For a look that's polished and envy-worthy, wear a navy vertical striped suit and a blue dress shirt. If you wish to instantly tone down your outfit with a pair of shoes, why not introduce a pair of black leather chelsea boots to the mix? Rest assured, this getup will keep you comfortable as well as looking seriously stylish in this summer-to-fall weather. Those who wonder how to wear classic and casual dressing as you cruise through your 20s, this getup should answer your question.