A charcoal houndstooth blazer and navy skinny jeans teamed together are a match made in heaven for those dressers who prefer neat and relaxed combos. Finishing off with brown suede chelsea boots is a simple way to introduce some extra definition to your look. On not-so-chilly afternoons, you can rock a version of this easy-to-transition look and look absolutely amazing. Scouting for dressing ideas for 20-something men? This getup is pretty inspiring.