Why not dress in a crew-neck t-shirt and grey sports shorts? As well as totally functional, these two pieces look awesome when paired together. If you need to effortlessly up the style ante of this look with a pair of shoes, slip into beige canvas slip-on sneakers. There's no nicer way to cheer up a gloomy autumn day than a dapper look like this one. Now that's a fun look that's guaranteed to make you stand out among other middle-aged fellas.