ear, and move along your jawline to the tip of your chin. Most important, buff the lines using a fluffy blending brush. To balance the contour shading, dab a bit of highlighter along the top of your cheekbones and just above your jawline. Again, blend well with a fluffy brush.

Clockwise from left: Nars Sculpting Multiple Duo ($39; and Maybelline New York Face Studio Master Contour V-Shape Duo Sticks ($11 each; drugstores)

Photo: elenakotphoto/iStock

Colorful Eyeliner
The trick to wearing bright and bold shades? Layering. Line your upper lashes with brown or black, then add a swipe of vivid color over the line, which will soften the effect. Choose a hue that complements your eye color: Purple is beautiful against green, emerald works best with blue, and cobalt is stunning with brown.

Shavings: Make Up For Ever Aqua XL Eye Pencil ($21;
Swipes: Elizabeth Arden Beautiful Color Bold Defining 24HR Liquid Eye Liner ($25;

Makeup photos: Devon Jarvis