The first time Chaplin donned his “Tramp” costume: Mabel’s Strange Predicament, directed by and starring Mabel Normand. From a 1933 interview, Chaplin recalls The Tramp’s inception:
“I was hurriedly told to put on a funny make-up. This time I went to the wardrobe and got a pair of baggy pants, a tight coat, a small derby hat and a large pair of shoes. I wanted the clothes to be a mass of contradictions, knowing pictorially the figure would be vividly outlined on the screen. To add a comic touch, I wore a small mustache which would not hide my expression. My appearance got an enthusiastic response from everyone, including Mr. Sennett. The clothes seemed to imbue me with the spirit of the character. He actually became a man with a soul – a point of view. I defined to Mr. Sennett the type of person he was. He wears an air of romantic hunger, forever seeking death, but his feet won’t let him.”
Note that this is not the 1st film appearance of The Tramp, based upon release date — Kid Auto Races at Venice was released 2 days earlier (on February 7th, 1914).