What to Wear with Knee High Boots: 16 Outfits to Copy Now

Looking for cute knee high boots this season and knee high boots outfit ideas? You don’t want to miss this. This post contains affiliate links at no extra cost to you.


Winter is coming and now is the time to dust off your favorite knee-high boots. They are the perfect footwear option for the colder months as they help keep you warm but are still very stylish.

Knee-high boots can be a little tricky to style and may require a little more effort and thought but they can look so good if styled right.




Knee High boots come in an array of styles and colors. We’ve narrowed it down to 4 must-have styles that will fit seamlessly into your capsule wardrobe collection.

Here are 4 types of boots to try now:


Probably the most versatile option, black boots will allow you to wear them with multiple outfits.

They are a classic style and timeless. You could play around with the material, but a classic faux leather boot is ideal.

You could also try a suede option which elevates the footwear and can easily be dressed up.


Brown boots look stunning for winter and pair so nicely with many other fall and winter colors.

I love brown against navy, burgundy, beige, and ivory. The look is so sophisticated and softens a look, unlike a black boot.

Brown boots also look great with denim and give an outfit a more casual look.


Boots with a tall heel instantly look more chic and dressed up. Opt for heeled boots with a pointed toe to elongate your leg and make you look taller.

If you are not a fan of tall heels, you could opt for the new hot trend of kitten heels. Not only is it more comfortable to wear but still gives your leg a lift to give you the same look.


Flat boots are a great option for those who are on their feet a lot or for people who commute to work on foot.

They are a more comfortable option but can be less dressy. Many of the flat boots worn today have chunky heels and can be a little more overstated.

I do love how they look dressed down with leggings and an oversized sweater as seen below. Or look for a pair with a more streamlined and classic fit like the ones on the right.


Yes, knee-high boots are in style for the 2023/2024 winter season.

Last year, we saw a twist on the classic boot with a bit of Western flair. There were a ton of western tall boots worn during Taylor Swift’s Eras Tour.

We also saw a ton of chunky lug-sole boots in the past couple of years. If you’re not a fan, great news, they may be on the way out.

If you’re looking to get ahead of the trend for 2024, I suggest you look for either a classic black knee-high boot (if you want to play it safe.)

This year we’ll see a ton of pointed-toe and smaller heeled boots. The silhouette is sleek and streamlined with the exception of a snake-embossed boot here and there.

This style is a little more understated but will pair well with skirts and dresses for winter.

We also saw a ton of over-the-knee footwear on the runways during New York Fashion Week. More notably, slouchy and eye-catching designs.

What do you wear knee-high boots with?

When styling knee-high boots, you will want to consider the occasion you will be wearing them. For a more casual look, leggings or jeans would pair well with boots.

If you’re going to a baby shower or grabbing brunch with friends, pair knee-high boots with a mini dress that hits above the knee.

You can even wear tall boots to work. Style them with a midi skirt or maxi dress and throw on a blazer for a chic workwear outfit. I would suggest staying clear of trendy boots such as lug soles and western boots.

If you are going to wear them with jeans, be sure they are skinny jeans. This will keep your denim from bunching up and looking sloppy. Go for dark-wash jeans to elevate the look. Or opt for black jeans for a fresh look.


Yes, you can wear knee-high boots to work. To make your outfit office-appropriate, wear your knee-high boots with a midi skirt or maxi dress. Try to keep the boot more classic in black, brown, or beige.

10 Neutral Capsule Wardrobe Outfit Ideas with Knee High Boots

A neutral capsule wardrobe is a great way to create a variety of stylish outfits with minimal pieces. Here are ten outfit ideas for knee-high boots using a neutral color palette:

  1. Classic Elegance:
  • Pair your knee-high boots with black skinny jeans, a white silk blouse, and a tailored black blazer for a timeless and sophisticated look.
  1. Monochromatic Chic:
  • Combine beige knee-high boots with beige trousers and a matching turtleneck sweater for an effortlessly stylish monochromatic outfit.
  1. Casual Cool:
  • Wear your knee-high boots with distressed gray jeans, a white t-shirt, and a gray cardigan. Add a statement belt for extra flair.
  1. Cozy Layers:
  • Create a cozy fall outfit by teaming your boots with brown leggings, an oversized cream sweater, and a camel-colored wrap scarf.
  1. Effortless Minimalism:
  • Pair your boots with a black midi skirt and a simple white tee. Add a black leather jacket for an edgy touch.
  1. Business Casual:
  • Style your knee-high boots with a knee-length gray pencil skirt and a light gray blouse for a professional yet fashionable office look.
  1. Winter Warmth:
  • Combine your boots with dark gray wool pants, a white turtleneck, and a camel coat for a chic and warm winter outfit.
  1. Casual Layered Dress:
  • Wear a knee-length sweater dress with your boots and add a long cardigan and a belt to cinch at the waist for a trendy, layered look.
  1. Weekend Comfort:
  • Opt for distressed boyfriend jeans, a white button-down shirt, and an oversized beige cardigan for a laid-back weekend ensemble.
  1. City Chic:
  • Pair your knee-high boots with black leggings, a black turtleneck, and a camel trench coat for a sophisticated city look.

With these outfits, you can mix and match the basics to create a variety of stylish and neutral-toned looks while making the most of your knee-high boots. Adding a few key accessories can help change the style and adapt these outfits for various occasions.


If you’re stuck on how to wear and style your knee high boots, no worries! We’ve got you covered. Here are 8 additional knee high boots outfits to copy this season.


This post was all about knee high boots.

Hi there! So happy you're here. My name is Maria -- content creator, blogger, wife, mother of 2 and lover of all things fashion, beauty, and home. Take a look around...I think you'll like it here.

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