I know this isn’t really the time of year for this, but I have bought Halloween costumes (the non-scary and gross kind) the day after Halloween for cheap. We have a dr. outfit, police outfit, and a cowboy from that. We have also gotten inexpensive cowboy hats at Wal-Mart/Bass Pro that my 3 boys love to wear. We also have reindeer antlers from the $1 isle at Christmas that they pretend to be deer with. They too are fans of the firefighter – I don’t know if you have a Firehouse subs nearby but they give away free hats – we have lots. We have a knight set that was a bday present from Target for around $20 I think. And we have the Davy Crockett hats (which my two year olds are afraid of). They also like to put on their orange toboggans and a camo shirt and pretend to hunt like Daddy. The little two like to just wear their older brother’s clothes and pretend to be him! 🙂 There is always the paper sack vest that can be decorated any way you need it to be. Overalls and a tool belt and they are construction workers. We also have small aprons and chef hats (I got the hats at a kitchen store for cheap, the aprons are give-aways, but can easily be made) and they like to cook. That’s all I can think of right now that is in the dressup box. As for my boys, they are usually content with a hat or one piece of an outfit and they are instantly someone else!