One of the smartest ways to style out such a hard-working menswear piece as a grey suit is to pair it with a white and navy vertical striped dress shirt. Brown leather tassel loafers tie the ensemble together. Seeing as autumn is taking over, this ensemble appears a wonderful idea for the transitional season. So if you're on a mission for outfit ideas on how to dress as you move into your 50s, this getup is a great example.