How to Do Winged Eyeliner
To do winged eyeliner, start by applying eyeliner to your upper lash line, working from the inner corner of your eye outward. Then, draw a thin diagonal line coming off of the outer corner of your eye. The longer you make the line, the more dramatic your eyeliner wing will be. Next, draw a straight line from the tip of the wing to your upper lash line. Finally, fill in the outline with eyeliner and repeat on your other eye."
Prep your eyelid with concealer or primer. Before you apply any liner, put some eyeshadow primer or concealer under your eyes and on your lids, and blend it well. This will create a smoother, more even-looking base for your eyeliner, and will also help the liner adhere to your eyelids better. Put on some eyeshadow, if you wish. If you want to use eyeshadow, it's best to do it before you apply your eyeliner. Otherwise, your liner may get smudged and messy when you try to apply the shadow. Unless you're going for a dramatic evening look, you may wish to keep your eyeshadow subtle when you use it in combination with a winged liner. Apply pencil eyeliner to your upper lash line. Use a light pencil eyeliner to draw a thin line as close to your upper lash line as possible. The line should be as thin as possible. This acts as a base for your winged eyeliner. Start from the inner corner of your eye and work toward the outer corner. Stop at the end of your lash line. The line does not need to be especially neat at this point, even though it should be thin. You will end up going over the line again, so a little roughness will not make much difference at this point. Keep your eyelid as flat as possible while doing this. If necessary, tilt your head back and just barely keep your eye cracked open as you apply the liner. Use the pinky finger of your non-dominant hand to hold your eyelid taut while you apply the liner. Instead of trying to apply the liner in one continuous line, draw a series of dashes. It is much easier to apply this way. Measure how far out the wing should go. Hold your eyeliner pencil at the end point of your bottom lash line. Point it upward diagonally so that it looks like a continuation of your lower lash line. The line will extend diagonally up and out. If you have a hooded eyelid, you may need to angle the wing more outward than upward to avoid the hooded part of your lid. To get the right angle for your wing, visually trace a line from the outer edge of your nostril to the outer corner of your eyebrow. Draw a thin diagonal line out to act as the wing. This line should roughly match the guideline you visualized when holding the liner pencil against your eyelid. In other words, it should almost look like an extension of your upper lash line. Before you start, make sure you have a mirror around. Also make sure your elbow or arm is on a stable surface. This allows for more control over creating your wing! Begin at the very tip of the eyeliner line drawn above your upper lash line. Draw a diagonal line roughly 45 degrees out and up. The line should be heading in the general direction of the end of your eyebrow. The length of the wing is up to you. A subtler winged eyeliner look should have a short line at this point, but a more dramatic one can extend up to just below your brow bone. Never extend it all the way up to the eyebrow itself. Make a straight line from the tip to the middle of your eyelid. With your eyelid as flat and taut as possible, draw a straight diagonal line from the very tip of the wing down to the middle of your upper lash line. Keep the eye closed as you do this. Watch with the eye you are not currently working on. Put the pointer finger of your non-dominant hand on your brow bone. Pull the upper lid slightly upward to keep it taut. Draw the wing lines using your dominant hand. Fill in the outline. Use your pencil eyeliner to fill in the winged outline you just created until all the skin between the lines is covered. This does not have to be especially thorough if you plan on tracing over the pencil eyeliner with liquid liner later on. Fill in the eyeliner as close to the eyelashes as possible to avoid gaps of skin peeking through. The idea is to blend your eyelashes into the eyeliner. Thicken the line at the inner eyelid. To make it appear as though the wing is getting thinner naturally as it goes into the eye, use short strokes of your eyeliner pencil to smooth out the corner between the end of your wing and the liner on the upper lash line. The eyeliner should be its thinnest at the innermost corner, but it should appear as though it is gradually getting thinner in this direction. Place a small piece of tape at the corner of your eye. The piece of tape should extend from the corner of your eye toward the end of your eyebrow. For further guidance, the tape should line up from the nose to the outside corner of your eye, finally ending toward the tip of your brow. You should only have the tape extend from the corner of your eye to the brow, though, if possible. If you want a subtler, less angled wing, apply the tape at a slightly more outward angle instead a more upward angle. Make sure that the tape is pressed against your skin well so that no liner bleeds through as you apply it. If your skin is too sensitive to use tape on, hold a credit card or other small, straight-edged object against your skin at the same angle. Apply liner along the upper lash line. Using a light eyeliner pencil, draw a thin line above your upper lash line. This line should be as thin as possible and as close to your upper lash line as possible. Extend the line all the way to the edge of the tape. Start from the inner corner of your eye and work toward the outer corner. The line does not need to be especially neat at this point since you will go over the line again. While a little roughness will not make much difference at this point, though, you should avoid making the line too thick since doing so will make the end result look chunkier and unpleasantly thick. Keep your eyelid as flat as possible while doing this. If you have trouble doing this with your face forward, tilt your head back and just barely keep your eye cracked open as you apply the liner. Trace the edge of the tape with your liner. Starting at the end of the liner above your lash line, draw an angled line along the edge of the tape, stopping the line just below the brow bone. Do not be afraid to get a little eyeliner on the tape. If you stuck it on securely enough, the liner should not bleed through. This is especially true if you are using a light pencil liner. Carefully remove the tape when done. Go back over the line, making the outer edge thicker than the inner edge. Go back over the line of the wing and upper lash line with your eyeliner pencil. The outer edge should look thicker than the inner corner. Do not start at the top tip of the wing. For aesthetic purposes, this part should be left as a fine point. The outer part of the wing should come in at a curve. Most of the eyeliner should follow the natural shape of your eye, but the liner should be a little thicker toward the outer corner of the upper lash line and as thin as possible toward the inner corner. Step away from your reflection and judge your final look. Take a step back. Blink, walk around for a couple of minutes, and chase the look of your face from the freshest place in your mind before examining how your eyeliner looks again. Sometimes, staring at something for too long can distort our image of it. Make a judgment on your success or failure only after stepping away to give yourself a fresh perspective. Trace the pencil liner with liquid liner. Darken the winged eyeliner outline by tracing over it with liquid eyeliner. Fill in the entire outline with this liquid liner. By double-layering the eyeliner like this, you allow yourself more control over the shape. This creates a darker, more convincing wing shape. Rest the elbow of your working hand on the table or counter. Doing this will help steady your hands as you apply the liner. Make sure that you press the eyeliner wand or pen as close to the lash line as possible to prevent gaps between the eyelashes and eyeliner. Apply the liquid eyeliner in continuous, fluid strokes. Clean uneven edges or mistakes. If the pencil liner appears jagged or uneven at certain places, you can carefully clean it up by dipping an angled eyeliner or eye shadow brush into a bit of makeup remover and tracing over those edges. In a pinch, you could also use a cotton swab to erase mistakes. A pointed cotton swab can be more effective in cleaning up mistakes than a round swab. You can also use concealer to mask over any mistakes. Use your fingers, a brush, or a cotton swab and gently apply the concealer over any mistakes or unclean edges. Let dry for 10 to 15 seconds. After applying the liquid liner, let it dry briefly before you blink. If you blink immediately after applying it, the eyeliner could smear. If you do accidentally smudge a little of the liner, however, you can simply clean up the smear with a cotton swab soaked in makeup remover. Add mascara, if you want. Once your eyeliner is set, this is the time to apply mascara. Choose a color that coordinates with your eyeliner, and sweep it across the underside of your upper lashes, moving from roots to ends. 
Prep your eyelid with concealer or primer. Put on some eyeshadow, if you wish. Apply pencil eyeliner to your upper lash line. Measure how far out the wing should go. Draw a thin diagonal line out to act as the wing. Make a straight line from the tip to the middle of your eyelid. Fill in the outline. Thicken the line at the inner eyelid. Place a small piece of tape at the corner of your eye. Apply liner along the upper lash line. Trace the edge of the tape with your liner. Go back over the line, making the outer edge thicker than the inner edge. Step away from your reflection and judge your final look. Trace the pencil liner with liquid liner. Clean uneven edges or mistakes. Let dry for 10 to 15 seconds. Add mascara, if you want. 