Opt for a black long sleeve shirt and black jeans, if you prefer to dress for comfort without looking like a slob to look stylish. Black slip-on sneakers integrate seamlessly within a ton of ensembles. Seeing as it is getting colder with each day, this ensemble seems a smart option for the time in between seasons. Men who wonder how to wear modern casual outfits in your late 20s, this pairing should answer your question.