In my book, knee-high boots are timeless. Even though styling knee-high boots from year to year can change, they always have the potential to be the statement piece of your overall look. Knee-high boots typically have their biggest moment in the fall and winter months, but there are certainly ways to style knee-high boots in the spring and summer as well.

The Nordstrom Anniversary Sale is a great time to snag new and stylish knee-high boots on sale for the upcoming season. Today, I’m rounding up outfits that you can wear with knee-high boots throughout the seasons. Let’s jump in!

20 Knee-High Boots Outfit Ideas

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How To Style Knee-High Boots

Styling knee-high boots can “box” you into certain pieces in your closet, like only pairing them with leggings or skinny jeans. But I’m here to challenge you to branch out! Personally, my favorite way to wear knee-high boots is with a midi dress. If I’m feeling up for it, I’ll even add a hat and a sweater to step up the look. There are endless ways to style knee-high boots, and this just might be your sign to try something new.

Mini Dress

As I confessed, adding knee-high boots to a mini dress is one of my favorite ways to style them. To accessorize the look, I like to add pieces like an oversized sweater, a hat, or a light sweater. You could also add a jean jacket or a leather jacket, depending on the dress. Knee-high boots also go well with a mini sweater dress or a mini shirt dress, too. In the colder months, you might find me in a sweater dress with suede boots.

Midi Dress

Wearing a midi dress is certainly one of my favorite ways to wear knee-high boots with a dress. There’s just something about the look of a midi dress covering the top of your boots but still showing the boot where it hits your ankles and below that is so classy. In the winter, I love to add a long coat to this knee-high boots outfit and I’m out the door.

Mini Skirt

Similar to the look of a mini dress, adding boots to an outfit with a mini skirt is another great way to style tall boots. Whether you’re pairing your boots with a structured skirt, a flowing skirt, or a knit skirt, knee-high boots have the potential to go with them all.

Midi Skirt

Midi skirts are a great option for styling knee-high boots. There are also several different types of midi skirts that go with tall boots. Skirts such as wrap skirts, pleated skirts, or satin skirts. Depending on the color and fabric of both the skirt and the boots, there is certainly potential to match tall boots with your favorite midi skirt.


For a go-to easy winter outfit that will still have you feeling put together, pair your knee-high boots with faux leather leggings. I promise this combination is a match made in easy outfit heaven! The best part about styling boots with faux leather leggings is that there are several options for what to add on top – you could spring for the even loyal oversized sweater, but you can also add a blouse or a button-down shirt.


Last but certainly not least, I’m sure you can agree that knee-high boots with jeans is a winter staple. Skinny-leg jeans pair well with both your knee-high boots and thigh-high boots, too. If you have a pair of straight-leg jeans and a pair of knee-high boots that are a little on the wider side, those two pieces could create an on-trend look as well.

For styling tall boots that will get you through potential weather, see my Hunter Boots Review post!

Knee-High Boots with a Mini Dress

Pairing tall boots with a flowing, colorful mini dress can create a great season transitional look. Whether you’re going from fall to winter, or winter to spring, tall boots with a mini dress can take you there.

Adding these square-toed boots to this mini-dress look made me instantly grab my hat to finish off the outfit. I love the way these square-toed boots add a unique touch to the flow of this floral mini-dress.

For a more straight-style mini dress, I like to add a pointed knee-high boot to add length to the overall look. The long sleeves and the tie-up detail on this dress pair well with the straight look on the bottom that’s created by these tall boots.

Knee-High Boots with a Midi Dress and Sweater

To me, an oversized sweater with a mini dress underneath and knee-high boots is always a match! I love that this look can help you move through the seasons and changing weather, from hot to cold or cold to hot. You could easily remove the sweater and tie it around your waist if you got too warm.

An oversized sweater pairs well with a straight mini dress and knee-high boots, too! For this neutral-on-neutral look, I added a neutral hat to add another element and elevate the overall outfit.

Another way to wear a mini dress with tall boots is to add a light sweater or cardigan on top. You might not need the extra layer for warmth, but adding another layer can create another dimension to the look if you want to switch it up.

Knee-High Boots with a Midi Dress

For winter, consider pairing your knee-high boots with a midi sweater dress for an outfit with ultimate style and warmth. I love the way these dark boots complement the dark tones of the belt on this dress. Don’t be afraid of the contrast that comes with pairing darker boots with a light-colored or white midi dress!

A knit black dress with tan knee-high boots is a look that I hope never goes out of style. It’s too easy and so chic every time! This is an outfit that I would style in so many ways – workwear, date night, or a night out grabbing a drink with girlfriends, this look works for several occasions.

Knee-high boots pair well with flowing midi dresses, too! I love how the pointed toe on these boots adds length to the overall look and balances out the flow of the dress. The tan in the boots also pulls out the colors of the floral pattern as well. Depending on the occasion and the season, I would add a jean jacket or a long coat.

Knee-High Boots with a Mini Skirt

To take your mini skirts into colder seasons, add knee-high boots to create an outfit that will help you stay warm. Add boots with a pointed toe to complement the flair of an a-line skirt like this one.

Knee-high boots pair well with knit mini skirts as well. To add an extra element and tie together the neutrals in this look, I added a long scarf with a neutral-colored pattern. I love the lines that the pointed toe and heel on the boot add to this outfit.

Heeled knee-high boots with a sequined skirt are a yes for me. To add balance, consider adding a neutral-colored boot to compliment a bold element, like sequins, to your mini skirt look.

Knee-High Boots with a Midi Skirt

When pairing tall boots with a midi skirt, make sure that the height of your boots is a good match for the length of your skirt. You wouldn’t want your skirt getting caught up in your boots, or being a length that doesn’t match up. Like pictured in this outfit, ensure that your skirt can fully cover the top of your boots with a few extra inches for walking and standing.

If your midi skirt is longer, I recommend going with a tall boot with a pointed toe and at least a slight heel to lengthen the overall look! I love the tone-on-tone of these light tan boots with a cream-colored skirt and a chunky knit sweater for winter style.

Don’t be afraid to style a wrap skirt with your knee-high boots! As I mentioned above, I would ensure that the length of your wrap skirt pairs well with the height of your boots. If the opening of your wrap skirt goes above the boot, try to wrap your skirt in such a way where that wouldn’t cause an issue with your outfit.

Knee-High Boots with Leggings

This is a look I can see myself recreating for a long time. Effortless, comfortable, and so chic. Pairing a white button-down with my favorite faux leather leggings and my dark brown tall boots was easy to throw on for the day. I added this black bow to tie half of my hair back and I loved the way this outfit came together.

Light-colored knee-high boots like this pair can also be paired with your leggings as well. I added a blouse and a hat to this look and called it a day. This look took me from summer into the cooler breeze of fall.

Here’s to hoping that oversized sweaters and leggings never go out of style. I added a pair of dark brown pointed-toe tall boots to elevate this look and tie in the dark brown of my bag.

Knee-High Boots with Jeans

Knee-high boots pair extremely well with blazers, too! Although blazers are on trend at the moment, they will always be a great piece to pair with your tall boots to create an outfit.

And for the cherry on top, I styled my high-heeled knee-high boots with the classic oversized sweater and skinny jeans. Is there anything better? Pointed-toe tall boots certainly elevate this look for dinner or an evening out in the cooler months of the year.

What was your favorite way to style knee-high boots from this post? Let me know in the comments below!



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