The over-the-knee boot may be one of the most difficult footwear types to wear considering its streetwalker-like undertones. But with some smart styling, the boots can elongate legs, provide some warmth, and add some extra oomph to a winter outfit. The trick is to balance out the overt sexiness with something more traditionally conservative on top: A boy-cut shirt, a boxy blazer, or a double-breasted coat can counter any skanky vibes that those boots might emanate. To temper the boots even more, find a chunky silhouette in a matte color like gray suede or a buttery brown. Click through to copy the look--with a boot we found that's under $80!
Above, clockwise from left: Street style photo by Mr. Newton; Prada Leather Bag, $1,196, available at Bluefly; ASOS Floral Triangle Silk Scar,f $33.99, available at ASOS; ASOS Suede Over-The-Knee Boot $78.19, available at ASOS; Bamford Double Breasted Coat, $899.50, available at Barneys
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Photos by Mr. Newton