How to Match Plaid With Plaid Like an Instagram Style Star

Observe: opposite sizes, opposite patterns, opposite everything. "A larger, simpler windowpane print in a neutral shade works well against a smaller, busier print in a more dominant color," Duprie says. "Keep everything else monochromatic and muted—the plaids are the stars here."

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You can't go wrong with white-accented black on black (on black on black). It's eternally chic—even when the prints aren't identical. The key? Commit to wearing ebony from head to toe. "Plaid can feel a bit too casual and underdressed," Duprie says. "An all-black base elevates the entire look to dressy and sophisticated."

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Work within a similarly scaled plaid palette that consists of three colors, Duprie advises. Exhibit A: Duprie's shirt and pants are navy with taupe lines, while the cape is taupe with cream plaid lines. "Always look closely at the weakest shades in a plaid print," Duprie adds. (In this case, it's the skinny bands' taupe, but in a rich plaid, you might spot some unexpected yellow or blue.) "Enhance them through your outerwear and accessories."

Old Navy Windowpane Plaid Trapeze Top, $24.94, oldnavy.com; Old Navy Mid-Rise Harper Suit Pants in Navy Plaid, $32, oldnavy.com