Our 9 Fave Dresses To Wear With Knee-High Boots

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There’s no shortage of love for knee-high boots from our side! Here’s a style guide on our favorite dresses to wear with knee-high boots.

If you’ve never had a pair of knee-high boots in your life, you’ve got to get on the bandwagon now. There are so many different outfits you can create with these boots, whether you’re pairing them with skinny jeans, your favorite mini skirt + oversized sweater combo, shorts, leggings, or dresses.

They’re a serious closet staple during the colder months, and it’s easy to see why. They can take any outfit from drab to fab and add a touch of style and sophistication.

White mini dress with tan cowboy knee high boots
Get this dress on Princess Polly

Now, we’ve already mentioned that they’re easy to wear with almost anything, but one of our favorite garments to style with these boots are dresses. While sweater dresses are the classic go-to piece to style with knee-high boots, there are so many other options to choose from in addition to that.

Below, we’ve put together a list of our 9 favorite dresses to wear with knee-high boots. Whether you’re looking for a dress to wear to work or a dress to wear out on the town, we’ve got you covered. Keep reading for our top picks as well as our favorite knee-high boots outfits.

The Best Dresses To Wear With Knee-High Boots

1. Sweater Dresses

Sweater dresses are comfortable and stylish, and they are an absolute favorite, especially during the winter months. We love pairing them with knee-high boots and a cute scarf or a long coat for the perfect fall outfit.

Wear a cream-colored sweater dress with a pair of white or tan boots with a block heel for ultimate comfort. For a stylish look, accessorize with a designer handbag of your choice.

2. Flowy Dresses

The Best Dresses To Wear With Knee High Boots: Flowy black floral mini dress
Get this dress on Magnolia Boutique

Flowy dresses are always a great choice to pair with knee-high boots, especially during the cooler months. This outfit is perfect for a day of running errands or lunch with friends.

You can wear this look as it is, or you can also add in a black leather jacket or a trendy long coat and a fedora hat for when the weather gets a little chilly. This is such a cute look that’s perfect for everyday wear!

3. Classic LBDs

Ah, yes, the classic LBD. A little black dress is always a good idea, and it looks even better when worn with a pair black knee-high boots. This outfit is perfect for a night out on the town or a date night. Just add a touch of jewelry and you’re good to go!

When the weather is chilly, simply wear your dress with a trench coat or a long cardigan.

4. Blazer Dresses

Looking for a chic Parisian outfit? Blazer dresses are ideal for evening events where you want to make a great impression, but they also work well for daytime outfits. They convey confidence and professionalism, and they look great with knee-high boots.

Just add a pair of earrings, a designer handbag, and you’re all set – you’ll look like walking down the runway of your very own fashion week!

5. Empire Waist Dresses

The Best Dresses To Wear With Knee High Boots: Light pink empire waist mini dress
Get this dress on Magnolia Boutique

Dresses with an empire waist are incredibly flattering (especially on a pear-shaped body type), and they also look great with knee-high boots. If you’re looking for a dress to wear to a holiday party or family gathering, this is the perfect option for an incredibly feminine and elegant look.

6. Floral Dresses

The Best Dresses To Wear With Knee High Boots: Floral mini dress with long sleeves
Get this dress on Magnolia Boutique

When it comes to cute dresses, floral print dresses are always on top of the list. Floral dresses are perfect for the warmer months, but they can also be worn in the fall and winter.

Pairing a floral dress with knee-high boots is a great way to transition your wardrobe from one season to the next, especially during springtime. For added femininity, you can also go for off-shoulder dresses if the weather permits.

7. Bodycon Dresses

The Best Dresses To Wear With Knee High Boots: Burgundy bodycon mini dress
Get this dress on Lulus

Bodycon dresses are sultry and stylish, and they look fabulous when paired with knee-high boots. Depending on your dress, this can be a great look for a party, or you can wear the combination out and about during the day – just make sure to accessorize the look with a long coat or oversized blazer and a stylish bag to keep the look classy.

8. Shirt Dresses

Oversized t-shirt dress
Get this oversized t-shirt dress on Urban Outfitters

Ariana Grande is famously known for her tall boots + oversized outfits combo, so if you’re trying to embody her style in your own unique way, why not opt for an oversized t-shirt dress with your knee-high boots?

Shirt dresses are versatile and easy to wear, which makes this outfit perfect for running errands or grabbing coffee with friends. Plus, if you have a pair of flat knee-high boots, you can even wear this look to a music festival! Simply accessorize with a belt bag or a waist belt, so you won’t look super boxy.

9. Denim Dresses

The Best Dresses To Wear With Knee High Boots: Denim chambray dress
Get this dress on Pink Lily

Denim dresses are comfortable and casual, and they can be dressed up or down depending on your mood. Denim blue pairs well with cream and camel-colored knee-high boots for a casual but cute fall look. If it’s slightly colder in your area, you can also throw on a matching chunky scarf to keep you warm.


And there you have it, these were our top 9 picks for dresses to wear with knee-high boots. We hope you found a few new different ways to style your boots and that you’ll be able to put together some cute outfits for the upcoming season.

If you’re still looking for more fashion inspiration, check the posts down below.

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