A shearling jacket and black skinny jeans are an easy way to inject effortless cool into your casual rotation. Want to dress it up in the footwear department? Complete your outfit with tan chelsea boots. When it comes to dressing for weird fall weather, nothing beats a knockout look that can take you from season to season. As you're going from your 20s to your 30s, you want to start dressing like a grown-up. If that's the case, combos like this are a real life saver.