1. When I am doing my eyeliner at home, I sometimes like to use black eye shadow and sketch an outline to start. You can also 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.
Make sure to start from the inner corner of your eye and work toward the outer corner. Don’t worry about it being neat at this point, even though it should be thin. You will end up going over the line later. Keep your eyelid as flat as possible without pulling your eyes.
2. Measure how far out the wing should go. You can hold a spoon or your eyeliner pencil at the end point of your bottom lash line and point it upward diagonally so that it looks like a continuation of your lower lash line. Again I personally like to do a sketch with black eye shadow before running over it with black eyeliner. When you start to draw the line it should extend diagonally up and out.
3. Draw a thin diagonal line out to act as a wing. This line should match the guideline you visualized when holding the liner pencil or should match the black eye shadow you placed as a sketch. Make sure you are doing this in front of a mirror and you have a stable arm that allows more control. Start at the very tip of the eyeliner line you already drew on your upper lash line and draw a diagonal line roughly 45 degrees out and up. The length of the wing is up to you. Never extend it all the way up to the eyebrow itself.
4. Make a straight line from the tip to the middle of your eyelid. With your eyelid as flat 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 and watch with the eye you are not currently working on.
5. Fill in the outline. Use your pencil eyeliner to fill in the winged outline you just created. Try to 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. The eyeliner should be its thinnest at the innermost corner, but it should appear as though it is gradually getting thinner in this direction.
Now Voilà! You are done!