It takes some practice to get this right. I suggest doing both eyes, (chances are, they'll be a little off), then choosing which one you like better. Give the angled brush a quick swipe in some eye makeup remover. Erase and correct the eye you didn't like as much to match the one you did!
Another trick to the winged eyeliner is the stamping technique. To avoid the liner pointing at 1 o'clock and 9 o'clock, try making a small mark with the angled brush and fluidline to stamp out the shape of the wing. From here, open and adjust before perfecting.
With this look, keep the skin clean and glowing by using MAC Mineralized Skinfinish Natural and MAC Strobe Liquid.
Here are two examples of winged eyeliner - disconnected and connected
