Date determins if this is a Jefferson Bootie or a Brogan.  Prior to the invention of the sewing machine, all construction was done by hand. So, from about 1800 to about 1840, Jefferson Booties were sewn by hand. From 1840 to 1900, Brogans were a popular type of footwear.  After WW1, the same shoe was called a Chukka. This is still a very popular style of footwear.