A red and white plaid long sleeve shirt and a white crew-neck t-shirt are the kind of a fail-safe off-duty look that you need when you have no extra time to plan out an ensemble. Lift up this look with the help of dark brown leather casual boots. So as you can see, it's very easy to look seriously stylish and stay comfortable come cooler days, thanks to this look. This ensemble should clear any doubts you had about wearing casual clothes in your fifties.