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Red Reddington (James Spader), The Blacklist
The criminal mastermind is known to rock a debonair three-piece suit, but it's his various fedoras that really, shall we say, top off the outfit. His dark ensembles add to his old-school brand of intrigue, but also make him look pretty bada-- while taking down The Blacklisters. Intimidating, powerful and impeccably groomed. What else do you expect from the self-styled Concierge of Crime?