This casual street style pairing of a charcoal wool blazer and navy ripped skinny jeans is extremely easy to put together without a second thought, helping you look seriously stylish and prepared for anything without spending too much time rummaging through your wardrobe. For something more on the dressier end to finish your look, add a pair of black leather derby shoes. It's a great pick if you're picking out a standout ensemble for in-between weather. Guys who wonder how to pull off cool casual dressing as you get into your 30s, this ensemble should answer your question.