This look clearly illustrates it is totally worth investing in such timeless menswear items as a tan gingham blazer and grey wool dress pants. When not sure about the footwear, rock a pair of dark brown suede tassel loafers. This combo is a great choice if you're figuring out a standout outfit for summer-to-fall weather. Just because you've passed the big 4-0, doesn't mean you're allowed to give up on fashion, and this outfit proves exactly that.