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I didn't do any clubs while there last summer but Big in Japan and Plan B are worth a trip for drinks.
Born and raised in Montreal, the underground mall is basically filled with stuff you can find anywhere.
If youre looking for clothing :Uomo on Peel sells the high end staples, borelli, corneliani, isaiah, kiton etc. (John Lobb and Edward Greens too only place in the city)
Clusier is mid range (Samuelsohn at around 1400-1600, sell some carminas)
or Giorgio is more off the beaten path kind of italian flair.
Also check out Rooney's in the old port.
For clubbing/night out:
Buonanotte is always fun but packed, across the street is Globe which is nice, Big in Japan, Maccaroni bar/Candy bar/Pink Taco
Food:
Great restaurant called Lemeac, its on Laurier, after 10 special cant be beat at night (french bistro)
Garde Manger/Pied de Cochon/Joe Beef really are fantastic if youre in old montreal try to go to Le Club Chasse et Peche also really good (or a place called Mythos is very popular, great resto upstairs clubbing downstairs, greek food). Let me know if you need any more info.