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Applying eyeliner the right way takes a little practice. First, make sure you have a liner that isn't dried out so that it goes on as smoothly as possible. You don't want to pull or tug on your delicate eyelid skin. My favorite eyeliners are the gel-based ones that twist up so you don't have to sharpen them. It saves time because you don't have to dig around for a sharpener, plus they go on smoother than the regular wooden pencil-type eyeliners.
Remember: it's not necessary to draw a continuous line across your lid. Position the pencil as close to the lash line as possible and wiggle it back and forth, drawing little dots directly into your lashes. Then, connect the dots, or smudge it all together, with a sponge tip or Q-tip. Most twist-up liners have a sponge tip made especially for smudging on the other end of the product.
Don't make the line too bold and exact, especially for day wear. Eyeliner should define the eye and not look too obvious. If you are after a more natural look, you should stay away from using black. A soft plum, khaki, or brown is perfect, and looks like you aren't trying too hard.