Styling Over-the-Knee Boots

Styling Over-the-Knee Boots

Of all the essential wardrobe staples fall is known for, boots are undoubtedly at the top of our must-have list for the autumn and winter months. While specific boot trends come and go, there’s one in particular that has been a favorite for the past few seasons: the over-the-knee boot. Though admittedly a bit intimidating at first, the popular style is surprisingly versatile and easy to incorporate into your everyday wardrobe. In fact, when worn in just the right way, the thigh-high boot can instantly transform an ensemble, taking it from average to statement-making. For inspiration, follow these easy tips for styling over-the-knee boots in three different ways.

With a Mini Dress
Wait, You Need This
Wait, You Need This

When the temps begin to dip, a mini dress is likely the last thing you would think of wearing. But, when paired with over-the-knee boots, super-short hemlines become season-appropriate (not to mention sophisticated and sexy). After all, pulling off over-the-knee boots is all about creating a perfectly proportioned look—something the mini dress and thigh-high boot, when combined, absolutely nail. Choose a mini dress whose hem falls an inch or two above the top of your boot for just a sliver of skin. Then, add a pair of tights for extra warmth (if needed), top with a coat, and you have an ensemble that absolutely reads casual off-duty cool.


Sweater: Zara | Denim Overall Jumper: H&M | Boots: Zara | Fur Clutch: Cache

For an alternative to the mini dress, give a denim overall dress a try. The 90s-inspired staple is not only back in full force for the fall season, it’s as comfortable as your favorite pair of jeans and just as versatile, too. Wear the same way as you would a mini dress with a chunky knit underneath, and you’ll be cozy and comfy all season long.

With Jeans
Simply Cyn Over the Knee Boots
Simply Cyn

Jeans are a wardrobe necessity in any season, but they become the easy go-to we reach for again and again during colder weather. Thankfully, boots and jeans were made for each other, including (or maybe even especially) the thigh-high boot. For a simple outfit formula that’s equal parts chic and casual, pair dark-rinse skinny jeans with an over-the-knee boot. The shape-skimming cut of skinnies are the perfect match for the equally form-fitting thigh-high boots. Opt for a heeled style that hits an inch or so above the knee to lengthen legs and create a lean silhouette, and offset the style with a biker jacket to strike the ideal balance between the top and bottom portions of your outfit.

With a Pencil Skirt

Though the over-the-knee boot can certainly seem a little too va-va-voom for the office, it can easily become a key part of your weekday wardrobe—when paired with the right pieces. To make the thigh-high style work-appropriate, opt for a pencil skirt that hits below the knee or an A-line midi skirt that isn’t too restrictive over the shafts of your boots. The layering effect of a longer skirt over thigh-high boots is chic yet reserved, minimizing the amount of skin that’s showing and creating a polished look that works for the office or off-the-clock occasions.

How do you style over-the-knee boots?

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  1. Love the suggestion for over the knee boots but I have problems because my legs are on the chunky size. Being a big bone person can make this a task. I’m losing so by winter I’ve this problem solved. ????

    1. You should look for boots that tie in the back, because those allow for some flexibility in adjusting for healthy thighs! I’ve also seen stores like Ashley Stewart carrying OTK boots