For a laid-back and cool ensemble, try pairing a black hoodie with a black and white vertical striped long sleeve shirt — these items fit really nice together. Bump up the classiness of this look a bit by slipping into a pair of tan suede derby shoes. As you're transitioning from your 20s to your 30s, you probably want to start dressing like a grown-up. In this case, outfits like this are a fail-safe option.