Reach for a black denim jacket and a white and black horizontal striped crew-neck t-shirt for comfort dressing with a modernized spin. You could perhaps get a little creative on the shoe front and dial down your outfit by rocking black athletic shoes. When it comes to dressing for awkward fall weather, nothing beats a neat combo that can take you from season to season. This outfit illustrates that going from your 20s to your 30s is no reason to avoid casual clothing.