Pair a crew-neck t-shirt with black skinny jeans if you're after an outfit idea for when you want to look casually dapper. You can get a little creative in the shoe department and spruce up this getup by sporting black suede chelsea boots. So as you can see, this look is a really great pick, especially for transeasonal weather, when the temperatures are starting to drop. Wondering how to master casual style as you pass the big 4-0? This combination is the perfect answer.