Dress to impress in a charcoal three piece suit and a light blue dress shirt. Dark brown leather derby shoes will add a dash of stylish effortlessness to an otherwise all-too-safe look. As you can see here, this combo is a really wonderful idea, especially for awkward transition weather, when the temperatures are dipping. So if you're in search of fashion inspo for dressing as you step into your 50s, this combo is perfect.