Over-the-knee boots can feel intimidating. Trust me, I get it. For years, I watched other women wear them from afar, thinking they were “too much” for me. Especially since I had curves. Listen, I discovered that I (and you) can rock over-the-knee boots! And, that we should since they’re a wardrobe staple that can transform boring winter style into something fun while keeping you warm. This is one of my most popular posts!
This post was originally published in January 2022 and updated January 2026. Links have been updated for sold out items.
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This is one of my most popular posts! Here are the two ways I wore these boots when I first created this post back in January 2022. I got some other ways to wear these boots. Keep scrolling to hear about the other two outfits.
Look 1: Cardigan and Jeans
First, let’s start with the outfit that surprised me the most. I used to think over-the-knee boots needed to be paired with dresses or skirts to work. Not true! You can totally wear OTK boots with your jeans.
The Formula: Off White Peplum Cardigan + Skinny Jeans + Camel Over-The-knee Boots
This look is the perfect example going casual while looking put together. It’s polished enough for a lunch date, but comfortable enough for running errands, or meeting friends for matcha. The key to making this work is the fit of each piece and how they work together. Also, making sure you are comfortable!
This basic cardigan but not as formal as a blazer—that perfect in-between piece. The off white color keeps everything fresh and bright, even in the middle of winter. This type of cardigan sweater is versatile and can be dressed up or down depending on what you pair it with.
My high-waisted skinny jeans are essential when wearing over-the-knee boots because they create a smooth, continuous line. You don’t want any bunching or gaping between your jeans and boots—that’s what makes the outfit look sloppy instead of sleek.
The OTK boots work so well since they have a heel (more on why that matters in a minute), and they stay up without constant adjustment. The cognac brown color is versatile—it works with virtually everything in your closet and feels less severe than black.
Shop the Look
Love the casual outfit? I’ve linked everything you need to recreate it:
- Off White Peplum Button Cardigan – size Large
- Levis Skinny Jeans (high-waisted, true to size)
- Brown Over-the-Knee Boots with heel
- Brown Leather Hobo Bag
Want to recreate the elevated look? Here’s what you need:
- Black Long-Sleeve Bodysuit– size Large
- Tan Corduroy Mini Skirt (stretchy, comfortable fit)
- Black Over-the-Knee Boots with heel
- Black Belt (to define the waist)
- Structured Purse (to finish the look)
“The over-the-knee boot trend shows zero signs of slowing down. We’ve embraced their over-the-top nature..“
Source: Harpers Bazaar
Look 2: The Mini and Boots
Next, this is the outfit that made me fall completely in love with over-the-knee boots. It’s girly with a bit of an edge. Makes you feel like you have your life together (even if you’re just figuring things out – hahaha).
The Formula: Black long-sleeve top + tan corduroy mini skirt + black over-the-knee boots
This combination is the perfect balance between polished and approachable. It’s not so dressed up that you’ll feel overdone, but it’s polished enough for date night or dinner with friends.
The black bodysuit size large, this fitted top creates a streamlined silhouette that we love! Black provides the perfect neutral base that lets the boots and skirt be the hero pieces. The long sleeves keep you warm without adding bulk.
The tan corduroy mini skirt is so good. The skirt hits at mid-thigh, showing just a bit of skin between the skirt hem and boot top. That exposed leg is what makes this outfit work—it prevents the look from feeling too heavy or overwhelming. The neutral tan color is perfect for winter and works great with both black and brown boots.
The Black Over-the-Knee Boots: These boots in black give the outfit a sleeker, more dramatic vibe than the brown pair. The heel adds height and creates a long, lean line from hip to toe. The belt at the waist cinches everything together and creates definition.
Why These Outfits Actually Work
Get a Pair with Heels: This is non-negotiable for me. Heeled over-the-knee boots have structure and shape that helps them stay up better. Plus, they avoid that “pirate boot” slouch that can happen with flat boots. The heel also gives you more styling versatility—you can wear them with everything from jeans to dresses.
Make Sure They Stay Up: The whole point of over-the-knee boots is that they stay over your knee. Look for boots with some stretch or grip at the top. Nothing ruins an outfit faster than constantly having to pull up your boots throughout the day. Both pairs I’m wearing have enough stretch to fit my legs comfortably while staying securely in place.
Show Some Skin: The small section of exposed leg? That’s intentional. Whether it’s the gap between jeans and boots or between skirt and boots, that little bit of skin prevents the outfit from looking too heavy or costume-like. It creates visual balance and keeps things modern.
Choose the Right Colors: I stayed away from black boots for the casual outfit and went with cognac brown instead. This makes the boots stand out without overwhelming the look. For the elevated outfit, black creates a sleeker, more dramatic effect. Think about the vibe you want—brown feels more relaxed and versatile, while black feels more polished and bold.
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Styling Tips for Over-the-Knee Boots
After years of wearing and styling over-the-knee boots, here are my top tips:
Proportions Matter: If you’re wearing a longer top or sweater, tuck it in or pair it with something fitted on bottom. The goal is to avoid looking like you’re drowning in fabric. Define your waist with a belt if needed.
Hem Length is Key: With skirts and dresses, aim for a hem that hits mid-thigh or slightly above the knee. Too long, and you lose that gap of skin. Too short, and you might feel uncomfortable.
Keep the Rest Simple: Over-the-knee boots are a statement piece, so let them be the star. Stick with simple tops and classic silhouettes. Save the bold prints and colors for outfits with regular boots.
Tights are Optional: For the skirt outfit, I prefer going bare-legged. It creates a cleaner, more intentional look. But if it’s super cold or you prefer coverage, nude or black tights work perfectly fine.
Try Different Colors: Don’t feel like you need to stick with black. Brown, tan, gray, and even burgundy over-the-knee boots can be incredibly versatile and give you more styling options.
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Building Your Boot Wardrobe
If you’re ready to get over-the-knee boots, here’s what to look for:
The Essential Features:
- A heel (even a modest one makes a big difference)
- Stretch material at the top to accommodate different leg sizes
- Quality construction that will last multiple seasons
- A shaft height that actually goes over your knee when you sit down
- Comfortable sole padding for all-day wear
What to Pair Them With:
- Fitted jeans or jeggings in dark washes
- Mini skirts in neutral colors
- Sweater dresses that hit at mid-thigh
- Bodysuits that stay tucked in
- Long cardigans for added warmth
The Investment Pieces Worth Having:
- One pair of brown/cognac over-the-knee boots
- One pair of black over-the-knee boots
- Quality jeans that fit your curves properly
- bodysuits or fitted tops in neutral colors
- At least one mini skirt that works for your body type
These pieces will mix and match to create dozens of outfit combinations. You don’t need a massive wardrobe—you need the right pieces that mix and match.
Final Thoughts
Over-the-knee boots aren’t as intimidating as they seem. With the right styling approach, they’re actually one of the most versatile pieces in your winter wardrobe. They keep you warm, they’re flattering, and they make even the simplest outfit look intentional and polished.
The key is finding boots that fit properly and styling them with pieces that work with your body and your lifestyle. Start with the casual outfit if you’re nervous—jeans and boots are a natural pairing that feels less intimidating. Once you’re comfortable, branch out to the elevated look with skirts or dresses.
Most importantly, have fun with them! Fashion should make you feel good, not stressed. If over-the-knee boots make you feel confident and stylish, then wear them! It is not that serious!
Stay warm, stay stylish, and remember—you can absolutely rock over-the-knee boots at any age, any size, any time. Follow me on Instagram @livbyviv for daily inspo and behind-the-scenes looks. And if you loved these versatile styling ideas, check out more style posts here.
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