How to Style Those Over-the-Knee Boots

Some trends are so incredibly audacious that attempting them is an exercise in valor. Amidst a sea of plunging necklines, mini skirts, and bold prints, how to wear knee high boots is a stylish query that somehow trumps all others in its difficulty of mastery. To blame Julia Roberts' iconic thigh high boot in Pretty Woman seems unmerited; after all, thigh highs had a raunchy reputation all their own before Roberts paired them with a neon bodysuit and mussed curls for her role as a lady of the night.

However, the past several years have seen an upswing in the popularity of over the knee boots regardless of their lascivious connotations. Ariana Grande sported a pair so high they nearly consumed her diminutive frame at the 2014 MTV Video Music Awards; Rihanna seems to possess a growing collection which she pairs with everything from slouchy sweaters to bodysuits; and the Kardashian clan appears to believe that wearing thigh highs makes sporting other clothing unnecessary. A daunting as the statement may seem, thigh high boots can elevate a basic wardrobe and infuse modernity into classic pieces. The key to riding the line between stunning and striptease-appropriate is the items you pair with your pair. For the uninitiated, read on to discover how to wear over the knee boots in a modern fashion.

1. Pair With Plaid

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Unless worn in the irreverent, punk-ish manner of Vivienne Westwood, plaid is a fabric that smacks of tradition and polish. Therefore, pairing plaid with cheeky footwear like thigh high boots like editor Miroslava Duma creates a dynamic overall effect which perfectly balances edge with elegance.

2. Add An LBD

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If the notion of wearing your preferred LBD with your basic black heels to yet another social engagement makes you want to sigh with sartorial boredom, pair that frock with your over-the-knee boots instead. Thigh highs add an instant rakish angle to the closet staple, and will keep your legs infinitely cozier than stockings and heels.

3. Wear With Business Casual

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What better way to lend sophistication to a pair of sultry over-the-knee kicks than by sporting them with professional attire? A charcoal blazer, pussybow blouse, and pencil skirt contrast with the playful aspect of thigh highs for an authoritative yet outré effect.

4. Slip On Over Jeans

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Over-the-knee boots need not be your go-to shoe for a mini skirt or sweater dress; in fact, the style is ideal for formalizing a pair of skinny jeans. Wear your pair with denim in a matching hue for a more streamlined look, or color block them with contrasting jeans for a less buttoned-up appearance.

5. Match With Coordinating Tights

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If the notion of wearing high-heeled thigh highs is a bit too ostentatious for your taste, try pairing your boots with matching, opaque tights. You'll still gain height and a leg-lengthening effect from the look, but your boots will blend into the line of your stockings for a more seamless, demure appearance.

6. Incorporate Tweed

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Tweed is the universally acknowledged fabric of Ladies Who Lunch, making it the ideal candidate for pairing with thigh high boots. A sharp tweed blazer and thigh highs announce to the world that you mean business, but you also possess dash of creative flair.

7. Suit Them Up

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Sometimes, a suit needs innovative accents to keep it from tedious territory, and thigh high boots are just the accessory for the job. Keep the palette of your ensemble black and what for a more dramatic, urbane appearance.

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