For an outfit that's pared-down but can be worn in plenty of different ways, try pairing a grey bomber jacket with black jeans. Feeling brave today? Switch up your outfit with a pair of black leather derby shoes. So as you can see here, it's a stylish, not to mention season-appropriate, getup to have in your transitional rotation. A good source of inspiration for 20-something guys aiming to move their style towards maturity.