One of the smartest ways to style out such a hard-working menswear piece as a grey wool blazer is to pair it with grey wool dress pants. Spice up your look with a more relaxed kind of shoes, like this pair of dark green canvas low top sneakers. When leaves change color and autumn settles in, you'll love this outfit as your favorite for weird transition weather. Certainly a great option when it comes to outfit ideas for gentlemen in their sixties.