This laid-back combination of a military jacket and a crew-neck t-shirt is extremely easy to pull together without a second thought, helping you look dapper and ready for anything without spending too much time searching through your wardrobe. When it comes to shoes, this look pairs really well with white canvas low top sneakers. As you can see, it's very easy to look awesome and stay comfy come colder days, thanks to this outfit. This outfit is a striking example middle-aged men can still very well turn heads.