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Fall is finally here, and we’re ready to get cozy with the changing leaves, pumpkin-flavored everything, and, of course, our best over-the-knee boots. We all know it’s challenging to dress for the cold weather when seemingly countless options are available online. As we head into the cooler months, your wardrobe may transition from a summer-inspired look to a more fall/winter vibe. However overwhelming it may seem, shoes are a simple yet effective way to switch up your fall outfits without having to buy an entirely new wardrobe.

This year, over-the-knee boots are back in the spotlight and demanding some floor space in your closet.

Falling Boots Solved with this Pro Tip

Our biggest concern with thigh-high boots is a phenomenon most women have experienced. Let’s set the scene: it’s a Friday night, and you’re rocking a fresh blowout and your most reliable pair of dark-wash denim. You slip on a crisp white button-down with a strategic French tuck, and you’re almost ready to go. This outfit might remind you of Business Casual Fridays, and maybe that wasn’t exactly your objective. So, you turn up the heat on this look with a pair of black over-the-knee boots, a voluminous high ponytail, and gold accent jewelry, and head out the front door to enjoy your night.

As you walk to your car, you already notice the dreaded feeling of bunched-up material behind your knee. Cue an instant eye-roll. We have totally been there and know how you’re feeling. Nothing puts a damper on a night out like having to lean over to readjust your thigh-highs every couple of minutes. Give yourself one less thing to worry about by selecting boots that will stay right where they’re supposed to. Or… pro tip alert! Use double-sided fashion tape, like this Fearless Body & Clothing Tape from Amazon, to adhere the inside of your boots to your skin or whatever material you’re wearing. We like this one, mainly because it’s fabric-friendly and won’t irritate your skin!

Finding the Best Over-the-Knee Boots

If you’re looking for something that can take your casual outfits up a notch and add some spice to what you already have in your closet, consider investing in the best over-the-knee boots. These stylish shoes are versatile enough to fit with any type of outfit – from business to playtime.

To help you find the perfect boots for fall, we’ve put together a list of our all-time favorite thigh-high styles. Our team has chosen these timeless pieces because they keep you prepared for whatever weather forecast you may have while looking great with anything, from jeans to dresses and skirts.

Scroll down for our top recommendations!

High Heeled Styles

1. Kelsi Dagger Brooklyn “Logan Over the Knee Boot” from Nordstrom

Starting our list off strong with these highly rated suede Kelsi Dagger Brooklyn boots. At this $225.00 price point, choose the round toe, 15” calf circumference, and 3.5” chunky heel style in one of five different color options—Chestnut, Coffee Bean, Warm Gray Suede, Espresso Snake Skin, and Olive Suede. The customer reviews on this pair honestly had us sold! Many women suggested rolling the boot down to your ankle before pulling it up to ensure the snuggest fit and most comfortable tucked-in pants.

2. Jessica Simpson Louxie Over the Knee Boot from DSW

These skintight OTK boots by Jessica Simpson are to die for! You can’t go wrong with the form-fitting material, 4” covered heel, and 14 ¾” calf circumference. The Black and White Snake Print is guaranteed to make a bold statement this season, but these beauties are also available in plain black. Check out the product reviews on the DSW website for plenty of outfit inspiration from past buyers.

3. Steve Madden Vava Cognac Patent

Steve Madden brought the sex appeal with these Vava Cognac Patent Boots! This skin-tight leather with a pointed toe and stiletto heel will definitely have you turning heads all season long. If you want to add more color to your shoe collection, try out one of this style’s eight colors—from bright red to vibrant yellow, even camo print!

Cute and Comfy Flats

4. Vince Camuto Women’s Hailie Fashion Boot from Amazon

Every woman should have a classic pair of black thigh highs in her closet—and this pair is a great contender! The flat heel and accessible zipper detail make these beauties great for everyday use. We love the almond-shaped toe and comfortable stretch material, too! Pick from one of four color options to amp up your fall fits.

5. Steve Madden Bronte Black

Channel your inner rock star with these fashion-forward thigh highs! Skin-tight with just the right amount of detail. Throw on your best leather outerwear, or keep it casual with a denim jacket—the styling options are endless.

Wide Calf Selection

We have to say; we did a little deep diving to find the best boots for our gals with muscular calves. One of the biggest struggles when it comes to riding boots in the fall is making sure that they actually fit your legs comfortably. So, if you’ve been having a hard time finding the perfect pair for you, we feel your pain! After some research, here is our “wide-calf” selection:

best over the knee boots

6. Black Faux Suede Over the Knee Boot (Wide Width & Wide Calf from Torrid

We’re giving Torrid a round of applause for this pair of two-toned boots, which are “designed so you never have to size up again!” There’s even a breakdown of calf circumference by size available in the product description. Torrid has a fantastic shoe selection especially made for women with wider calves. On-trend style and guaranteed comfort? We’ll take them!

7. Journee Collection Women’s Wide Calf Kaison Boot from Macy’s

Check out this pair of over-the-knee boots from Macy’s with a rounded toe, high shaft height, and comfortable block heel that will fit comfortably on wider calves. We love this pair for its five different color options, like Black, Gray, Stone, Taupe, and Wine. Wine is the perfect pop of color to add to your neutral outfits this fall!

Conclusion

One thing we love most about fall is the opportunity to rock gorgeous boots. Whether you want to dress for a day out on the town or an evening event, over-the-knee boots always make our list as one of the top footwear trends this season.

We can certainly make your search a little easier to find the best over-the-knee boots. We’ve rounded up some of our favorite styles from brands like Steve Madden, Vince Camuto, and more so you can stay ahead in style without breaking your budget. These are our favorite picks for OTKs that prevent blisters from forming on your feet and won’t slide down while you walk! So go ahead and order one or two pairs today – it’s never too late to invest in an outfit piece that is worth every penny. Which ones will you be adding to your closet?

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