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Look for things that say Safe for contact wearers or hypoallergenic on the back of the package before you purchase the eyeliner. These usually go on more easily than regular liner and they won't irritate your eyes as much when it is on. Also look for an eye-liner that says it will not tug on the skin, as this is usually the main problem as the eye area is so delicate. Test eye-liners on your hand before buying to see if they draw smoothly, you don't want to have to press a lot to get out colour.
Liquid eyeliner also proved to be very difficult, especially while trying to apply it while your eyes are tearing up. Waterproof only means waterproof once the liner dries, if your eyes are tearing up while applying it, the liner simply slides off of the eyelids.
If your skin or eyes are really sensitive, cleaning off the outer layer of your pencil before you line your eyes removes bacteria and other irritants that might have settled on the pencil. Having a sharp tip also means that you'll use less liner because you'll be able to get a clean sharp line on the first try, which lowers the chance of smudging.
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