Wet your toothbrush with cool water and dip the bristles in a shallow bowl of sugar. Gently brush your lips with the brush, adding more sugar if necessary. The sugar acts like a mild exfoliant to brush away dry, dead skin that leads to caked lipstick. Rinse your mouth with water and dab dry on a towel.
Apply a thin layer of lip balm to your upper and lower lip approximately 10 minutes before applying lipstick. Lip balms, especially those made with beeswax, plump up and soften lips for smooth lipstick application.
Add two small drops of lipstick primer to a clean lipstick brush, and sweep over your lips. Extend the primer just beyond the edge of the lip to prevent feathering. Press your lips together gently for even primer distribution.
Line your lips with nude lipstick liner. Liner holds lipstick on your lips and keeps it from bleeding outside your natural lip line. Pick a color that matches your skin tone for a seamless blending between lips and skin.
Sweep your lipstick brush back and forth over the lipstick and brush it on your lips. Work from the center of the lips outward, working in short strokes. Applying lipstick with a brush reduces the chance of putting on too much lipstick that will cake up throughout the day.
Splurge a bit when picking out new lipstick. Cheap lip color is made with lots of wax and other fillers that cake up rather than evenly coat your lips. Shelling out $20 or $30 for a tiny tube may hurt your wallet, but your lips will thank you.