The Windy City
‍The Windbreaker, Dressed Up
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Sometimes you have to break the rules.
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The windbreaker? She’s breaking out of her box this fall—moving from the gym to out on the town. And she’s owning it.
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The most worn item in my closet right now? The Row’s black windbreaker. I got her on sale last year, and she’s amazing. My weekend go-to. Fabulous with leggings. Cute with cuffed denim or cutoff shorts. The hood earns its keep on rainy days—and this summer there have been many. Barely a week goes by that I don’t take her for a spin.

But what if—for a novel idea—I were to pair her with my favorite white tee (currently the Leset Margo) and a pencil skirt? Or what if she makes a debut with High Sport Kick Pant and a Repetto ballet flat? I’m leaning in.

And now that I’ve started… well, no surprise. My Row jacket? She wants friends. Who am I to deny her? I’m dreaming of Saint Laurent’s khaki canvas funnel neck. Paired with Alfie Paris’ black tube skirt and a pair of Manolo slides? Chef’s kiss.
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The beauty of a windbreaker? You don’t need to buy a new outfit to accessorize her. Break the mold and pair her with polished pieces that are already hanging in your closet—a black pencil skirt, black kick-flare trousers, satin pants, a mini skirt, your favorite tee, a simple mule or pointed-toe kitten heel, and you’re ready to hit the town.
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Nylon and diamonds? Yes, please. Say less. Accessories are the easiest way to add a little sparkle to your tech jacket.

And maybe that’s the point. The windbreaker doesn’t need a new identity. She just needed better company.