for winged liner I have to start with a fine thin edge flat eyeliner brush and use a shadow to softly put down a line to follow later.
I do this with my eyes open as I have hooded eyes and need to battle some folds to get it to look correct when eyes are open.
I only ever line the outer third of my eye and go outwards otherwise it prints onto my upper eyelid during the day.
when happy with the shape I can then go in with liquid liner or a gel liner to bolden the colour and sharpen the line.
I then set with same colour shadow or if I've used duraline I don't need to set.