This combination of a grey houndstooth overcoat and navy linen chinos falls somewhere between dressy and relaxed. Feeling bold today? Spice up your getup by rounding off with a pair of dark brown suede derby shoes. When temps are dropping and fall is settling in, you'll love this combination as your favorite for awkward transition weather. A practical example for any gent who's not sure how to dress as a 50-something man.