As you can see here, looking casually sleek doesn't take that much effort. Just make a hoodie and a dress shirt your outfit choice and be sure you'll look awesome. Spice up your outfit by rounding off with a pair of navy leather loafers. This getup is a good option if you're putting together a killer ensemble that will take you from summer to fall. So if you're on the hunt for dressing tips for 50-something guys, this pairing is definitely worth saving for later.