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Gentlemen, when you decide that you want that rugged, 5 o'clock shadow look, there is a way to make it look good and not like you just haven't shaved for days. Most important is keeping the edges neat. If you have some hair that grows sporadically on your cheekbones, you should shave that off and leave a neater line that edges your beard. You should also shave the excess off of your neck and leave a neat edge along the top of your neck, just under your chin. Take a beard trimmer and keep the setting at 1/8-1/4" to keep it close to achieve the rugged look of the 5 o'clock shadow. You will look just dishevelled enough to look like you just woke up that way, but just neat enough to show that you care about yourself and your appearance. Trust me, gentlemen, those whom you are trying to attract really do notice that kind of thing.