A black leather biker jacket and a black cable sweater are an easy way to introduce subtle dapperness into your casual rotation. Finishing off with a pair of dark brown suede chelsea boots is an easy way to infuse an extra dose of elegance into this look. This one is a viable choice when it comes to putting together a standout ensemble for summer-to-fall weather. Those wondering how to rock classic and casual outfits as you move through your 20s, you have your answer.