My 7 month old boy is my secret weapon in this department.
Holding him and saying things like "look at the pretty wall, isn't it a nice wall? Do you want to touch the wall? Oh, you want to see the hole in the wall?" Perfect cover!
There is a cache on a pedestrian crossing in the center of my town I'm going to look at tomorrow. He'll certainly be coming with me!!
The clipboard/hat/vest thing sounds wonderful. I work for a company that cooks/cleans/maintains/secures so my uniform will be the perfect disguise!