This ensemble with a waistcoat and grey sweatpants isn't so hard to achieve and leaves room to more creative experimentation. If you want to immediately smarten up your look with footwear, introduce a pair of black leather derby shoes to the equation. Rest assured, this look will keep you toasty as well as looking stylish in this unpredictable fall weather. As you're maturing from your 20s to your 30s, you want to start dressing like a grown man. If that's the case, combinations like this are a life saver.