For a casually classic ensemble, consider wearing a black puffer jacket and black chinos — these two items work nicely together. Puzzled as to how to round off your outfit? Wear a pair of black chunky leather derby shoes to polish it off. If you feel uninspired by your transitional season fashion options, this ensemble just might be the inspo you need. Those wondering how to rock semi-casual dressing as you make your way through your 20s, this outfit should answer your question.