When the setting allows off-duty dressing, consider pairing a black camouflage puffer jacket with black sweatpants. Does this outfit feel all-too-polished? Let a pair of black leather high top sneakers switch things up. Can you see how super easy it is to look stylish and stay toasty when colder weather hits, all thanks to ensembles like this? This getup shows how to dress fashionably and look good in your 20s.