For a laid-back and cool outfit, dress in a v-neck t-shirt and blue jeans — these pieces work beautifully together. Don't know how to complete this ensemble? Rock a pair of white leather oxford shoes to smarten it up. A great example of comfortable style, this ensemble must be in your front hall closet when the cold days hit. So if you're on a mission for fashion inspiration for dressing as you head into your 50s, this outfit is a great example.