[Charlie Chaplin as The Tramp — One’s fashion should exist in the context of one’s personality. This is why you can wear an incredibly well-tailored suit, but if it’s not a reflection of who you are and not useful to what you do in it, then you’re not well-dressed.
Charlie Chaplin’s tramp outfit is a beautiful example of this, especially in the context that the tramp is both a compassionate and a comical character. His shoes are way too big, his pants are huge and baggy. His coat is too small, making it extremely tight. Along with it he always has a bowler hat and a cane. The big shoes and baggy pants add a hint of clown-like clumsiness to the character, as well as allow the actor to wear protective clothing underneath for all the prat falls. The too-small coat allows for his posture and shape to be seen, as well as his arm gestures, all of which are very important for a silent-era movie star trying to convey emotion. The tight coat also creates a balance for the bagginess of the pants. The hat and cane not only add a more specific detail to the character, they are both incredibly useful for doing things with. One of the two is involved in more than half of the jokes Chaplin did, and I would argue both are a vital part to everything the tramp is. The outfit works with the personality of the Tramp because it’s all a basic man’s outfit of the period slightly stretched out of proportion, but still in the realm of realism — He still looks like a believable person, which is how the character can be both comical and compassionate. And as a practical outfit, it allows the actor himself to do endless pratfalls, to convey emotion, and to tell thousands of jokes. It’s understandable The Tramp hardly ever wore anything else.]