This relaxed combination of a black leather biker jacket and grey plaid chinos is super easy to pull together without a second thought, helping you look awesome and prepared for anything without spending too much time searching through your wardrobe. If you want to immediately dial up this look with shoes, complement your getup with a pair of black leather oxford shoes. This ensemble is an obvious choice when it comes to a killer summer-to-fall getup. A practical example for anyone who wonders how to dress as a guy in his twenties.