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These three women were tired of their shoulder-length hair

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Before: A self-professed ‘hair chameleon,’ Sarah Magwood, the owner of Magwood, a vintage-couture boutique in Toronto, has over the years sported every length, style and colour, and she has never been afraid going short. This fall, however, Magwood wanted a focused, modern cut. ‘I live in vintage clothes,’ she explains, ‘so I want something that won’t make me look costumey.’ 1960s hand-beaded top, 1980s rhinestone floral earrings, model’s own.

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After: To take Magwood’s shoulder-length locks from demure to daring, Chanel Croker, owner of Day and Night salon in Toronto, created a modified 1920s bob reminiscent of Audrey Hepburn’s hairstyle in Roman Holiday. ‘I love the flapper look and the idea of effortless femininity, but I wanted to give it an urban spin,’ says Croker, who updated the geometry of Vidal Sassoon’s iconic five-point cut with a looser shape, a subtler wedge and sweeping bangs. While this look carries all the focus that Magwood desired, a short bob like this one is nevertheless versatile and requires little more than the right tools to be transformed. As Croker points out, ‘With short hair, you really get to experiment with products that would make long hair greasy or weighed down.’ She recommends using a styling cream to slick hair back for a polished Tilda Swinton effect or apply a volumizing mousse on the front section to create a pompadour worthy of Janelle Monáe. Magwood, for one, plans to conscript dangling earrings from the 1920s to complement the look, along with another undeniably sexy accessory: “the nape of the neck.” 1960s mini-skirt, 1960s cropped jacket, 1970s fox-fur collar, model’s own.

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Before: ‘I still want to feel feminine and be able to pull my hair back,’ Kate Makinson, a public-relations pro at Narrative PR, says as she protectively sweeps her long blond waves into a ponytail. Three years ago, she explains, she dyed her hair black and had it chopped into a Victoria Beckham-inspired pixie, a hairstyle she refers to as ‘the worst decision’ of her life. Helmut Lang white knit top, $245 at Holt Renfrew, Kessa cobalt and gold necklace, $20 at Aldo.

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After: ‘Chopping off your hair, especially when you’ve never had short hair, is like getting rid of your security blanket,’ Croker says. ‘Women feel exposed and that’s really intimidating.’ Makinson couldn’t agree more. ‘It’s amazing what you can hide behind long waves,’ she laughs. ‘But I want something that’s refined and edgy now and am in a place where, emotionally, I can pull it off.’ For a longish-meets-short effect, Croker created a long bob, or a ‘lob’, with layers that fall between the chin and collarbone to frame the face and work with the fine texture of Makinson’s hair. The wash-and-go style works with thick hair, too, though for Makinson, Croker added short layers all around the head to enhance her natural wave and create volume and lift. The less-is-more style looks best when it’s slightly rumpled, Croker notes – a boon for anyone with a high-paced work life like Makinson’s. A mist of salt spray and some finger combing is all the maintenance required. Kenzo printed sweater, $440, J. Brand leather pants, $1,299 at Holt Renfrew.

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Before: The mussy signature bob of supermodel Karlie Kloss inspired plenty of women to cut their hair short this year, including Erika Brodsky, owner of vintage store Sub Rosa on Kensington Avenue in Toronto. Earlier this year, Croker cut Brodsky’s waist-length mane into a modified, shoulder-length version of the style. Now, after adjusting to short waves, Brodsky was ready to fully commit to the Kloss. “I had to [do it] in stages so I wouldn’t go into shock,” she says. Wild Thing shirt, $22, Silver Queen earrings, $24 at Sub Rosa Vintage.

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Dubbed the new Rachel, the Karlie is the brainchild of the hairstylist Garren Defazio and echoes the signature boho style of Jane Birkin in the 1960s. It hovers just below the chin and features long layers and bangs that sweep across the forehead. ‘This style feels airy because of the light layering around the perimeter,’ explains Croker and adds that, while the style works equally well on both fine and thickly textured hair, women with the latter should ask for a cut that creates volume at the sides of the head, not the crown, to avoid the mushroom effect. Regardless of hair type, she concludes, ditch the dryer. This style is freshest, and most fetching, when it’s slightly dishevelled. Schoolboy shirt, $18, mini smock dress, $34, 19702 leather biker jacket, $129, leather and brass belt, $28, at Sub Rosa Vintage.

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