If you don't take fashion too seriously, go for a bold casual look in a tobacco shearling coat and black ripped skinny jeans. Go down a classier route on the shoe front by sporting a pair of beige suede chelsea boots. While it can be a bit nerve-racking and time consuming to look stylish on extra cold days, it's combos like this that prove it's totally possible. Those wondering how to wear edgy casual style as you work your way through your 20s, you have your answer.