If you're looking to take your casual fashion game to a new level, dress in a black bomber jacket and a short sleeve shirt. To bring a bit of flair to your getup, complement your outfit with black chunky leather derby shoes. So as you can see, it's a neat, not to mention season-appropriate, getup to keep in your transitional wardrobe. This pairing is a huge inspo to anyone who had doubts about more sophisticated outfits in his 20s.