For a look that's extremely easy but can be worn in many different ways, consider pairing a white windbreaker with charcoal chinos. A pair of white leather low top sneakers makes this look complete. This is a good illustration of how to dress with style as you progress through your 20s.
Putting together a white windbreaker with light blue jeans is a great idea for a laid-back outfit. Look at how well this getup pairs with white leather low top sneakers. Guys who are curious how to wear cool casual outfits in your mid-20s, you have your answer.