Think fast! Plaid—preppy, polished or punk? This season, that is the question to answer. It depends on how you put your pieces together: Team Black Watch trousers with a crisp white shirt, wear tartan pumps with an LBD, or strike an unconventional note with a Prince of Wales topper over skintight pants. We suggest trying all of the above. Fashion Director Cindy Weber Cleary tells us how to pull it off. Runway inspiration: Versace; celebrity inspiration: Miranda Kerr

Why I Love This Look:
1. It’s punchy! Tartans can pack a wallop, even in small doses, such as on fierce high-heeled pumps, button-trimmed gloves or a structured, ladylike bag.

2. I gravitate toward linear patterns like stripes and plaids—symmetrical designs have a visceral appeal. Their regularity is reassuring and pleasing to the eye.

3. But I also appreciate when something so predictable goes off the rails. Recently, Uniqlo‘s newest design director, Nicola Formichetti, created head-to-toe ensembles out of plaid shirts tied every which way for the company’s fall presentation. Brilliant! Try tying a plaid shirt around the waist of a feminine dress—I used to do this in my 20s!

How to Pull It Off:
1. For heaven’s sake, don’t pair a schoolgirl kilt with a proper little navy blazer—unless you add studded black booties! You don’t want to look too preppy.

2. Many fall fashion shows—Hedi Slimane’s Saint Laurent and Donatella’s Versace, most notably—evoked the British punk scene of the ’80s. If you’ve already been there, done that in real time, don’t revisit it.

3. Instead, go the sophisticated route: Slip on a tartan jacket with a black leather pencil skirt and pointy pumps to look both elegant and provocative. Or opt for plaid cigarette pants with a tuxedo jacket and strappy sandals. Sexy shoes are definitely called for with this classic pattern.

Integrate the trend into your wardrobe—stat—starting with these 10 smart finds:

SHOP PLAID PIECES

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Britney’s InStyle Cover Look

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—Cindy Weber Cleary