I'm looking for tips, articles, links, sample shots, etc. for styling my 2 year old DS for headshots. I'm so tired of polos and keep getting drawn to plaids...

Check out: http://liltoesphotography.com/

I did newspaper caps, skinny jeans, vest, etc.

We were told to stay away from white shirts (unless DS has dark skin) and black (too dour). Also, plaids are fine if they are small and subtle. Avoid big plaids and bold stripes unless you have something solid over them -- vests or jean jackets are great. A hat is fine but only as an extra photo -- CDs will want to see your son's hair.
Go on IMDB and look up some child actors and see their headshots. Or google some good child photographers and scroll through their photo galleries.
Good luck!

You don't need headshots for a 2 yo. Best to do snapshots because they change rapidly at this age. I wouldn't do HS until at least 4. Did you manager or agent tell you to get them - if they did then they should tell you how to dress.

I know we don't need headshots - and our agent didn't tell us to get them. Just decided to take our photos we take each year to commemorate the birthday with a headshot photographer so we can use them for both work and family. Thanks to those who have provided wardrobe advice. I'm going to have to find one of those newspaper caps for one of the final shots after we get some good ones with hair showring.