Grab the Ultimate Basic Capsule for Excellent Style All Season (For FREE)

Thanks! Keep an eye on your inbox for updates.

Best Knee High Boots To Wear With Legging To Look Chic


While knee high boots radiate style with countless outfits, there’s nothing quite like pairing them with leggings.

This duo creates a comfortable and chic look that is suitable for both daytime and evening looks.

Here, you’ll discover the best knee high boots for leggings to elevate your wardrobe no matter the occasion.

Table of Contents

Why Tall Boots Look Chic with Leggings?

Bringing these two wardrobe staples together creates an aesthetic that is not only chic, but also versatile and flattering. 

It’s a combo that marries comfort and style without sacrificing the effortless fashionista vibe. Below is a breakdown of why this pairing works so well. 

  • Visually appealing contrast. Knee-highs provide enough coverage to create a visually appealing transition from your leggings to your shoes. They draw the eye towards the legs and allow you to play up the bottom half of your outfit through contrasting textures.
  • Simple and streamlined. This duo takes the guesswork out of looking chic. It’s a style that speaks for itself through a simple and sleek silhouette. With it, you can streamline your aesthetic by making this pairing the main attraction.
  • Maximizes chic comfort. Leggings are known for their chic comfort–and the right boot can amplify their appeal. Knee-highs not only pair well with these pants, but they also effortlessly elevate your outfit.

Can you wear thigh high boots with leggings?

While thigh high boots became really popular boots choice for many, they are no longer in style. Moreover, they don’t even look that good. There is no structure to them. Thigh high boots literally look like socks. 

And if we want to elevate our leggings outfit these unstructured style of boots will not do it. So if you want to look classy, try and avoid thigh high boots.  Check out some other boots you can wear with leggings.

How To Pick The Right Style of Knee High Boots for Leggings?

If you want to elevate your leggings outfit with tall boots, here are tips to help you pick the right style of tall boots for your leggings outfit:

  • Sturdy Tall Boots: Avoid slouchy boots even though they look trendy. These boots will make your leggings outfit appear sloppy.
  • Contrast colored boots: An easy way to make your leggings outfit look chic is by adding a contrasting colored tall boots. My favorite is picking black or brown knee high boots with black leggings. It makes the outfit sophisticated.
  • Pointed toe tall boots: It does not matter whether your legs are skinny, pointed toe or square toe boots look modern compared to round toe. 
  • Block Heel Tall Boots: Instead of flat boots pick tall boots that have block heels. This will also make your legs look a bit thick if you have skinny ones. And the heel elongates and makes your outfit sophisticated.

Our Top Picks

Best Knee High Boots for Leggings

Regardless of which style of leggings you prefer, you’ll still need to find the perfect pair of boots to complete the look. 

Let’s face it–shoes can make or break an outfit. That’s why we’ve curated the best knee high boots for leggings here as a cheat sheet for a chic aesthetic.

Read on to learn more and discover your new favorite boots.

JCrew Sadie Knee High Boots

JCrew Sadie Knee High Boots in rich oak leather include a 3-inch stacked heel with a leather upper body and synthetic sole. With a shaft that’s over 15 inches, you get plenty of coverage in a roomy, soft leather style.

True to size, this boot is available in sizes 5 to 12 with a medium width. Solid neutrals will work best here when choosing a pair of leggings–such as black, grey, or beige.

These boots will be perfect for all your black leggings outfit. And if you have wide calves, these will be comfortable too.

Sam Edelman Sylvia Wide Calf Knee High Boots

The Sam Edelman wide calf knee high boots can enhance the mystique of any wardrobe. 

The almost pointed toe looks chic and modern and the slim block heels are actually comfortable to walk in.

This boot has a 2.8-inch heel, zipper closure, a 15.7-inch shaft and a 15.7-inch calf circumference (on a size 6). Keep in mind, the shaft and calf circumference increase with each size.

Sizes range from a 6 to a 12 with a medium width. For all you black boots lover, these one also come in black leather and black suede.

JCrew Stevie Knee High Boots

Looking to dress up your leggings outfit? The JCrew Stevie Knee High Boots would elevate and dress up your casual leggings outfit. Just wear a nice long sweater and coat to complete the look.

These gems feature a 1.97-inch contoured heel, soft suede and leather lining. 

For a stimulating contrast, opt for faux leather or patterned leggings. Alternatively, these shoes can be worn with solid-colored leggings for a more subdued look.

Choose from a 5 to a 12 in a medium width. Since this boot is true to size, you can order your usual.

Tory Burch Knee High Boots

The textured leather of the Tory Burch Knee High Boots makes them look luxe and sophisticated. I also love that unlike other designers, they have kept the logo detailing to minimum. This makes them versatile and you can wear them to work and other places as well.

For a size 7, the calf circumference measures 14.7 inches, while the shaft height stands at 16.1 inches. Note that every size increases these measurements by 0.39 inches.

These boots are available in both black and ginger shortbread. They are ideal for faux leather leggings or mesh cutouts. 

Sizes range from 5 to 12.

Marc Fisher Knee High Boots

Looking for a casual everyday knee high boots that you can wear with leggings? Marc Fisher knee high boots are perfect. With only 2.17 inch heel height, they are comfortable to walk in. And with wide calf easy to slide in and out as well.

Featuring a stylish almond toe box and mid-block heel, this shoe pairs well with just about any leggings style you can think of due to its neutral yet sleek design. To complete an edgier look, go for faux leather leggings.

These boots are available in sizes 5 to 12.

Vince Knee High Boots

Vince Knee High Boots will instantly make your leggings outfit looks luxe. These textured white leather look expensive and classy. 

Equipped with a 3.87-inch stacked heel, suede or leather upper body, leather lining, interior zipper and elegant pointed-toe design, these shoes will add a touch of class to any outfit.

Pick from four styles: dark amber, black, macadamia, or black-heeled.

Opt for solid or printed leggings to bring out their texture.

The size range includes 5 to 11 and is true to size.

Calvin Klein Knee High Boots

Give your outfit a contemporary upgrade by dressing it up with Calvin Klein’s Arista block heel square-toe dress boots. 

Choose between dark natural leather or black leather. This boot comes with 2.83-inch block heels, a 14.57-inch shaft height, a calf circumference of 14.17 inches and a zipper closure.

Don them with mesh cutouts, solids, or patterned leggings.

Sizes range from 5 to 11 in a medium width.

Tony Bianca Fantasy Knee High Boots

The Tony Bianca Fantasy Knee High Boots will dress up your black leggings outfit for winter. The 3 inch heel and pointed toe style looks modern and sophisticated. I love that there is not much detail in the boots which makes it minimal and expensive. But the subtle cut stitch detail makes them look interesting.

You can easily wear them with black legging even if they are black themselves because if the stitch detail. Wear them to date nights or winter clubbing outfits with leggings. 

The come in sizes 5 to 10.

Breton Knee High Boots

Subtle yet trendsetting, these Breton knee high boots will give you all the unique detailing you’ll need for a fashion-forward fit. 

Crafted from genuine black leather, these gems include black elastic gussets, futuristic gold hardware, a heel height of 3.3 inches and a 13.3-inch shaft height.

Wear them with faux leather or mesh cutouts for a sexy, elevated look.

Sizes available range from 7 AU to 10 AU.

Aerosoles Knee High Boots

Achieving a polished and contemporary outfit is easy with a pair of sleek Micah boots by Aerosoles. Available in either taupe or navy, these shoes exude modern sophistication. 

What’s more, these shoes are made by a brand that makes comfort and style a priority with every design.

Features include a 2.75-inch heel, a 16-inch shaft height, a stretchy polyurethane upper body and a zipper closure. 

Don these with faux leather, solids, or mesh cutout leggings.

Sizes range from a 5 to a 12.

Kenneth Kole Knee High Boots

Look effortlessly stylish with a pair of Lowell knee high boots by Kenneth Cole New York. These minimalist gems can be found in three designs: black leather, chocolate, or Rio red leather.

Their details include a cushioned footbed, a 3 ¼-inch demi block heel, an almond toe box, a 14 ¾-inch shaft and a 14 ½-inch calf circumference. 

Savor them with solid or mesh cutout leggings for an elevated look.

Since they are true to size, you can snag your usual. Sizes range from 5 to 11 with a medium width.


Liked This Post! Share it to support us. Thank you for Reading!


About Suchi

A Techie turned Fashion blogger, I have been in your shoes. I have gone from looking like I was trying to fit into my teen clothes, to now a stylist and blogger known to be classy and elevated style. I can help you look your best without spending too much time, effort and money into your wardrobe. 

Its all about making the right choices. Don’t forget to subscribe, so you never miss any new style guides and fashion finds. 

Want to know more? 

About The Author

Join The Club

Don't miss any posts, plus grab this free wardrobe basics checklist to upgrade your style for all seasons. 

Share Your Thoughts

What did you think about this post? Share your thoughts below.

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Join The Club

Don't miss any posts, plus grab this free wardrobe basics checklist to upgrade your style for all seasons. 

Trending Now

Where to Shop for Clothes in Your 30s Without Breaking your Wallet
Best Shops To Buy As A Grown Women For Better Style On Budget
How To Wear Belts - A Closet Essential For Women
How To Pick & Style Belts With All Your Outfits
How to Wear Blazers with Jeans
How to Wear Blazers with Jeans: 24 Ways to Look Sharp In Them
What To Wear In Your 30s to Elevate Your Style
What To Wear In Your 30s to Elevate Your Style
How to Wear High Waisted Jeans with a Tummy
9 Ways to Wear High Waisted Jeans Even with a Belly
Levis Ribcage Straight Leg Jeans Review - Why I am so Obsessed
Levis Ribcage Straight Leg Jeans Review And Shopping Guide
Want to
Dress Better?
Grab this ultimate basic capsule plan to have great style all seasons!
100+ Outfits Look book To Style Them
-----------------------------------------------------------------------Thank you for subscribing, don't forget to check your mailbox for a note from ME!