This city casual pairing of a red and black long sleeve shirt and light blue ripped jeans is very easy to put together without a second thought, helping you look sharp and ready for anything without spending a ton of time combing through your wardrobe. If in doubt as to what to wear in the footwear department, stick to a pair of high top sneakers. Men who are curious how to rock edgy off-duty outfits in your late 20s, this combination should answer your question.