Abstract: A new and improved clothing anchor apparatus, especially useful for anchoring the front and back tails of shirts, includes a first clothing connector, a second clothing connector, and an elastic strap connected therebetween. The elastic strap has a first end, an interior portion, and a second end. A strap length adjuster is located on the interior portion of the strap for adjusting the effective length of the strap. The effective length of the strap is adjusted by adjustingly doubling a portion of the strap. A soft, flexible jacket encompasses a portion of the elastic strap and the strap length adjuster. The jacket may also include a pocket for receiving and secretly storing soft, flexible items such as paper money. In use, preferably, two clothing anchor apparatuses of the invention are used. One clothing connector of each apparatus is attached to the front shirt tail, and the other clothing connector of each apparatus is attached to the back shirt tail by first passing under the crotch area.