If you gravitate towards casual combinations, why not opt for a black and white blazer and jeans? And if you want to instantly kick up this look with one single piece, throw tobacco leather derby shoes in the mix. It's a smart idea when it comes to picking out a standout outfit for summer-to-fall weather. If you're not sure how to dress appropriately for your age but also look fashionable at 60, this outfit is a great example.