Ah the classic jean jacket—it's the perennial favorite that has remained steadfastly (and reassuringly) constant amid fashion's cyclical current of trends. It's the perfect summer-to-fall (and jumping forward, even winter-to-spring) transitional piece. The denim outerwear has proven to be just warm enough for bitter breezes and chillier nights, and light enough to not overheat or stifle. And after what feels like the hundredth time re-purchasing the same item, we've (finally) learned to hold on to the topper despite impulsive de-cluttering sprees. This season, layer it over your beloved maxi dress or pair it with winter textiles, like tweed, for a cool-weather take. We took one jean jacket ($118; madewell.com) and created three different outfits—click through to see all the looks.