Teri Tobias in O magazine

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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