How to Wear Knee High Boots

Knee high boots are currently a fashion favorite, and for good reason. They are not only trendy, but timeless. Also, they’re incredibly versatile, suitable for every season and occasion, whether you’re going for a dressy vibe or a casual look. So, today, I’m excited to merge the best of both worlds by sharing some practical yet stylish tips on how to effortlessly wear your knee high boots. From sophisticated outfits to more relaxed looks, I’ll share various styling ideas that can instantly elevate your look. Additionally, I’ll share some of my top picks for knee high boots that you’ll want to add to your collection. So, if you’re looking for more inspiration on how to get the most out of your knee high boots, stay tuned!

Also, for more chic boot styling ideas, be sure to check out my posts on How to Wear Ankle Boots, How to Style Chelsea Boots, and Western Inspired Cowboy Boots as well.

How to Wear Knee High Boots

How to Wear Knee High Boots

With a Sweater Dress or Knit Dress

Wearing knee high boots with a sweater or knit dress is a stylish choice and it is especially perfect in the colder months. This combination will not only keep your warm, but keep you feeling chic and sophisticated. Also, if you’re looking for that perfect sweater dress, there are many great options here to suit any style. If you’re like me and you love sweater dresses check out my post here for more great ideas on how to style them.

With a Skirt

Styling your knee high boots with different types of skirts is a great way to elevate your look. Pairing them with a pencil skirt offers a sleek, professional vibe, while a slip skirt adds a touch of effortless elegance. For a cozier feel, a knit skirt works perfectly to not only keep you warm, but stylish. This chic combination will take you effortlessly from the office to date night and more.

With a Lace Dress

For dressier occasions, style your knee high boots with a lace dress. It can also easily be adapted for work by layering on a blazer. This combination strikes a balance between elegance and professionalism. Don’t forget to style your accessories to match your boots to create a chic and seamless look.

With Wide Leg Jeans

Pairing your knee high boots with wide leg jeans is a fantastic way to create a look that can be dressed up or down. Whether you opt for a relaxed light wash or a sleek dark wash, wide leg jeans provide a stylish foundation for a versatile outfit, creating a look that’s perfect for various occasions. For a more dressy look, go for dark wash jeans with a black or brown boot. Then add a blazer or blouse. For a more casual look, pair your light wash jeans with a t-shirt and relaxed knee high boots.

Over Your Jeans

Wear your knee high boots over slim jeans for a classic look that never goes out of style. It’s important to choose slim fit jeans to ensure a sleek silhouette when paired with the boots. Then add a blazer if you want to elevate the classic jeans and boots combination to a chic, sophisticated outfit. If you’re a fan of this combo, be sure to check out my blazer and jeans blog post for more inspiration on how to style this look.

Over Your Leggings

Just like styling your boots over jeans, wearing them over leggings offers another chic look that’s ideal for more casual occasions, from traveling to running errands. Leggings provide a comfortable and versatile base that pairs effortlessly with knee high boots. This combination is perfect for creating a sleek, put-together look that doesn’t sacrifice comfort, making it a great choice for those on the go moments.

With a Slip Skirt or Slip Dress

Pairing your knee high boots with a slip skirt or slip dress is something I love because of the elegance and elevated look these pieces bring. You can create a sleek, monochromatic ensemble with a black slip dress and matching black boots, or mix it up with different colors for a unique twist. For more ideas on how to style slip skirts check out my dedicated post here for more inspiration.

With a black mini skirt

Pairing your knee high boots with a black mini skirt is a versatile and chic choice for any wardrobe. The combination is effortlessly stylish, suitable for various occasions. For a sophisticated workwear look, team the skirt with tights and a blazer. For a date night, switch to a chic blouse to complement the boots and skirt. The options are endless with this combination.

Knee High Boot Outfits

Knee High Boots & Slip Dress or Slip Skirt

Pairing knee high boots with a slip dress or skirt is effortlessly chic and timeless. I love wearing my brown knee high boots with a matching brown slip dress and then adding a blazer for a classy look. Another go-to is a navy outfit with my brown knee high boots, a slip skirt, and a sweater. It’s simple, elegant, and always in style. There are so many gorgeous options for styling this combination.

Knee High Boots & Lace Dress Outfit Idea

Knee High Boots & Lace Dress Outfit Idea

Black knee high boots paired with a white lace dress create a stunning outfit that works for everything from office wear to date nights. Adding a black belt and a matching bag, like this one I love from DeMellier, ties the whole look together perfectly. Also, for more style tips and why I adore this bag, make sure to check out my DeMellier bag review.

Knee High Boot and Short Dress Outfit Ideas

Styling knee high boots with a short dress is a flattering combo that I adore for nice occasions from a chic lunch with friends to date night and more. The tan boots give a sleek vibe, especially when paired with a ruffled cream or white dress. Then, just add matching accessories, like a tan bag and sunglasses and you’re all set for any event.

Knee High Boots and Sweater Dress

Pairing knee high boots and a sweater dress make up one of my favorite outfits, especially for cooler weather. I love pairing my brown knee high boots with neutral colored sweater dresses in tan or gray. Also, for a sleek, monochromatic look, I match my black boots with a black sweater dress. This combo is perfect for work, lunch meetings, and more, offering both comfort and style.

Knee High Boots and Pencil Skirt Outfit

Another favorite outfit of mine is pairing knee high boots with a pencil skirt, creating a chic and elegant look. This combination is perfect for the office, date nights, and beyond, offering a sophisticated vibe that’s both stylish and professional. If you’re going for an all black outfit, opt for black knee high boots to keep it monochromatic.

With a Statement Wool Coat

Pairing knee high boots with a statement coat, like a wool coat, is a fantastic way to stay warm while dressing up your outfit. I enjoy coordinating my boots with my coat for a cohesive, monochromatic look. Overall, this style is ideal for elevating your winter wardrobe, perfect for any occasion from casual outings to more formal events.

Best Knee High Boots

Sharing some of my favorite knee high boots. Simply click on each image to shop.

Don’t forget to pin to save for later!

Knee High Boots Outfit Ideas

Check out my latest posts for more classy style inspiration!

Please feel free to email me at if you have any questions!  I’m always happy to help with styling or picking out a specific outfit for an event!   Have an amazing day!!

Also, check out my instagram shop HERE to shop all my instagram looks, style guides, gift guides and fashion tips.

You can also download the free LIKETOKNOW.IT app and follow me HERE.

STAY IN THE KNOW:  Don’t forget to sign up for my exclusive Newsletter for STYLE TIPS, SALE ALERTS, AND MUCH MORE!

As always, thank you so much for stopping by today, I truly appreciate all of you! xx, Amanda


Instagram | Pinterest | Facebook | Shop Instagram | You Tube

Leave a Comment


Subscribe to my newsletter for new blog posts, sale alerts and more!