For a cool and relaxed getup, try pairing an olive crew-neck sweater with grey chinos — these two items go nicely together. The whole getup comes together when you introduce brown leather desert boots to the mix. During the colder months, when warmth is paramount, it can be easy to settle for a less-than-stylish outfit in the name of convenience. But this outfit is a striking illustration that you totally can stay cozy and remain stylish at the same time in the colder months. Those who wonder whether you can still sport edgy casual outfits as you step into your 50s, you have your answer.