A beige zip sweater and khaki chinos matched together are a match made in heaven for guys who prefer relaxed casual styles. Give an element of sophistication to this look with dark brown suede loafers. When it comes to dressing for awkward transition weather, nothing beats a cool combination that will keep you snug and looking your best. So if you're looking for outfit inspiration for dressing as you step into your 50s, this ensemble is perfect.