This combination of a black crew-neck t-shirt and grey chinos is incredibly stylish and yet it looks practical and ready for anything. In the shoe department, go for something on the more elegant end of the spectrum and finish off your look with monks. As you can see here, this look is a really savvy idea, especially for transeasonal weather, when the temps are starting to drop. So if you need outfit inspo for dressing as you step into your 50s, this getup is perfect.