I don't know if it's just me, but recently lipstick and I have not gotten along. My lips will be feeling good all day long and then the minute I decide to add a splash of color it all goes south. Chalk it up to changing seasons and dry skin? Maybe. Whatever the reason, I use two products to combat this issue:
Lip Scrub: There are so many varieties out there of lip scrub it's hard to mention just one. They range in price greatly, but they have one purpose: exfoliate all the crap off your lips. All the dead skin, peeling parts, and general seasonal dysfunction on your lips will be scrubbed away. Take a little tiny bit (think pinky fingernail) and scrub in circular motions. Current favorite? Sweet Lips by Lush. If you are feeling especially broke here is a recipe to make your own.
Aquaphor: If you are reading this and you don't own Aquaphor you need to shut down your computer and get to the drugstore. This petrolatum (read: vaseline) based ointment is meant for burns, scrapes, and other minor abrasions to your skin, but it absolutely takes the cake in lip care. It's the best lip balm $4 can buy and will soothe all the cracks that tend to shine thru this time of year. I put it on before lipstick for a smooth base and I lather it on before bed so I wake up with baby smooth lips.