Annie Hall (1977)

Annie Hall's menswear look (1977) Difficulty: very easy, and the best choice if you hate dressing up. Diane Keaton's character borrowed from the men's wardrobe: a man's tweed or check jacket, a pale shirt with a loosely knotted tie, a vest if you have one, and a soft wide-brimmed hat. Below, either baggy wide-legged pants or a long dark skirt with boots. Thrift store men's racks will cover every piece. Wear everything a little too big, because the oversized fit is what makes it read as Annie rather than office wear. A bit of nervous charm completes it.