Pairing a navy waistcoat with navy and green plaid dress pants is an on-point choice for a stylish and classy ensemble. Go the extra mile and break up your ensemble by rounding off with white canvas low top sneakers. On not so cold days, you can wear a variation of this transitional outfit and look absolutely amazing. Wear this combo to look like a well-dressed a 60-something that you are, rather than a depressed retiree.