We’ve all had that awkward moment. Strolling down the street, minding your own business, when suddenly you spot someone sporting a piece, a look, or well, a swagger that you must have for yourself. Darting across the street, risking life, limb, and just a bit of pride to grill said person on where, when, and for how much they obtained everything currently on their person isn’t the best look. Doing our part to alleviate this awkwardness, Gilt MAN has teamed with street style blog Swagger New York in creating a series of looks from three of Manhattan’s more style-conscious citizens, all shop-able from head to toe. Save those awkward encounters for another time.