Combining a grey plaid suit and a multi colored gingham dress shirt is a fail-safe way to infuse your wardrobe with some rugged elegance. Get a little creative on the shoe front and add a pair of violet print canvas low top sneakers to the mix. Stick with this one if you're hunting for a cool summertime getup. So as you can see, as an over-40 man, you have a wide array of style options.