When the occasion calls for an effortlessly smart ensemble, team a beige crew-neck sweater with a white dress shirt. A pair of black leather work boots will bring a playful feel to this ensemble. In the winter months, when functionality is key, it can be easy to settle for a less-than-stylish look in the name of convenience. However, this look is a striking example that you can actually stay comfy and remain stylish during the winter months. As you're going from your 20s to your 30s, you probably want to start dressing more professionally. That's when looks like this are a surefire option.