Applying Lipstick That Sticks
Apply concealer or powder. A coat of your concealer will help to secure your lipstick and make its colors more vivid. Try liquid concealer under glossy lipsticks, and powder under matte lipsticks.
Apply lip liner. A thorough coat of lip liner will help your lipstick cling in place. Use a nude shade of lip liner if you'll be applying sheer or neutral lipstick, or try to match the liner to the color lipstick you'll be wearing. Coat your whole pout with lip liner, but avoid filling in your "inner lips" where the teeth naturally hits the lip.
Apply your lipstick within the lines using a lip brush. Apply your lipstick evenly and within the lip lines. Blot your lips with a tissue to remove excess oils from your first coat, and add a second coat of lipstick to the outer two-thirds of your lips. In addition to providing more vivid colors, a second coat will provide longer-lasting coverage. Using a brush will make it easier to get a precise application, and you'll be less likely to apply too much in any one spot.
Put your finger in your mouth. Form an O with your mouth around your finger, and gently slide your finger straight out of your mouth. This step will remove any lip color remaining on your inner lips, keeping your teeth pearly white. You can also remove any excess lipstick by blotting your lips several times with a tissue.
Check your smile. Smile in the mirror and check your teeth for any lingering color. If you see any lipstick, gently rub it away with your pinky finger.
Maintaining Your Lipstick On-The-Go
Eat with care. Try to eat small, bite-sized pieces of food that require minimal contact with your lips. If you anticipate needing to snack, try to bring something small--like nuts or crackers--which will be easy to eat with little lip-contact. If eating something large and unwieldy (like a burger) is unavoidable, you may be better off blotting away your lipstick before digging in; it will likely be removed anyway.
Drink with a straw. Minimizing lip-to-glass contact will keep your lipstick from smudging. If you must drink straight from a glass, try licking the edge you’ll be drinking from, and only take sips from that spot.
Don't bite your lips. Be careful not to subconsciously chomp down on your pout; doing so is sure to smudge and mangle your lipstick.
Keep some extra lipstick and concealer handy. If your lipstick does end up smudging while you’re out, you can easily touch up your coat or cover over smudged edges.
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