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The Ultimate Guide on How to Wear Knee High Boots Outfits for Women

The Ultimate Guide on How to Wear Knee High Boots Outfits for Women

Are you looking for ways how to wear knee high boots outfits to suit your personality and style? I'm here to help!

Neutral knee high boots are one of the most versatile pieces a woman can own. In fact, they're part of my top choices for a capsule shoe wardrobe!

These types of boots for women can be dressed up or down, worn from fall to spring, and styled to suit any occasion. 

Today on, I'll teach you how to wear knee high boots like a fashion pro. I'll show you how to style them with different styles of dresses, pants, jeans, shorts, and skirts. 

You'll learn how to wear knee high boots in both casual and elegant looks. By the end of this post, you'll be able to wear knee high boots with no second thought!

Are knee high boots in style?

Although knee boots took a hiatus for a few seasons when over-the-knee boots ruled the concrete (and actual) runways, knee boots are all-in.

From straight leg to slouchy styles, you will find them easy to coordinate with various outfits, including dresses, jeans and even in an office setting with a suit.

Thankfully there are many types of knee boots that you can choose from!

Types of Knee High Boots

From up at knee level or just above or below the knee, there are many knee boots to suit any style or occasion. Some have high heels, block heels, and kitten heels and are made of various materials.

Below are some current knee high boot styles:

  • Straight Leg Knee boots
  • Tight Leg Knee Boots
  • Slouchy knee boots
  • Materials: leather, suede, reptile print, pony hair, stretch or hybrid fabrics
  • No heel, block heel, stiletto heel

Shop for Knee High Boots at:

Shop Knee Boots for Women:

Wally Tall
FARYL by Farylrobin

How to Wear Knee High Boots Outfits 

Collage of 6 women wearing different knee high boots outfits heel outfits under text reading how to wear knee boots.

1. Knee High Boots with Jeans 

Collage of 5 women different knee boots with jeans.

There are many great outfits that go with knee high boots. And one of the most popular ways to style knee high boots is with jeans.

You can wear skinny jeans, straight leg jeans, and – yes – even wide leg jeans with knee high boots! Let's see how, below:

How to wear knee high boots with skinny jeans

If you want to create a long and lean look, I recommend pairing your knee high boots with skinny jeans. Tuck your skinny jeans into your boots to style knee high boots with skinny or slim jeans. 

If the jeans are longer, ensure you cuff or tuck them into your socks so they don't bunch up – especially at the ankles. Skinny jeans will suit any style of knee boots, whether tight and elasticized, or looser styles.

A head-to-toe all black look with black belted skinny jeans, black leather knee boots, a black tee and blazer is a timeless look. Accessories can elevate it or make it look more casual.

How to wear knee high boots with straight leg jeans

If you want a more relaxed look, opt for a pair of straight leg or less “skinny” slim jeans, like mom jeans

Tuck these into your knee boots the same as you would with skinny jeans. However, avoid too-tight boots that don't leave enough room for the pant leg.

The best knee high boots with a straight leg, boxier styles look best with straight leg jeans. Put on dark straight leg jeans, black leather knee boots, and a bodysuit for a sophisticated look.  

A distressed pair of lighter jeans, western-style knee boots, and a tee will give you a more rugged vibe. 

How to wear knee high boots with wide leg jeans

Yes, you can definitely wear knee high boots with wide leg jeans if the jeans are wide enough to fall over the boots. 

I prefer a cropped jean style to better show off the boots, like the middle woman in the image above. Just make sure the jeans are loose enough and the boots slim enough so you can't see them underneath.

I recommend a softer boot, rather than a rigid one, that will poke about inside the jeans at the knees while you walk. Check out my post on all the best shoes to wear with wide leg jeans for more styling tips!

2. Knee High Boots Outfits with Dresses 

There are many options if you want to know how to wear knee-high boots with a dress. Especially during the fall/winter seasons!

You can opt for a mini dress or midi knit dress that shows some leg between the top of the boots and the dress hem. 

If it's too cold to show your legs from above the boots, you can wear your knee boot with a flowy maxi dress or a longer sweater dress. You're good to go with a smart jacket or coat and an added scarf!

Always make sure a long or three-quarter length dress is ample enough to house the boots. Otherwise, these will add unsightly bulk under your dress. Tighter knee boots are a great workaround!

How to Wear Knee High Boots with Mini Dresses

Collage of 5 women different knee boots with mini dresses.

Knee high boots can look great with all kinds of mini dresses, from short and boxy styles to bodycon minis. 

I love the look of knee boots and mini dresses that are short enough to show 3-4 inches of the leg between the hem and the top of the boot. A short dress with knee high boots can look great with or without hose or leggings.

Opt for a high shine or metallic knee high stiletto boot with a black or leather mini dress for nights out. Add a fitted jacket and sparkly clutch!

You can also wear a simple mini dress, sweatshirt, and sweater dress casually with a suede pair of block or no-heel knee boots, or a cargo, denim or trench coat.

How to Wear Knee High Boots with Midi & Maxi Dresses

Collage of 5 women different knee boots with midi dresses.

Knee high boots work great styled with a midi dress for fall, winter, or spring. From suede boots with floral dresses that cover the boots to glossy black knee boots with slinky side-slit dresses to show them off, there is no shortage of options.

Whichever dress with knee boots you choose, make sure the hem is either above or under the top of the boots. Midi dresses that touch the edge won't look bad, but it's not ideal and can sometimes look awkward. 

Collage of 5 women different knee boots with maxi dresses.

Wear your midi dress to cover the boots or leave a noticeable gap to show off some leg. Avoid wider or bulky knee boots with tight midi dresses. 

Straight leg knee boots in black or brown make for more classic outfits with longer dresses. Great for the office with a simple shift or blazer dress. Add some quirk for a night out with animal print knee boots and simple dresses.

Check out my post for more insight on all the best boots to wear with dresses!

3. Knee High Boots Outfits with Leggings

Collage of 5 women different knee boots with leggings.

Leggings are a great option if you're unsure what to wear with knee high boots. You can wear denim-looking jeggings, leather, or cotton leggings.

These can be styled with various knee boot styles and outfits to make them fit for the office or a night out.

How to Wear Knee Boots with Leggings

Straight leg knee boots look great with simple black leggings, a loose blouse and an oversized jacket. Or you can opt for Ponte legging pants and a fitted blazer cinched at the waist with a leather belt for an office look.

Slouchy black or brown suede boots are fun and have a more relaxed look with jeggings and simple black leggings. Add a staple bodysuit and an oversized cardigan and you're everyday ready!

If it's cold outside, add a floral maxi or chunky sweater dress with your knee high boots and leggings. This is a great way to cover your bum while wearing leggings if pants aren't your thing.

Of course, leather leggings with knee high boots can look super chic, especially when your legging material matches your leather boots, creating a streamlined look.

Athletic, printed, or cut-out leggings don't usually look stylish with knee boots. But if you can make them work, go for it! 

Learn more about the all the best boots to wear with leggings in my other post.

4. Knee High Boots with Skirts

Knee boots are classic boots that can look fab with almost all styles of skirts. The key is to combine the right skirt and boots to create the look you're going for!

How to Wear Knee High Boots with Mini Skirts

Collage of 5 women different knee boots with mini skirts.

No matter the style, mini skirts will look great with knee high boots. A tighter mini skirt will suit both tight and wider leg knee boots. 

I love flared or circle skirts with more rugged boots for casual looks, but a skin-tight boot can also look great for more formal occasions.   

Tights and leggings can work depending on the look you're going for. Sparkly tights can add glam to a night out with matching opaque leggings for a streamlined look.

You can also wear knee boots during warmer months. Keep your skirt shorter and breathable and your knee high boots a lighter material such as thin leather or canvas.

How to Wear Knee Boots with Maxi & Midi Skirts

Collage of 5 women different knee boots with midi skirts.

Midi skirts offer the most versatility with knee high boots. You can wear them with a full or flared midi skirt that reaches below the top of the boots. 

Alternatively, you can wear your knee boots with a shorter midi that leaves a gap between the boots and the skirt hem. 

Pencil skirts with a side or front slit can also look great with knee boots, as long as there is enough room for the boots!

Maxi skirts look great with all kinds of knee boots. Just avoid very tight-knit skirts, where knee boots will show beneath.

Learn more about pairing boots and shoes with skirts in my dedicated post!

5. Knee High Boots Outfits with Shorts

Collage of 5 women different knee boots with shorts.

In the last couple of seasons, high-end retailers have been styling knee high boots with shorts and long coats, and I'm kinda loving it.

This look is not for everyone, but if you're looking to experiment with knee high boots to extend the wear of your shorts beyond the warmer seasons, it's a fun option!

How to wear over-the-knee boots with shorts

In the fall or spring, opt for a wide or straight leg knee high boot with high waisted belted shorts and a cozy coat. Add a pair of tights for chillier days.

You can elevate black knee high boots with an all-black look with shorts, a top and a dark grey coat for a slight contrast. Add a silky blouse if you want to add some sheen!

Add a pair of western or similarly rugged boots with a block or flat for casual, seasonally transitional looks. It'll give off a rustic vibe with a pair of denim or cargo shorts, a simple tee, or a sweater. 

How to Wear Knee High Boots FAQs

Collage of 3 women wearing different knee high boot outfits over patterned background.

Q – How to wear black knee high boots?

A – Black knee boots look good with most outfits, especially elasticized or straight leg styles. Slouchy knee boots give a more relaxed vibe that I like combining with sweater dresses, slim jeans, paperbag waist skirts and flouncy dresses. 

In terms of outfit colors, black knee high boots will go with many. You can opt for an all-black look, ensuring that the black shades are similar, so no black item sticks out.

Alternatively, you can opt for a brown, beige or all-white look to contrast your black knee boots. Denim will also look fab with black boots! Black leather knee boots are a great option to dress up your outfit.

Q – How to wear brown knee high boots?

A – You can wear knee boots with many outfits. Remember that these will make your outfit slightly more casual, especially when wearing caramel or tan knee boots.

You can keep your outfit in tone with the brown boots, by wearing lighter or darker shades of brown, tan, beige or taupe. All white outfits will also look fabulous, like a white blouse and skinny white jeans.

Slouchy brown knee boots exude a laid-back vibe with skirts and dresses. These look great paired with flared skirts and billowy floral midi dresses.

A brown boot in a lighter material or perforated style can also work during warmer seasons.

Q – Do you wear knee high boots with socks?

A – Yes, I would most definitely wear socks here. But what socks to wear with knee high boots, you ask? I like to wear crew socks with my knee boots, because they stay put, add comfort and keep my feet dry. 

Ensure that they're tight-fitting on the ankle and foot so they don't slide down while you walk.

Must make sure to wear dark socks with darker boots. If your boots get wet, the boot dyes might stain your socks.

For a boho or country-gal aesthetic, you can wear slouchy knit over the knee socks with your knee boots, so that they peak out.

Or, reach for tight thigh high socks that peek out over black knee boots. This will make it look like you're wearing taller boots instead!

Q – Can you wear knee high boots with tights?

A- Absolutely! Opaque or shimmery tights can add a festive touch to knee high boots, skirts, dresses, or shorts. 

While opaque tights can create a streamlined look, or make your knee boots outfit more conservative for a workplace or service. I will wear thick leggings or tights with my knee high boots when I want to keep warm on colder days!

Final Thoughts on How to Wear Knee High Boots

Knee high boots are one of the most versatile pieces in a woman's wardrobe. They can be elevated or dressed down to suit almost any occasion. 

I hope you're learned how to wear knee boots whether you want a casual, elegant or corporate look. All in line with today's trends and classic styling principles. 

What to wear with knee high boots is subjective, as are all styling choices! My advice is how I would dress myself or others personally.

However, if another combination of knee high boots outfits works better for you, more power to you! 

Now it's time for you to put your new knowledge into action! Go forth and conquer in your stylish new knee high boots!

Shop knee high boots from my favorites over at:

Saks Fifth Avenue
Free People 

xo ShoeTease

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