This pairing of a white and navy vertical striped dress shirt and charcoal wool dress pants is seriously dapper and creates instant appeal. Let your sartorial credentials really shine by rounding off your getup with a pair of dark brown suede derby shoes. Can you see how extremely easy it is to look dapper and stay comfortable when chillier weather comes, all thanks to ensembles like this one? Nice and age-appropriate, a look like this will help outdo any of your younger pals.