How to Style Knee High Boots: 10 Chic Outfit Ideas

how to style knee high boots

If there’s one closet staple that I find myself reaching for frequently during the cooler months, it’s knee high boots. While I feel like they kind of dropped out of trend for a brief period of time, it’s safe to say that they’re fully back in style, and honestly, I’ve been digging it.

Knee high boots look effortlessly chic, whether you’re going on a date night, heading to your office, or meeting friends for coffee. They’re universally flattering and work for various styles, which make them really fun to wear with different pieces.

I also think they’re really practical to wear because they’re comfortable and they offer your legs some extra warmth throughout the winter. Plus, they can easily be dressed up or down depending on the occasion.

Since tall boots go with so many different outfits, you might feel overwhelmed by all of your styling options. The knee high boots outfits I’m sharing below will help you figure out exactly how to wear the trendy shoes. Consider this your complete guide on how to style knee high boots!

Knee High Boots Outfits

One major perk to knee high boots is that they come in so many different styles: heeled options, flat options, snakeskin prints, leather….the list goes on. This creates the perfect opportunity to style them in your own way. It also means you can have several pairs that all have their own vibe (a girl can never have too many shoes, right?)

In the outfit roundup below, you’ll find inspiration for styling various pairs of knee high boots. Regardless of your shoe preferences, there’s sure to be an outfit that you’ll love to add to your rotation.

How to Style Knee High Boots

Knee High Boots + Mini Skirt

Styling a mini skirt with a pair of knee high boots (or even over-the-knee boots) creates the ultimate flirty and feminine combo. This outfit has such a sexy feel, and in my opinion, shows off the perfect amount of skin. I’d consider this the ideal “uniform” to wear throughout the fall and spring, when the weather is transitional and it’s not quite hot but also not cold.

Mini skirts are such a good go-to piece to have in your closet since they can be styled with so many different things (like heels, sandals, loafers.)

I love this mini skirt and would pair it a plain white shirt or sweater. Oh, and this houndstooth skirt would look adorable with black boots.

mini skirt with matching blazer and knee high boots
mini skirt outfit with knee high boots

Knee High Boots + Sweater Dress

Is there anything comfier than a sweater dress? The stretchy fabric makes for the coziest outfit, and when paired with knee high boots, you’ll be set for anything the day might bring.

A bonus is that you could wear this look year-round, since you could easily add tights when the weather is unfavorable.

Also, don’t sleep on accessories! They make an outfit feel so much more “styled” and are a great way to dress things up. Consider adding a wide brim hat, gold jewelry (I’ve been wearing these earrings on repeat), or fun purse.

sweater dress outfit with knee high boots

Knee High Boots + Shirt Dress + Sweater

There’s no denying that the preppy look is very much *in* right now, and this outfit totally highlights on that. Plus, if you’re into the Sofia Richie style, this look will help you effortlessly replicate that. It scores bonus points for being easy to throw on and comfortable to wear throughout the day.

If you’re going out to a nice restaurant or a more formal event, I’d recommend swapping out flat boots for something with a heel—a snakeskin print would look really chic!

shirtdress with knee high boots

Knee High Boots + Jeans + Coat

Of course jeans and knee high boots make a stylish combo—and it’s such a good look to have in your back pocket. Whether you aren’t sure what to wear or you just like to keep your outfits simple, this is a fool-proof choice.

Add a wool coat, scarf, hat, and some sunglasses (or just one of those accessories) and the end result will look effortlessly cool.

jeans with a coat and knee high boots

Knee High Boots + Jeans + White Button-Up

This outfit proves that skinny jean aren’t out of style. Knee high boots are soooo much easier to wear with tight jeans since they don’t cause them to bunch up. You could also try a straight leg pair if that’s all you have on hand but I’d avoid anything that has a wide fit.

For an everyday look that’s practical yet feels high-end, style a white button-up shirt with your go-to denim. I love white button-ups because they can be worn with so many different outfits and during all seasons.

This outfit would also look cute with a pair of ankle boots. If you need some ideas on how to wear ankle boots, I’ve got lots of ideas here.

jeans and a white button up shirt with knee high boots

Knee High Boots + Black Jeans + Blazer

Need an outfit idea that’s appropriate for the office? This is it.

A blazer is a classic piece that offers a professional, polished vibe. Pair one with your favorite black jeans and knee high boots and you’ll have an outfit that’s ideal for meetings, networking events, or a post-work happy hour.

If you want to give this look a more girly feel, just add a belt. It’s a simple way to make it more of your own.

black jeans and black blazer with knee high boots

Tip: If you want to switch things up, consider adding a pair of riding boots to your shoe collection. They have an elevated and timeless feel, and they’d look cute with all of these outfits.

Knee High Boots + Leather Leggings

Just like knee high boots are a go-to staple for me during the winter, so are leather leggings. I always have these stretchy, cozy pants on rotation throughout the fall, winter, and even into the spring.

They’re a great base layer to throw on regardless of where you’re going or what your day entails. They also match with so many pieces, like sweaters, t-shirts, blouses, etc. My go-to move is to slip a trench coat on as the final touch (I love this Amazon find.)

In both of the photos below, I’m wearing my Stuart Weitzman black boots (which I am truly obsessed with) but you could wear any black pair that you like.

Knee High Boots + Mini Dress

Another outfit idea that has a majorly flirty vibe? A mini dress with some knee high boots. I love that this look only requires two pieces and then you’re out the door. So easy yet so chic.

I’ve been very into wrap style dresses lately, but any dress you like would do! Also, you could branch out and go with a midi dress if that’s more your thing.

Knee High Boots + Leather Jacket

To achieve the ultimate cool girl vibe, try styling your knee high boots with a mini skirt or dress and a leather jacket.

I swear that a leather jacket does so much good in a wardrobe—it’s another piece that can work well with a lot of things and throughout many seasons.

If you want to keep things casual, I’d suggest going with a plain t-shirt dress and then dressing things up with your boots and jacket. This will let those two pieces be the stars of the show.

Knee High Boots + White Jeans

Don’t sleep on white jeans! You don’t necessarily see a ton of people wearing them these days, but they’re such a classic pant option and they offer a way to break up your everyday denim look.

I paired my white jeans with a beige sweater (I love styling brown and white together) and then added some suede over-the-knee boots, but any boots would do.

What’s your favorite way to style knee high boots? Let me know in the comment section below!

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