Go all out in a charcoal suit and a dress shirt. As for the shoes, take a more casual route with brown leather derby shoes. A killer summer-to-fall getup like this one makes it very easy to embrace the new season. This is a great illustration of how to dress stylishly and look age-appropriate.
Teaming a charcoal suit and a dress shirt is a guaranteed way to infuse your closet with some masculine refinement. A pair of brown leather derby shoes introduces just the right amount of visual interest to this outfit. This combo is a wonderful pick if you're figuring out a well-coordinated outfit for weird transition weather. Dressed like this, any middle-aged gent is guaranteed to put any younger dude to shame.