The perils of thigh-high boots are multifold, from up-skirt peeks to the Olympic muscle needed to slide those babies off trapped, sweaty thighs. They’re one of the most difficult pairs of shoes to wear successfully with bold confidence, along with strappy stilettos, athletic shoes with rounded heels for toning your butt, and any footwear with a Lucite platform heel.
But alas, boots were made for walking, and any self-assured lady can pull them off. Just look at Mossy. Thigh-highs serve dual functions, adding leathery sex appeal while protecting your toes from the elements. There’s a certain burlesque eroticism about having to unzip the boots from your thigh aaall the way down to your feet. Like you’re undressing secret, naughty parts of your legs.
And yet, they’re suitable for fall and winter weather, family reunions and most work occasions. Stay modest by wearing a dress or skirt that drops down past the top of the boots. The outfit turns tramp when the lowest edge of a tight skirt just barely skims the top of the boots (but you can balance with a chunky sweater or turtleneck and a low heel).
This fall, why not steer away from tried-and-true Frye riding boots and instead splurge on a pair of leather or suede thigh-high boots? Take the following cues from edgy fashion darlings 3.1 Phillip Lim, Acne and Rick Owens. Your future self will thank you for pulling such a daring move.
Top Picks:
These adorable 3.1 Phillip Lim thigh-highs from the runway collection sport a chunky heel and an angled sheath of leather that looks like an over-the-knee protector from the Hunger Games or a medieval shield. Leave it to Balmain to design classic black thigh-high stiletto boots that would be an apt substitute for black leggings. Sleek, sophisticated, minimalistic. No extra details needed. (If you’ve worn black leggings too many times already, black thigh-thighs are a great alternative.) On the weekends, break out of your usual go-to booties and slip on these midnight blue Acne beauties with gold foil color blocks on the front. Or, try these Cesare Paciotti stilettos, which pair suede and leather with a thin devilish red line separating the two fabrics. Still not sartorial enough for you? Then Rick Owens has got the perfect pair for you: skintight platform thigh-highs with a rounded almond toe. Head-turning and envious looks guaranteed.
How to Pair:
The key is remembering the hem-to-thigh ratio. Short hem plus tottering thigh-high boots with heel = tramp. Don’t be a tramp. Keep it simple with skirts that drop past mid-thigh. Or, if you’re going for megawatt attention with killer Rick Owens-like platform boots, then wear a dress slightly more modest, such as a tight, long-sleeved body-con with an open back. For 9-to-5 workdays, definitely choose longer maxi skirts cinched at your waist with a statement belt. Whatever you do, if you’re in the office, don’t show any thigh skin.
