This thing is kind of weak; a 90 degree jack holds up much better. Check out thing: http://www.thingiverse.com/thing:882792 for a stronger version.
Create a customizable two part mold for casting a silicone sheath for a headphone jack. This can be used to create a mold for any size TRS style jack sheath.
When your favorite headdies need a new jack, tear it apart, solder on a new one and then cast your very own customizable sheath around the soldered mess.
See the instructions for customizer variables.
Print this out, plop a blob of silicone into the two halves, stick your naked jack in to the mold, and fasten it together with six M3 bolts and nuts. I've had the best luck letting it sit overnight.
I also put a little blob of hot-melt glue onto the wires to secure them before molding. This seems to give everything a bit more strength.
There is a better ASCII drawing in the SCAD file that shows what each variable controls. Daring Fireball markup HATES ASCII art.
' *[Jack Sheath Dimensions]*/ lowerDia=8.5; //Lower Diameter upperDia=5; //Upper Diameter lowerLength=15; //Lower Length upperLength=9; //Upper Length cableDia=2; //Cable Diameter jackTexture=1; //Texture depth - 0 is no texture jackDia=3.6; //Jack Diameter (add a bit to actual jack size to accommodate swelling in your print) jackLen=14; //Jack Length buttEndDia=4.5; //Diameter of butt end lengthButtEnd=1; //Thickness of butt end (stopper between the actual jack and the upper section)