Jumpsuits are more grown-up than a pair of overalls but offer a relaxed alternative to dresses. Topshop jumpsuit, $115, Hudson's Bay; Shoes, US$390, Tommy Hilfiger; Bag, $90, Zara; Necklace, $125, Jenny Bird.
A waistline that meets your own — or reaches a bit higher — is fitting for every shape. J Brand jeans, $268, Neiman Marcus; Topshop top, $80, Hudson's Bay; Bag, $50, earrings, $18, Zara.
The Canadian tuxedo is no longer a fashion don’t. To make it work for you, pick a top and bottom in contrasting washes (like pale blue with deep indigo). Denim shirt, $50, Winners; Houndstooth bag, $40, ALDO; Ring, $10, Le Chateau; Elizabeth and James jeans, $385, Shopbop.
Your pant leg can be rolled, scrunched, folded or cuffed whether you're going for clean and casual or slightly asymmetrical. From clockwise: Jeans, $210, Fidelity Denim. Boots, $280, Winners; The Castings jeans, $225, Aritzia; 501 CT jeans, $108, Levi's; 711 jeans, $99, Levi's.
Because your black trousers deserve a break. Jeans, $188, Fidelity Denim; Top, $135, Michael Kors; Iro jacket, $795, TNT; Boots, US$490, Tommy Hilfiger; Ring, $13, belt, $25, Le Chateau.
Your grade two photo this is not. Rag & Bone skirt, $500, Holt Renfrew; Shirt, $46, boots, $139, Zara; Necklace, $12, ALDO.
Brightly coloured washes and prints have fashion clout, but you’ll get the most wear out of tried-and-true blue.
Cuffed slouchy jeans call for a pretty pump and a bare ankle — or create a long line with hidden platforms and a hemline that just grazes the floor. Sneakers pair best with skinnies, of course. From clockwise: Sam Edelman, $210, Shoe Boutique; Sam Edelman, $160, Shoe Boutique; Converse, $65, SoftMoc; Shoes, $140, Nine West.
Welcome to the new milennium, bell-bottoms! Frame jeans, $295, TNT; Topshop blazer, $110, Hudson's Bay; Chloé bag, $550, TNT; Shoes, $525, Michael Kors.
Makeup and hair: Claudine Baltazar; Styling: Fiona Green.
Related:
Cozy, Canada-proof boots you’ll need this winter
12 chic parkas to keep you warm this winter
Our foolproof guide to handbag terminology
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