For an outfit that's smart and GQ-worthy, try teaming a grey blazer with grey wool dress pants. If you wish to easily dial down your ensemble with a pair of shoes, why not make brogue boots your footwear choice? If it's one of those dull autumn days, what better to brighten it up than a sharp look like this one? When it comes to dressing ideas for 50-year-old gents, this combo looks great on almost any gent.