“Going where the weather suits my clothes” is an old hobo saying from the early 1900s. Fred Neil, a singer songwriter, used the phrase in 1966 when he wrote Everybody’s Talkin’. The Harry Nilsson version of Everybody’s Talkin’ was a hit in 1969. It was an even bigger hit after it was featured in Midnight Cowboy.
The song is about not being able to connect with the busy bustling world and wanting to go back home to a simpler time. The cool thing is, the guy who wrote this song, Fred Neil, he made enough in royalties to do what he wrote about. He moved back home to Florida and retired into obscurity.