Effortlessly blurring the line between sharp and relaxed casual, this combination of a navy hoodie and teal chinos can easily become one of your favorites. Complete your ensemble with a pair of oxford shoes for a masculine aesthetic. On not-so-chilly days, you can wear a variation of this summer-to-fall outfit and look absolutely amazing. Wondering how to dress your age as you head into your 40s? This combination is a vivid example.