So as you can see, it doesn't require that much effort for a man to look effortlessly neat. Just make a burgundy sweater vest and navy chinos your outfit choice and you'll look amazing. Don't know how to finish? Grab a pair of black leather low top sneakers to shake things up. When you have one of those bleak fall days, sometimes only a killer look like this one can get you to face the outside world. Those wondering how to pull off smart dressing as you drift through your 20s, this outfit should answer your question.