Why They Say Paint the Town Red Or Put On Your Thinking Cap

PUT ON YOUR THINKING CAP

Meaning: Carefully and thoughtfully consider something
Origin: In previous centuries, it was customary for judges to put a cap on before sentencing criminals. Because judges were respected thinkers, it was referred to as a “thinking cap”

PAINT THE TOWN RED

Meaning: Spend a wild night out, usually involving drinking
Origin: “This colorful term … probably originated on the frontier. In the nineteenth century the section of town where brothels and saloons were located was known as the ‘red light district.’ So a group of lusty cowhands out for a night on the town might very well take it into their heads to make the whole town red.” [via]