If you want to look "Rough" keep the hairs on your chin and under your bottom lip shorter and stubbly. Also, if you can, try and keep a 5 o'clock shadow type of deal.
This may sound weird, but I've always used a hair clippers to maintain my chinstrap. I put it on the 2nd setting with the bare blade and go over my hair about once a week. It leaves about 2-3mm of hair, which is perfect for that "rugged" look. It also takes all of 10 seconds.
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