Stupidity: When the Hilts discover they're 20' short of the trees, why wouldn't he "dirty up" his white/light tan pants so the tower lights wouldn't expose him so easily?
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Suggested correction: Because he would look scruffy and dirty once he got out. He was the Cooler King and knew his way around after all.
I would suggest in the reality of the escape, light colored clothing would not have been worn so as to blend in to the night and the surrounding environment better. The light slacks were strictly for artistic reasons.