The varsity jacket is one of those pieces you either feel immediately comfortable in or you spend the entire time wearing it wondering if you look like you’ve wandered out of an American high school from 1987. We’ve been in both camps at different points. The key we’ve found is to treat it as a casual piece without any additional self consciousness about what it’s referencing culturally. A clean varsity with wool body and leather sleeves in navy or black worn with simple jeans and a plain tee looks genuinely great. The mistake is overthinking the references and either doubling down on the Americana theme with everything else or trying to dress it down so much that you’re fighting against the jacket rather than working with it. Keep everything else quiet and let the jacket be what it is.