When I was 14, I had Margot Tenenbaum-esque black-rimmed eyes and a terrible crush on a violinist in the Omaha Area Youth Orchestra. He was incredibly talented, and with his torn jeans, over-sized flannel shirts, and disaffected attitude, he was youth philharmonic's answer to Jordan Catalano. He sat at the other end of the orchestra (I played the french horn), and we didn't really have any of the same friends (he mainly hung out with strings). It was a pretty distant pining, until one day during a rehearsal break. I was reading in the hallway, trying desperately to look bored and Angela Chase-esque, when he walked by and called me his "sad tomato." I was completely confused. He called me this curious name several more times throughout the year, but I was always too nervous to engage in actual conversation. Finally, I mustered up the courage to respond, "So, are you going to, like, clarify any one of these days, or what?" Aw, to be young and articulate. He explained that it was from an R.E.M song, and that I was his "Crush With Eyeliner."
Sadly, our romance was short-lived. At the time, I thought R.E.M. was pretty wussy (still kind of do), and, fickle kids that we were, he developed a crush on another violinist, while I developed a crush on a percussionist. What did last was my obsession with kohl-rimmed eyes. Well, and attempting to look bored and Angela Chase-esque. The key for creating a dark, messy eye is to let go of your usual precision. This is not a cat eye. It is not liquid liner and it is not meant to look perfect. This can be surprisingly difficult for beauty perfectionists to achieve. This isn't the time to worry about long-lasting, non-smudge formulas. You need an eyeliner that soft, dark and blendable.
A great option is Benefit's BADgal eye pencil. With its soft, powdery consistency, blending this eyeliner with a smudger is almost like working with eyeshadow. If you're going for serious blackout, double-team BADgal with a long-lasting liner on the waterlines of your eyes. Try applying Maybelline Unstoppable Eye Liner in black to the inner rims of the upper and lower lids. The upper lid can be tricky at first, but once you get the hang of it, you'll be amazed at how much thicker it makes your lashes look. Then pile on the layers of mascara. And don't worry about clumps, they just show that you, like, totally don't care.