This pairing of a navy quilted gilet and grey vertical striped chinos is indisputable proof that a simple off-duty look doesn't have to be boring. Serve a little mix-and-match magic by finishing off with dark brown leather double monks. You can bet this outfit will become your uniform come chillier weather. As a 30-something Millennial man, you probably want to start dressing like a grown-up. If that's the case, ensembles like this are ideal as inspo.