In regards to McClellan's hat, that is his military issue 1840s style M1839 forage cap or sometimes called a "wheel hat".
http://www.dirtybillyshats.com/US2.htm.html
http://www.history.army.mil/images/artphoto/pripos/amsoldier/1/1847.jpg
http://www.dirtybillyshats.com/US2.htm.html
http://www.history.army.mil/images/artphoto/pripos/amsoldier/1/1847.jpg
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