Marry a grey wool blazer with a black crew-neck sweater for a clean classy menswear style. In the shoe department, go for something on the dressier end of the spectrum by sporting a pair of black leather derby shoes. When you have one of those gloomy fall days, sometimes only a cool outfit like this one can get you to face the outside world. This is a good-looking but also age-appropriate combination for a 40-something gent.