The moment that Andy Sachs struts into the Runway office in her thigh-grazing Chanel boots in The Devil Wears Prada is also exactly when we all knew—and believed—that she had made it in the fashion world. And that magical scene has become emblematic of all the wonderful and aspirational possibilities in life when you slip into a pair of over-the-knee boots: the fact that—if worn incorrectly— they can do just as much harm to your image as they can elevate it plays into their fantastical appeal. So to get this look right, we asked Toronto stylist Terri Dacquisto for her expert tips.


1. Find the right fit for your silhouette. “What’s great about over-the-knee boots is that they’re chic, versatile and they flatter so many silhouettes,” says Dacquisto. For petite women, try a boot with a heel—either wedge to a low-heel stiletto—that best suits your overall look and lifestyle. “Avoid slouchy styles and stick to boots that are more narrow and streamlined. And when pairing your boot and pant, stick to the same colour tone to avoid shortening the leg.”

2. Stay within the same colour palette. “Any body type can pull off this look,” says Daquisto. “The key is to remember to stay clear of too many colours when matching your pant and boot. Stick to the same colour hues to elongate your legs and body.”

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3. Make this part of your day look. To make this look work for the office, go for low heel that’s wider in thickness. “Avoid wearing a bare leg and always opt for tights or a sheer nylon,” says Dacquisto. Try pairing with a skinny trouser, button-down blouse and a fitted blazer, or a high-waisted pencil skirt with a fitted crew neck sweater, Dacquisto suggests. When heading from the office to post-work cocktails, pair a shift dress with tights and a tailored blazer for the day. “Then remove the tights and blazer, grab your favourite clutch and you’re ready for a night on the town!”

4. …and night. “Opt for a higher heel to really elongate your legs and go nylon free. Just make sure that there is some breathing room between your dress and boot to keep a long silhouette,” says Dacquisto. And keep it classy—not Pretty Woman—by avoiding plastic-looking fabrics and a body-con, too-short dress with your boots.


5. Or keep is casual. “For weekend occasions, embrace an oversized knit dress that hits mid-thigh with a flat or low heel boot,” says Dacquisto. “And for your day-to-day, grab your favourite skinnies with a long sweater or blouse and your favorite cropped coat for a winning street style ensemble.”

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