On days when comfort is everything, this combo of a black leather biker jacket and a red and black plaid flannel long sleeve shirt is a no-brainer. For something more on the dressier side to finish off your outfit, introduce a pair of dark brown leather casual boots to the equation. This one is a savvy pick when it comes to picking out a knockout look for weird fall weather. Think 50-year-old guys can't pull off cool casual style? This combo is indisputable proof of otherwise.