If you gravitate towards relaxed style, why not wear this combination of a military jacket and a crew-neck sweater? A pair of white canvas low top sneakers will easily dress down a polished look. Perfect if you're looking for some seriously inspiring style for 50-something gentlemen.
Try pairing a military jacket with a crew-neck sweater if you're aiming for a proper, stylish outfit. You could perhaps get a little creative with shoes and add a pair of navy canvas low top sneakers to the equation. Off-duty combinations for stylish middle-aged gentlemen aren't actually that hard, as you can see here.