This combo of a navy quilted gilet and a grey long sleeve t-shirt is very easy to do and so comfortable to wear as well! Rounding off with a pair of brown suede chelsea boots is a simple way to introduce a bit of depth to your look. As days are getting cooler, you'll find that an outfit like this is perfect for the season. This combination illustrates that dressing stylishly as an over-40 gentleman is not that daunting a task.