![Grey Pants with Plaid Shirt Casual Winter Outfits For Men In Their 20s: Marry a plaid shirt with grey pants to assemble an interesting and contemporary outfit. Our favorite of a variety of ways to finish off this look is dark brown leather chelsea boots. In winter, when comfort is key, it can be easy to settle for a less-than-stylish outfit. However, this outfit is a practical illustration that you can actually stay comfortable and remain stylish at the same time during winter. Those who wonder how to pull off edgy off-duty style as you work your way through your 20s, this ensemble should answer your question.](https://cdn.lookastic.com/looks/shearling-jacket-long-sleeve-shirt-crew-neck-t-shirt-large-70364.jpg)
![Dark Brown Shearling Jacket](https://cdn.lookastic.com/dark-brown-shearling-jacket-original-10165591.jpg)
![Tan Plaid Long Sleeve Shirt](https://cdn.lookastic.com/tan-plaid-long-sleeve-shirt-original-3396479.jpg)
![White Crew-neck T-shirt](https://cdn.lookastic.com/white-crew-neck-t-shirt-original-386478.jpg)
![Grey Ripped Skinny Jeans](https://cdn.lookastic.com/grey-ripped-skinny-jeans-original-9154828.jpg)
![Dark Brown Leather Chelsea Boots](https://cdn.lookastic.com/dark-brown-leather-chelsea-boots-original-9659566.jpg)
![Black Sunglasses](https://cdn.lookastic.com/black-sunglasses-original-9639748.jpg)
Marry a plaid shirt with grey pants to assemble an interesting and contemporary outfit. Our favorite of a variety of ways to finish off this look is dark brown leather chelsea boots. In winter, when comfort is key, it can be easy to settle for a less-than-stylish outfit. However, this outfit is a practical illustration that you can actually stay comfortable and remain stylish at the same time during winter. Those who wonder how to pull off edgy off-duty style as you work your way through your 20s, this ensemble should answer your question.