Effortlessly blurring the line between sharp and laid-back, this combination of a white bomber jacket and charcoal vertical striped chinos is sure to become one of your go-tos. When it comes to shoes, add a pair of white canvas low top sneakers to the equation. Nothing like a cool combination to spice up a gloomy fall day. This getup suggests how to keep succeeding in casual dressing as a 30-year-old gentleman.