A footwear upper having a collar assembly that is joined at its forward edge to the lower portion of the upper by a flexible region of material so that the collar may flex forward and rearward in relation to the lower portion of the upper. In one aspect of the invention, the upper includes a neck portion that is telescopically overlapped by the collar. In another aspect, the upper includes a gusset that extends between the lower portion and the collar, with at least a portion of the gusset being substantially hidden from view.