One of the coolest ways for a man to style out a black long sleeve shirt is to pair it with navy jeans in a relaxed casual look. Brogue boots are a fail-safe way to breathe an added touch of style into this look. When it's one of those gloomy fall days, what better to cheer it up than a stylish outfit like this one? So if you need style inspiration for dressing as you pass the big six-oh, this outfit is perfect.