This combo of a blue denim jacket and a white print crew-neck t-shirt is proof that a safe casual look doesn't have to be boring. You can take a more laid-back approach with footwear and add a pair of black athletic shoes to the equation. When temps are starting to drop and fall is in full swing, you'll love this ensemble as your go-to for in-between weather. When it comes to casual dressing ideas for middle-aged gentlemen, this combination is perfect.