Pick the smallest wire that carries your current without overheating and without dropping too much voltage, using the derating method of MIL-W-5088L: free-air rating (figure 3), bundle derating (figure 4) and altitude derating (figure 5). Every step is shown, with a link to the place in the specification it comes from.
A design aid, not an approval. MIL-W-5088L is inactive for new design and has been replaced by SAE AS50881, which is copyrighted and not reproduced here. Verify every result against the specification and wiring standard that governs your program, and against the ratings of your connectors, contacts and circuit protection (3.8.8.1.2).