A charcoal double breasted blazer and blue jeans married together are the perfect combo for those dressers who prefer casually classic combos. Want to go all out on the shoe front? Add a pair of dark brown leather tassel loafers to the mix. This one is a viable pick when it comes to picking out a standout outfit for summer-to-fall weather. This ensemble demonstrates how to look stylish as you step into your 50s.