For a goofproof relaxed option, you can't go wrong with this combo of a blue wool turtleneck and khaki chinos. Go off the beaten track and shake up your ensemble by finishing with a pair of navy leather low top sneakers. When temps are dipping and fall is settling in, you'll appreciate how perfect this getup is for summer-to-fall weather. Relaxed combos for stylish 30-something Millennial guys aren't actually that hard, as you see here.