A white and black dress shirt and blue ripped jeans worn together are a match made in heaven for guys who appreciate cool and casual styles. Change up your outfit with desert boots. In winter, when comfort is essential, it can be easy to settle for a less-than-stylish outfit. But this outfit is a stark illustration that you totally can stay toasty and remain stylish in winter. This ensemble suggests how to look stylish as you progress through your 20s.