A white and blue vertical striped dress shirt and a dark brown raincoat are among the key items in any modern gent's great wardrobe. Feeling experimental today? Spice up this look by sporting a pair of dark brown leather tassel loafers. Seeing as fall is setting in, this ensemble appears a viable idea for the time in between seasons. If you're wondering how you should dress as a man in his fifties, this pairing gives a proper idea.