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I was well into my career as a journalist in New York City before I finally realized that grown men don’t walk around town in sneakers and, when it’s a little rainy, rubber galoshes. That the first item of clothing a date looks at is your shoes. That there are a lot of subtle differences between boys and men but a well put together outfit with a sturdy pair of boots is one of the clearest signs that a guy cares how he is perceived by the world. Learn More