If it's comfort and functionality that you're looking for in an ensemble, consider pairing a navy harrington jacket with brown chinos. If you wish to easily dial down this look with shoes, why not introduce a pair of high top sneakers to this look? So if you're scouting for a look that's seriously stylish but also feels entirely spring-appropriate, you found it. Casual outfits for stylish guys in their 40s aren't actually that hard, as you see here.