When it comes to timeless refinement, this pairing of a black blazer and dress pants doesn't disappoint. Inject a playful vibe into this getup by slipping into a pair of charcoal desert boots. As the weather starts to improve, it's time to shed those bulky winter layers and choose an ensemble that's lighter, like this one here. As a 30-something Millennial man, you want to start dressing like an adult. In this case, combos like this are a tested option.