How To Wear Over The Knee Boots Like A Street Style Pro

Over-the-knee boots are undeniably one of Autumn/Winter’s 16’s biggest trends, but the questions remains, how do we wear them? To avoid the danger of looking less fashion and more Pretty Woman, we’re taking cues from some of fashion’s best street style connoisseurs. From Italian designer Gilda Ambrosio to creative director and stylist Ada Kokosar we recommend taking inspiration from the pros.

Gilda Ambrosio

Gilda Ambrosio Boots

Gilda teams a pair of slouchy nude leather over-the-knee boots with an oversized satin cocoon style coat, belted at the waist. Don’t have a cocoon coat? Try pairing your boots with a classic trench instead.

Diletta Bonaiuti

Diletta Bonaiuti Boots

Wanting to channel a more casual look? Make like Luisa Via Roma’s stylist Diletta Bonaiuti and wear your boots with an asymmetric knitted skirt, a crisp white tee and a bomber jacket.

Ada Kokosar

Ada Kokosar boots

Ada always manages to look effortlessly put together. Here, she’s paired a pair of camel knee-high boots with a matching utilitarian leather gilet. When it comes to the rest of her look she’s kept it simple with a black neoprene sweatshirt and a matching wrap skirt.

Caroline Issa


Tank Magazine’s fashion director Caroline Issa keeps her look classic with an oversized mensy-shirt tucked into a textured mid-length skirt. Don’t have a bag to match your thigh-highs? Channel Caroline and off-set your look with a contrasting leather clutch.

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