A white crew-neck sweater and skinny jeans will give off this casually cool vibe. In the shoe department, go for something on the more elegant end of the spectrum and complement your getup with a pair of beige suede chelsea boots. If you're in search of a cool winter-to-spring look, look no further. As you're going through your late 20s, you want to start dressing more like a mature gentleman. That's when inspiration like this proves very useful.