So as you can see, it doesn't take that much effort for a man to look casually smart. Pair a shirt jacket with a puffer jacket and be sure you'll look amazing. Dark brown leather casual boots provide comfort, but with a fashion effect. Seeing as the weather is getting chillier every day, this outfit seems a nice pick for the time in between seasons. As you're going from your 20s to your 30s, you want to start dressing more like a mature gentleman. If that's the case, looks like this are ideal as inspo.