Do I need a haircut? Watch
Obviously if the guy is going for a longer hairstyle it will be longer, but the needs to be kept trim to that length once achieved to look good.
I would guess you are around the two month mark so yes about now is probably good as otherwise it could get very overgrown and messy looking. I think once a good bit of turf is growing at the front sides of the ear then it's about time to go in my opinion.