Yes, visit a barber.
Barbers are like hairdressers, but for gentlemen. It's almost like a time-warp to the fifties. Instead of getting your haircut by a fifteen year old first year apprentice who dropped out of school, you'll be getting your hair cut by someone with experience. Similar to a man's shoes, his haircut says just as much about him.
For example, if you have hair as long as a Swedish death metal guitarist, it probably means you're lazy and don't care about your appearance. If you have green/purple/blue hair it probably means you think you're ugly and having a stupid colour in your hair will draw attention from that. If you have a faux-hawk*, you're a douchebag. Observe:
Douchey douche douche McDouche.
Going to a barber is an experience. They will ask how you want your hair cut. They won't assume anything, and they will ask questions. Every hair above your neck will be accounted for. Eyebrows can be trimmed, beards can be shaved and so on. If you're not sure what you're after, you can ask for their recommendation. Whatever you do, don't get a haircut where you'll look back in ten years and ask yourself what you were thinking.
They won't judge you, as it's their job to cater to your needs. It doesn't matter if it takes longer or if it's difficult. It's their job to do so. Different people come in and ask for different things. Don't be afraid to do the same.
If you know me, you'll know that I love a good haircut. I have two basic requests when getting spruced up with my number three all over:
1) Scissor over comb: Classic haircutting method. If your hairdresser/barber doesn't know or want to do this for you, leave immediately. It certainly takes a lot longer than clippers, but it's worth it. It won't be perfect and uniform, but that's the point. There'll be a few missed hairs here and there - but it prevents the awful 'just got my hair cut' look. It looks natural. Clippers are now your enemy.
2) Straight razor on the neck : Instead of getting a little clipper (which tickles incessantly) to clean the back of your neck - get it lathered and shaved. You can get your neck line faded or squared off. I personally prefer squared off as it's neater.
Forego shaving for a week or two, let them take care of it and get pampered like a man. Especially in this month of Movember what better way to clean up the mess on your upper lip, than a trip to the humble barber?
-Loic
*Since faux-hawks are unforgivable, I decided to get a real one for Tough Mudder earlier this year. Went to the barber's the next day:
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