An olive windbreaker and black chinos are an essential combo for many style-savvy gentlemen. Introduce a pair of black leather loafers to this ensemble for a touch of refinement. This ensemble is a nice pick when it comes to crafting a standout look for summer-to-fall weather. As you're getting to your 30s, you want to start dressing more professionally. That's when combos like this are a real life saver.