this is from the '95 FSM wiring diagrams page 114 (8w-51-4 in 95yj_8w.pdf file), i can't remember what year of vehicle you have so the colors could be different: on your stock tail-lights the vehicle should have 4 wires
ground - black
tail light - black with yellow stripe
brake/signal - dark green with red stripe for left side, brown with red stripe for right side
back-up light - violet with a black stripe
you should connect the tag light to the tail light wire which is the one that is hot when you turn your lights on - black with yellow stripe in this case
the other wire should be connected to ground - look if the tag lights have a ground wire connected there so make sure you don't connect them backwards as it could give ground thru the mounting screws as well and you could blow a fuse
i would use a weatherpack or metripack 1 pin or 2 pin connector depending how many wires you have on your tag light to hook into the harness, that way you can disconnect the tag light and remove it no problem - NAPA or such store should have those. If your grommet is small i would consider using 2 singles (2 x 1 pin connectors) to make sure it can pass thru the grommet.
Best is like you said to solder and use shrink tubing, but i would suggest using a bit of RTV on the wires and soldering before sliding over the tube and heating it to shrink, since you would have 2 wires side by side one could pull the tube apart and let water and dirt in there.
hope this heps
EDIT: 1995YJ beat me to it but he's got different colors so see which one matches, i didn't check on the vehicle and my info was from the FSM