When you want your face to look dressed-up but not made-up, color your lips a rich shade of plum; it's bold but has a cool elegance you won't get from a candy-apple red (and still works beautifully with vibrant shades like the orange our model is wearing at left).
A matte finish is more glamorous than high shine; Pati recommends simply tapping a creamy lipstick over bare lips with your finger. Then tidy up the outer edges—and create a barrier against bleeding—with a pencil (for the most natural-looking line, use the side, not the point, to draw short strokes); the pencil shade should be as close as possible to the lipstick without going darker (Benefit Silk Lip Pencil in Sangria, $18, is a good match for many iterations of plum).
A strong mouth brings out the flush in your cheeks, so go light on blush, but do take a couple of minutes to define your eyes. Run a rich brown liner pencil (like MAC Eye Kohl in Teddy, $14.50, which has a touch of iridescence) as close as possible to your upper and lower lashlines, then finish with two coats of black mascara.
3 Pairings for 3 Skin Tones
A perfect match between your lips and nails can be a little much. But two pretty variations on the same shade create a sophisticated symmetry.
If you have fair skin, try blue-based berry colors with a bit of translucence.
Prescriptives LipShine in Black Cherry, $17.50; SpaRitual Nail Lacquer in Impression, $9
If you have olive/medium skin, try creamy, succulent, red-tinged plums.
Clarins Joli Rouge in Plum, $23; OPI Nail Lacquer in Bastille My Heart, $8.50
If you have dark skin try deep, saturated raisin hues.
MAC Cremesheen in Hang-Up, $14; Essie Nail Color in Wicked, $8