5 Chic Ways to Style Over-the-Knee Boots

Cindy Linard
Published at April 17 , 2025
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Over-the-knee boots have been a fashion staple for years, and for good reason. They add instant chicness, warmth, and a touch of elegance to any outfit. Whether you’re heading out for a night on the town or looking to make a bold statement, over-the-knee leather boots are a versatile piece that can be styled in countless ways.

Below, we’ll show you five chic ways to style over-the-knee boots for women, using different styles that can elevate your look with just a few simple tips.

1. Casual and Cozy with a Sweater Dress

Over the knee boots are perfect for pairing with sweater dresses, especially during cooler months. The combination of a cozy, loose-fitting sweater dress with black over the knee boots creates an effortless yet chic vibe. Opt for neutral tones like beige, grey, or cream for a minimalist look, or go for bold colors like red or navy to add some drama.

To elevate this style, consider adding a sleek belt to define your waist, and pair it with a large tote bag. This look is great for brunch dates, casual hangouts, or even a stroll through the park. For a modern touch, pair your sweater dress with the Maryana Pointed Toe Boot. The notched topline and pointy toe of this boot give it a Western-inspired kick that pairs perfectly with the soft, feminine lines of a sweater dress. Plus, its slim heel adds just the right amount of sophistication to keep the look chic yet relaxed.

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2. Edgy with a Leather Jacket and Skinny Jeans

For a more edgy, rocker-inspired look, combine your over the knee boots for women with a classic leather jacket and skinny jeans. Black over the knee boots are a perfect match for this style as they add an extra level of coolness and attitude to the outfit. Choose a fitted leather jacket for a sleek look or a more oversized one for a laid-back vibe.

When it comes to jeans, go for black or dark-wash skinny jeans to create a seamless silhouette. If you’re looking for an added pop, pair the look with a statement graphic tee or a fitted turtleneck. To add even more structure, finish the outfit with a bold handbag or a crossbody with gold hardware.

For a slightly more elevated look, try the Riggs Knee High Boot. This boot is made from smooth leather, enhancing the modern, sleek appeal of your outfit. Its equestrian-inspired design adds sophistication and balance to the edgy vibe of a leather jacket and skinny jeans, making it an ideal choice for those who want both comfort and style.

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3. Feminine and Flirty with a Mini Skirt

Over the knee leather boots can easily be styled to create a feminine, flirty look, especially when paired with a mini skirt. Whether it’s a leather mini skirt or a cute pleated one, this combination is perfect for a night out or a fashionable day event. Pair your skirt with a tucked-in blouse, knit top, or even a fitted sweater.

For a modern, luxurious twist, opt for the Auggie Pointed Toe Knee High Boot. The pointy toe and tapered heel add an elegant touch to the look, making it perfect for any occasion. The knee-high silhouette balances out the mini skirt, making it flattering and stylish. Pairing these boots with a soft, feminine blouse or even a knit crop top adds just the right amount of contrast and sophistication, making it a perfect date night outfit or a chic option for a night on the town.

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4. Monochrome Magic with a Full-Length Coat

A monochromatic look is always a winner, and there’s no better way to showcase your over the knee boots than with a full-length coat in the same color family. Whether it’s an all-black ensemble or tones of camel, beige, or grey, the monochromatic look is chic and effortlessly stylish.

Pairing black over the knee boots with a long, tailored coat creates a streamlined, elegant look. Choose a coat that hits just below the knee for a dramatic silhouette. Underneath, opt for simple basics like a fitted turtleneck and high-waisted pants, and finish off with a minimalist handbag.

To add even more elegance to this classic look, try pairing your monochrome outfit with the Maryana Pointed Toe Boot. The Western-inspired design with its pointy toe and slimmed-down heel will elevate your look and make it stand out, while still maintaining a sleek and sophisticated appearance. This is a fantastic way to take your outfit from daytime casual to a more polished evening look.

5. Boho-Chic with a Flowing Maxi Dress

Over the knee boots aren’t just for fall and winter; they can also work beautifully with a summer maxi dress for a boho-chic vibe. Choose a flowing, floral-printed maxi dress for a soft, feminine silhouette, and pair it with knee-high boots to balance the look. Opt for lighter, neutral-colored boots like tan or beige to complement the softness of the dress, or go for a bold black over the knee boot to create a more striking contrast.

For an added touch of elegance, you can accessorize with wide-brimmed hats, layered jewelry, and a fringe bag to complete the boho look. The Auggie Pointed Toe Knee High Boot is a great option here. The tapered heel and luxe leather construction bring a refined edge to the relaxed, carefree nature of the maxi dress, offering a stylish contrast that makes this pairing both unexpected and fashionable.

So, next time you're putting together an outfit, don’t hesitate to reach for your over-the-knee boots. With endless possibilities, they’ll be your go-to fashion item for any occasion.

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