This combo of a white and navy horizontal striped crew-neck t-shirt and olive chinos is on the casual side but will guarantee that you look stylish and extra sharp. Breathe a sense of elegance into this look by rocking a pair of tobacco leather loafers. Totally appropriate for hot summer afternoons, you can wear a variation of this ensemble all season long. Wondering how to dress appropriately for your age after fifty? This outfit is the perfect answer.