The history of wingtips is tied up in that of the brogue.
Brogues are a 16th-to-17th century Scottish/Irish invention. They were shoes made for wading in water; the perforations were functional and served to let the shoes drain. Nowadays, the perforations are purely decorative. For a long time, brogues were strictly country shoes, but the blurring of the lines between country and city wear has made them more acceptable for town.