1. James Bond
Movies: James Bond franchise
Complex Says: Who else would be number one on this list other than James Bond? Bond is more than just tailored tuxedos and Brioni suits. His sportswear outfits show Bond's style versatility, and they always agree with the climate of the country he is sneaking through. Sean Connery's understated spy had all of Don Draper's swagger, George Lazenby infused a '60s mod sensibility in the character, and Daniel Craig brought him into the modern age, rocking white pants, desert boots, and herrington jackets when he wasn't in a perfectly tailored suit. Given his constantly ability to update his gear (and youth), there's no reason why James Bond shouldn't be the most stylish spy.