Repeat offender? Not a chance. When you invest in clothes that can work overtime—like these items—and become savvier about mixing and matching, no one will think you’re rehashing the same old styles. We’ve created five outfits from the pieces here, but you’ll undoubtedly find even more ways to combine them.
Button up the jacket and let the dress masquerade as a skirt. Top it off with the contrasting belt and black pumps for a finished look.
To buy: Talbots embossed-leather belt, $44, 800-825-2687. CC Corso Como black patent-leather heels, $149, corsocomoshoes.com.
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Go ahead and let that work blouse moonlight on the weekend. Make it seem less “officey” with the boyfriend cardigan, those anywhere-appropriate dark skinny jeans, a long pendant necklace, and a comfortable pair of flats. To buy: Freelook rose gold–plated steel watch, $200, freelookwatches.com. Lela Rose for Payless red faux-suede flats, $35, payless.com. J.Crew necklace.
4 of 6Perry Hagopian
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Feel free to mix prints. Just be sure that one is larger in scale than the other. Slip on the ladylike jacket and classic heels to keep the outfit from looking too quirky.
To buy: Sandy Hyun crystal-and-glass earrings, $60, 888-629-2456.
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Add layers to get more mileage out of a seemingly unforgettable item. Tone down the bold pattern of the dress with a solid cardigan and make it less recognizable. Then pair it with neutral shoes to keep the outfit looking subdued.
To buy: Nine West suede-and-leather heels, $99, ninewest.com.
6 of 6Perry Hagopian
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When in doubt, rely on tried-and-true combinations, like black and white. Wear the pants rolled up or down, and pair them with something unexpected, like brown platforms and a rust bag. Layer on jewelry—chain necklace, watch, cocktail ring—to pump up the luxe look.
To buy: Jaeger suede-and-leather bag, $390, jaeger.co.uk. Monet glass-pearl cocktail ring, $42, 800-289-6229. Sequin gold-plated chain necklace, $78, 212-398-7363.