This combo of a black vertical striped waistcoat and black jeans is really a statement-maker. On the shoe front, go for something on the relaxed end of the spectrum and round off your look with a pair of tobacco leather casual boots. Keep this look ready to go come warmer weather, and we promise you'll save a lot of time crafting what to wear on more than one occasion. If you frequently wonder how to dress age-appropriately but also look fashionable, this pairing is an amazing example.