Make Color Stay:

“Red lips—or bold lips of any kind—can be a bit high maintenance,” Simkins says. “To get color to stay put, try a lip primer like Urban Decay Lip Primer Potion ($20, or or a lip stain like Jane Iredale's Lip Fixation in Passion ($30,, as it fades gradually, so there’s no flaking and crumbling like most longwear lipsticks. Just make sure you apply these products to completely bare lips, as ChapStick and moisturizer can impede their staying power.”