I think it will take a bit of practice to apply eyeliner. You also have to find the right thickness for your eye. To start off, I suggest using a pencil. Clinique makes a great retractable one that is super soft and really easy to apply. It might take a few tries to find out what works best for you! I suggest the color New Black which is a grayish black.
When I first started I used Rimmel liquid and pencil. However, you might want to use the pencil first to get the hang of it. I got the liquid in my eyes and it burned so bad. But the pencil goes on easy, doesnt run (for me anyway) and is affordable!! I promise the pencil does not hurt, if that is a concern! Good Luck! Hope I helped!
Answered[ Edited ]
I agree with Melissa; liquid liner can be really difficult if you're just starting out, so I would actually start with a pencil. Pencils -- preferably ones that sharpen -- are much more user-friendly!
If you prefer liquid, a good compromise is the new Too Faced 3-Way Lash Lining Tool. This thing was a dream for me -- the tip is three *very tiny* flat points, which makes it so easy to dot along the lashline, both for lining and tightlining -- the line ends up being really precise. It's liquid, but the applicator is nearly foolproof...I really like it and find it easy to use (and I'm not particularly skilled when it comes to liquid liner...I always wind up looking like the Evil Queen).
If you're a beginner and just want to play around and experiment I recommend buying a drug store brand, they are cheaper and it's no big deal if you need to replace it.
I recommend CoverGirl or Maybelliene, I always had luck with them when I was starting out.
I would also stay away from liquid until you get the hang of using a pencil. I recommend a self sharping eyeliner, it is less hassle and less of a mess.
If however, you want to go with a higher end eyeliner I recommend Urban Decay's 24/7 in Perversion (super black!) or a Make Up For Ever Aqua Eyes eyeliner. They are super creamy and can come in a variety of colours if you're up for it.