To put together a casual ensemble with a modern twist, you can opt for a charcoal hoodie and brown chinos. On the shoe front, go for something on the classier end of the spectrum by rocking casual boots. There's no nicer way to cheer up a gloomy fall afternoon than a cool getup like this one. Those wondering how to pull off classic and casual dressing as you go through your adolescence, this combination should answer your question.