The present invention entails a handkerchief holding system for efficiently positioning and retaining a handkerchief within a structure. The handkerchief holding system includes a housing having at least one wall and an opening exposing an interior cavity, a spring extending about a portion of the perimeter of the housing, and a clamping apparatus extending about the opening of the housing. The housing is positionable within a shirt breast pocket for conveniently retaining a handkerchief within the breast pocket of a shirt. The clamping apparatus is capable of retaining and supporting the handkerchief in a desired partially exposed position within the pocket.