For an outfit that's extremely easy but can be worn in many different ways, rock a multi colored plaid long sleeve shirt with a white crew-neck t-shirt. Add navy suede loafers to this look to instantly step up the classy factor of any ensemble. When you have one of those gloomy fall days, sometimes only a killer look like this one can get you to face the outside world. This outfit illustrates that looking fashionable as a middle-aged gent is easier than one might think.