The idea of a day dress doesn’t— and has never—existed in my wardrobe. Oh, but they’re so easy, everyone says: Slip it on, and off you go! But what shoes? Tights, or bare-legged? What underwear— and then what on earth goes over the top? A cardigan seems trite. A jacket? Sure, but what kind of jacket? Once you’ve overcome those challenges, you have to adhere to some basic behavioral codes, like how to sit upright, with legs crossed. (You certainly can’t sit slouched in a chair or with your legs remotely apart.) Frankly, it’s a minefield—and one that, yes, even as a Vogue editor, I’ve never had the patience nor the desire to navigate.
Tailoring, on the other hand, makes a whole lot of sense: A two-piece solution that works for anything, anywhere, in any season, where the only decision required is whether to wear it with a white T-shirt or a white shirt (or, perhaps, with nothing at all). I’ve always loved an oversized shape with roomy, mannish pleat-front trousers that sit low on the waist and pool a little—the hems scrunching up over chunky flat boots while also long enough to accommodate a heel—and I lean toward a shoulder line so broad that it announces your arrival into a room a good while before the rest of yourself slips in.
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