A shirt retaining assembly including a chain assembly, a shirt button connector assembly and a buttonhole connector assembly. Chain assembly includes a chain, wherein the chain is a jewelry chain with an S-shape connector attached in and edge thereof. Shirt button connector assembly includes a round member attached to the S connector, wherein the round member has a circular shape that can be placed underneath a shirt button. Buttonhole connector assembly includes a post attached to the opposite side of the chain, wherein the toggle is attached vertically aligned the post by means of a free end. The toggle can be introduced in a buttonhole allowing the shirt to keep stable while unbuttoned.