For a laid-back and cool outfit, reach for a grey crew-neck sweater and black jeans — these items work perfectly well together. Add a pair of black suede desert boots to this outfit for extra style points. During winter, when warmth is a must, it can be easy to settle for a less-than-stylish outfit. However, this outfit is a striking illustration that you totally can stay toasty and remain stylish in winter. When it comes to casual clothing for 20-something gentlemen, this combination looks cool on almost any man.