Follow these tips and it should make this milestone go more smoothly. There are several ways in which you can successfully prepare your child for a visit to the hairdresser. It probably sounds a bit silly  to role play, but experience has shown that for many children a hair cut can be a bit scary. It's a situation that is unfamiliar and also involves strangers getting quite close to them.

Gather together some play "hairdressing" equipment. All you really need is a pair of play scissors such as the ones included in many children's doctor kits, some combs, some brushes, a squirt bottle with a little water, and lastly a small sheet (crib sheets work well). Also find a little chair for them to sit on. If you have a mirror, it  would be great  to use it too. The point is to make the role play as similar to the real experience as possible.

Now the fun starts. Explain to your child that you're going to pretend to play hairdressers. Model all the things that will happen during his visit. For example, greet him; sit him down in the special chair; and ask him what he would like to have done. Be silly and have fun with it. Put on the "cape" and brush his hair and dampen it a little with the squirt bottle of water. Now for the tricky part, pick up the pretend scissors (you don't even really need to use any scissors--you can just pretend) and role play the whole experience ending with paying for the haircut. Children just LOVE to do this. Now it's time to reverse the roles and allow your child to be the hairdresser. This is quite important because it allows the child to gain a sense of mastery over the whole experience; and, therefore, develops his confidence. 
To avoid the inevitable cutting of "real" hair explain that this is something only hairdressers do. Then make sure ALL your scissors are safely put away! Curious hands can get really creative with cutting hair. Don't we all have memories of doing this ourselves?

When you arrive at the hairdresser,  just remind him of all the things that will happen: sit down in a chair, put on a cape, get your hair brushed and wet a little, and then the scissors come out to cut the hair. Some children think that they are actually going to get cut! So gently remind them that it's only their hair that is getting cut, not their skin. Talk to them the whole time about what the hairdresser will be doing. 

You could even bring a familiar book from home and read it to them as they are getting their hair cut. I have done this on several occasions and it has worked really well. Especially if you let your child choose the book to bring along.

Source:www.sixtysecondparent.com