Talk to your barber/hair stylist. That person knows your head inside and out and can advise you on the best style.

Also take his/her styling to heart. I don't really like the hairstyle he gives me when I'm done with the haircut, but for some reason it is very similar to my 'just woke up 5 minutes before the train gets here' hairstyle (which is basically bedhead) - people love it when I have that hairstyle, for some reason.

My hairstyle takes about 2-4 minutes to do.