A waistcoat and a black and white dress shirt are absolute mainstays if you're piecing together a smart wardrobe that holds to the highest menswear standards. To give your overall ensemble a more relaxed twist, why not complete your outfit with a pair of black suede tassel loafers? Seeing as fall is taking over, this outfit is a viable idea for the time in between seasons. Those who are curious how to dress with style as you move into your 50s, you have your answer.