Go for a denim shirt and a crew-neck t-shirt to assemble an extra dapper and current casual outfit. With footwear, go for something on the relaxed end of the spectrum and finish your outfit with a pair of grey athletic shoes. When temps are starting to drop and autumn is in the air, you'll love this combination as your go-to for summer-to-fall weather. Think it's hard for over-40 men to perfect modern off-duty style? This pairing will prove you otherwise.