For relaxed dressing with an urban spin, marry a navy hoodie with navy jeans. Go the extra mile and shake up your outfit by finishing off with brown leather chelsea boots. In the winter season, when warmth is a must, it can be easy to surrender to a less-than-stylish ensemble. But this ensemble is a stark illustration that you can actually stay toasty and remain stylish in the winter season. When it comes to casual outfit ideas for 20-something men, this combo looks great on almost any gentleman.