You'll be surprised at how easy it is for any man to get dressed this way. Just a navy hoodie married with cargo pants. A pair of white canvas low top sneakers will be a stylish addition for this ensemble. When you have one of those gloomy fall days, sometimes only a neat look like this one can get you out the door in the morning. Guys who are curious how to dress stylishly as you pass the big four-oh, you have your answer.