You'll be amazed at how easy it is for any man to pull together this off-duty ensemble. Just a brown military jacket and chinos. If you want to feel a bit fancier now, complete this outfit with dark brown leather loafers. As you can see here, this getup is a really good pick, especially for transeasonal weather, when the temperature is dropping. Wondering how you should dress as you age into your 50s? This outfit is the perfect answer.