You'll be surprised at how easy it is for any gentleman to get dressed this way. Just a black crew-neck sweater paired with navy jeans. You can get a bit experimental in the footwear department and complete your getup with black leather casual boots. On not-so-chilly days, you can wear a variation of this summer-to-autumn look and look absolutely amazing. This combo is a striking illustration over-50 guys can still very well turn heads.