This refined combo of a white check dress shirt and grey wool dress pants is a popular choice among the sartorially superior gents. On the shoe front, this ensemble pairs well with dark brown leather loafers. Keep this outfit in your front hall closet come warmer weather, and we guarantee you'll save time racking your brain for what to wear on more than one occasion. Searching for dressing tips for middle-aged gents? This pairing is great inspo.