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For a special night out, do something out of the ordinary with your makeup. Practice first so you don't end up looking like a beauty “don't”.
If you tend to go light on the eyeliner during the day, you might want to try a simple smoky eye with killer shimmery grey eyeliner. Try one that is soft and easier to apply so that you can layer it on and smudge it for a smoky effect. For the first layer of liner, get the color as close to the lash line as possible. Then you can build wider and thicker lines on top of the first one.
The smoky eye look is great because it doesn't have to be perfect. Make sure to wear a neutral colored lip gloss or lipstick, since your eyes will be the focus. If you are really in the mood to be daring, add a couple of individual false lashes to the outer corners of your upper lash line. Your eyes will be fab, and BAM! You are ready for a night on the town.