What you'd expect: Dark Crimson
A blue-toned red lipstick can feel formal, but orange-reds—even deeply pigmented ones—have a more playful vibe. Keep the rest of your face almost bare (our model is wearing only mascara, concealer, and a brow pencil), leave your hair loose, and rely on eye-catching lipstick (here, Black Up Lipstick in 18) for a casual look that's also terrifically polished.
Pull It Off Like a Pro
Find your formula. If you have warm, golden, or olive skin, any orange-red will look gorgeous—even the most saturated, matte version. On a pale, cool complexion, an orange-red gloss or sheer stain is more flattering.
Do border patrol. To prevent a bright lipcolor from bleeding, trace a pencil concealer (like Urban Decay 24/7 Concealer Pencil, $18; Sephora.com) around your lips. Buff it with your finger, then apply color.
Start in the middle. Your lips look fuller when you dab lipstick in the center of your mouth and blend it out with your finger. Blot gently with a tissue to remove excess color.
Don't rush blush. Apply lipcolor first, then assess how much blush you need. A vibrant lipstick often brings out the natural rosiness in your cheeks. Avoid bronzer altogether—it can look muddy against a rich lipcolor.