Teri Tobias in O magazine

Teri Tobias has a purseful of pale, sheer lip glosses with names like Petal and Blossom. "I'm completely comfortable wearing a vibrant scarf or sweater—but bright lipcolors intimidate me," says the 36-year-old New York City literary agent. "Though they look gorgeous in the tube, they're a completely different color on my lips. I need help figuring out which shade to choose and how to wear it." We asked makeup artist Rebecca Restrepo to ease Teri out of her lipcolor comfort zone…and into a rich, thrilling red.

Learn the expert technique for wearing red lipstick
Finding the right shade of red lipstick

The color of the pads of your fingers is similar to that of your lips, so they give you an accurate picture of how a shade will look on your mouth (and you won't risk ingesting nasty microbes at the department store counter). Swipe a range of colors on your fingertips and see which ones look best. Then hold your favorites close to your mouth to decide which one is most flattering; the right bright shade will make your eyes sparkle and won't bring out redness in your cheeks. For Teri, Laura Mercier Lip Stain in Mulberry ($20; Sephora.com ) was a perfect fit.
Putting on lip balm

Without this prep, a bold lipcolor will draw attention to any cracks or flakes. Just a dab will do (too much and your lipstick won't adhere).
Applying red lipstick

Whether your lipstick comes in a tube or pot, using a brush to apply it gives precise edges. Start in the middle of your mouth and move out to the corners.
Bold lipstick

With bold lips, the rest of your face should stay subdued: Use a pencil to define your brows, apply a couple of coats of mascara, and you're done.

More Step-by-Step Makeup Guides