As you can see, looking casually sleek doesn't take that much work. Pair an overcoat with a grey hoodie and be sure you'll look amazing. Black athletic shoes are an effortless way to infuse a sense of stylish casualness into your getup. Can you see how very easy it is to look on-trend and stay toasty when chillier days are here, all thanks to getups like this? Those wondering how to rock cool casual looks as you progress through your 20s, this combo should answer your question.