For a look that's super straightforward but can be smartened up or dressed down in plenty of different ways, wear a navy double breasted blazer and white chinos. On the shoe front, go for something on the smarter end of the spectrum and complete this look with a pair of tobacco leather monks. So as you can see, this combo is a really good idea, especially for weird fall weather, when the temps are dropping. Gents wondering how to rock semi-casual dressing as you cruise through your 20s, you have your answer.