A navy waistcoat and navy chinos are the kind of effortlessly classy items that you can wear a great deal of ways. Here's how to spruce up this outfit: brown leather dress boots. As you can see here, it's extremely easy to look amazing and stay comfy when cooler weather hits, all thanks to getups like this one. Wondering what you should wear as you progress through your 20s? This combination is the perfect answer.