For an outfit that's very simple but can be flaunted in a multitude of different ways, dress in a blue houndstooth blazer and a navy crew-neck t-shirt. Spice up this look with a more polished kind of shoes, such as this pair of black leather chelsea boots. This one is a viable idea if you're crafting a standout ensemble for unpredictable fall weather. If you often wonder how to dress age-appropriately, this combination is a never-failing option.