Buddy's last three Halloween costumes have been very simple and all him.
ebay cost $14.99 (we already owned the hat). I bought it large (4T for a then 2 1/2 year old) and he still wears it, all the time. All the time. If it is clean and in his drawer, he'll chose it to wear that day. You can see from the picture it was shorts and a short-sleeved shirt. I bought what was new, cheapest and in his size on ebay. He wore sweatpants (which helped the too big of shorts stay up) and a long sleeved shirt under his costume.
In 2008 Buddy wanted to be a DHL man. I figured that costume was too hard to create (where was I going to find a half red, half yellow shirt?). Plus, UPS is just cooler. I talked him into being a mailperson and he warmed right up to the idea. His costume is a pale blue, three-buttoned, collared shirt (Old Navy) that he still wears to church some Sundays. You can't see the pants in this picture, but they are navy blue sweat pants (Old Navy) that I attached black, electrical tape to the side of to give them the dark stripe on the leg. The hat is his navy blue Red Sox hat. Then I had this black messenger bag laying around that I transformed into a mailperson bag, complete with fake mail inside. I copied the USPS symbol, reworked it to the sizes I wanted, printed them and then took them to Kinko's where I laminated them and added a clip (for the shirt badge). The other two badges are attached with safety pins.