Consider wearing a gilet and a crew-neck sweater for a casual and cool and stylish getup. Puzzled as to how to complete this ensemble? Round off with a pair of black leather derby shoes to kick it up a notch. If it's one of those gloomy fall days, what better to brighten it up than a on-trend look like this one? Those who are curious how to pull off classic and casual style as a teenage guy, this combo should answer your question.