If you're scouting for a laid-back and at the same time sharp look, consider teaming a grey long sleeve t-shirt with charcoal ripped jeans. If you're hesitant about how to finish off, a pair of black leather work boots is a nice choice. As you can see, this outfit is a really savvy pick, especially for awkward fall weather, when the mercury is falling. Those who wonder how to wear cool casual dressing as you navigate your 20s, this combination should answer your question.