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Storyline (warning: spoilers)
The Outfit through a gradually thickening plot that rarely shows its seams is a maze like puzzle of a film, one that swiftly invites the audience in for an involved round of Cluedo unraveling inside an intimate, handsomely smoky Chicago outfitter dressing its wealthy clientele in the 1950s. The master behind the small yet exclusive bespoke is Leonard Burling , a Savile Row-trained cutter who’s left his London home for The States after the WWII. The Nazis were obviously the chief reason for his departure; blue jeans (even though they weren’t quite an established thing then) that threatened to put him out of business, as he says, was another. But the maestro sartor found his groove back in his Windy City atelier against the odds, after some secret tragedy. As long as you don’t call him a tailor—what is he, someone who just hems trousers and fixes buttons?—and refer to him accurately as a cutter, all will be well.
But it doesn’t take long for us to realise that the old artisan is mixed up with a lot more than stitches and cutting patterns. Gangsters, particularly the Boyle family—Simon Russell Beale’s seemingly temperate boss Roy, his spoiled son Richie (Dylan O’Brien) and their inside men Francis (Johnny Flynn) and Monk (Alan Mehdizadeh)—populate his joint frequently, using his workshop as a safe communication hub to drop messages for their crime family members.
If only all could stay as smooth and operational as the film’s opening act. But as the pieces trickle in over the course of a day or so, we find out about a rivaling crime family, an elite crime organisation called “the outfit” that Boyles want to become a part of as well as a possible rat, recording incriminating conversations on a cassette and passing them onto the FBI. What could possibly go wrong when things like murder, money and romantic stakes are involved? Part of the fun of The Outfit is its continually self-renewing demeanour that will keep the viewers guessing until its final moment. In the end, you leave The Outfit feeling like you have seen something rich, ravishing, and sumptuous.