So as you can see, it doesn't require that much effort for a man to look effortlessly sleek. Marry a brown check blazer with white chinos and you'll look incredibly stylish. The whole ensemble comes together quite nicely if you introduce a pair of dark brown leather desert boots to the equation. Seeing as temperatures are dropping, this getup appears a viable pick for in between seasons. When it comes to fashion for gents in their fifties, this getup is ideal.