This outfit demonstrates that it pays to invest in such timeless menswear pieces as a charcoal vertical striped suit and a white dress shirt. When in doubt about what to wear in the footwear department, stick to black leather oxford shoes. Clearly, it's easier to work through a blazing hot hot weather day in a cool outfit like this one. Good-looking and age-appropriate for a guy in his twenties, an outfit like this will help upstage any of your peers.