For an ensemble that's pared-down but can be dressed up or down in a great deal of different ways, make a blue plaid overcoat and blue jeans your outfit choice. Rounding off with black leather derby shoes is the most effective way to inject an added touch of sophistication into this look. This one is a viable pick if you're picking out a knockout look that transitions easily into fall. If you're often not sure how to dress as a gentleman in his 20s, this ensemble is a wonderful example.