If you feel more confident wearing something functional, you'll appreciate this on-trend combo of a bomber jacket and a navy v-neck sweater. Black leather chelsea boots are guaranteed to breathe an added touch of style into this look. On not-so-chilly days, rock this summer-to-fall ensemble and look absolutely awesome. As a man in his thirties, you probably want to start dressing maturely. In this case, inspiration like this is very useful.