For a casually dapper ensemble, try pairing a yellow raincoat with a black and white print hoodie — these pieces work well together. Black suede low top sneakers will pull your whole look together. As you can see, this outfit is a really savvy pick, especially for summer-to-fall weather, when the mercury is dipping. Those who wonder how to wear cool off-duty dressing as you progress through your 20s, this outfit should answer your question.