For a look that's very easy but can be flaunted in a multitude of different ways, reach for a white and red crew-neck t-shirt and jeans. Go ahead and introduce a pair of black leather brogue boots to the mix for an extra touch of refinement. You can see this ensemble is also a great illustration of how to dress stylishly in the dead of winter. Wondering what to wear as you step into your 50s? This getup is a wonderful example.