One of the best ways for a man to style an olive military jacket is to marry it with jeans in a casual look. Rounding off with tobacco high top sneakers is an easy way to add a more casual aesthetic to this outfit. As you can see here, this ensemble is a really smart idea, especially for summer-to-fall weather, when the temperatures are starting to drop. Think you can't pull off edgy off-duty dressing as you get into your 50s? This combo will prove you wrong.