Go for a simple but at the same time laid-back and cool look by wearing a v-neck sweater and a white long sleeve shirt. When in doubt about what to wear when it comes to shoes, complement your outfit with brown leather desert boots. With a look like this in your winter wardrobe, you're guaranteed to keep warm and look awesome despite the nasty weather. This combination demonstrates that in your mid-20s your sartorial options are far from limited.