This off-duty pairing of a long sleeve shirt and black ripped skinny jeans is extremely easy to pull together without a second thought, helping you look awesome and prepared for anything without spending a ton of time rummaging through your closet. A pair of black slip-on sneakers immediately dials up the wow factor of any outfit. This look is a good option when it comes to planning a well-coordinated outfit for transeasonal weather. If you're often not sure how to dress as a guy in his 20s, this combo is a foolproof option.