This off-duty pairing of an overcoat and black skinny jeans is very easy to pull together without a second thought, helping you look amazing and prepared for anything without spending a ton of time digging through your wardrobe. A pair of tobacco work boots easily ramps up the appeal of your look. We love how ideal this one is for weird transition weather. Guys who wonder how to pull off cool casual outfits as you make it through your 20s, you have your answer.