Why not dress in a white crew-neck t-shirt and dark green sweatpants? As well as super comfortable, these two pieces look amazing worn together. As for shoes, introduce a pair of white athletic shoes to the equation. This getup is a viable choice when it comes to a killer getup that transitions easily into fall. Gentlemen wondering how to pull off edgy casual outfits as you make it through your 20s, you have your answer.