A brown shearling jacket and charcoal jeans make for the ultimate laid-back style for any modern gentleman. If you need to instantly dress down your ensemble with footwear, why not choose a pair of black leather low top sneakers? This getup is a stark illustration you can still outfit dapper while bundled up. Guys who are curious how to wear cool casual outfits as you work your way through your 20s, you have your answer.