This combo of a navy henley sweater and black jeans is a safe go-to for an effortlessly stylish outfit. Go off the beaten track and break up your ensemble by rocking chelsea boots. This look is the definition of ideal for when temps are starting to drop and autumn is settling in. As a gent in his 30s, you probably want to start dressing like a grown-up. That's when outfits like this are a lifesaver.