I used to always carry my eyeliner around in my bag because it would wear out through out the day. So over the years I have realized this to be the best eyeliner combination/application for long lasting eyeliner.
Step 1: Cream Liner
I discovered cream liner from one of my friends. I had only ever heard of regular eyeliner pencils and liquid eyeliner before this. Cream liner comes in a little bottle like this and is applied with a brush. It is waterproof and last the whole day. I like to put this on first before my eyeliner pencil. Just applying a little as the base to my eyeliner regiment tends to make the eyeliner pencil last longer, smudge less, and look awesome!
It is hard to find cream liner in a regular drug store. I bought mine from Clinique, but most high end makeup brands carry their own version.
Use a eyeliner brush to apply the cream eyeliner. The eyeliner can be pretty heavy if you just put the brush right into the cream liner and then apply it to your eyes.
First I dip it in the cream liner (just get a little on the tip of the brush). Then I spread it out on the inside of the lid of the cream liner with the brush so there is just a little on the brush. While I am applying it to my eyes, if I need more eyeliner I just take some from the inside of the lid.
When applying start from the inside corner of your upper lid and brush out towards the outer lid. If you mess up I usually just take the other end of the brush and smudge it so it looks like I did it on purpose.
Step 2: Eyeliner Pencil
Just apply the second coat of eyeliner with your eyeliner pencil the way you normally would and you're good to go!!