Knee-high boots are one of my wardrobe essentials in the cold months, especially with dresses. I’ve tried all sorts of boots with dresses, but I always land on styles with a tall shaft so that the hem of the dress covers the bottom of the boots. Not only is the combination fairly easy to style, but it’s practical for warmth, can make an outfit feel proportional, and is timelessly stylish.

I have a few well-loved tall boots I’ve collected over the years in various colors and different heel heights, from this block heel leather pair that goes with everything (I have both black and brown) to this comfortable riding boot and this dressy stiletto boot. I also have my leather tall riding boots, which I always clean and polish using URAD products to keep them in good condition.

Below, I wanted to share how to wear knee-high boots with dresses, answer common styling questions this combination, and share the tall boots I can vouch for in case you’re in the market for a new pair.

How to Wear Knee-High Boots with Dresses

The right knee-high boots outfit always starts with choosing the right boot, which involves consideration of style, heel height and shape, width, material, color, and details, like toe shape, buckles, and ties.

There’s no secret sauce when it comes to styling boots with dresses, but two things to keep in mind are the rule of thirds for balance and picking boots that match the occasion. I group my tall boots in three categories: casual (flat/riding), versatile (block/kitten heel), and dressy (stiletto). When it comes to what dresses to wear with knee high boots outfits, mini, midi, and maxi are all game as you’ll see below!

9 Knee-High Boots with Dress Outfits

With a Midi Dress

Similar Dress / Knee-High Boots

This is my favorite fail-proof dress and tall boots combination. I try to match the style of the boot to the style of the dress. For example, an evening dress with a stiletto and a casual boot with a shirt dress. For this floral dress, I chose a block heel boot with an almond toe to complement the feminine feel. I’ve searched high and low for the best fall boots, and as far as classic boots go, my favorites are the Loeffler Randall Goldy. I have them in black and brown, and they run true to size. While an investment, I think they’re worth it! They go with dresses, skinny jeans, skirts, leather shorts, and more.

With Tights and a Mini Dress

Dress / Tights / Knee High Boots

You can also wear knee-high boots with a mini dress. Although I see people wearing them without tights, I appreciate how sheer tights cut back on the contrast between the boots and my skin, helping with leg lengthening. I love Falke tights. They add warmth without making the outfit feel heavy. I keep the rule of thirds in mind by choosing mini dresses that cinch at the waist for added shape and that hit several inches above the knee. I would also wear this look with a mini skirt (anything too long will give the legs a shorter appearance).

With a Tights, a Mini Dress, and a Coat

Mini Dress / Coat / Tights / Similar Boots

This is a twist on the above for cold weather. When wearing knee-high boots with a mini dress, I love a cropped coat like this Reformation coat to accentuate my waist. You could also opt for a long coat that hits between the bottom hem of the dress and the top of the boot, or a maxi coat that falls past the top of the boot. This Paige dress is the perfect fall mini, with an autumnal colorway, long sleeves, and a tie waist.

With a Sweater Dress

Dress (Similar Dress) / Knee-High Boots

This sweater dress outfit shows off the versatility of a classic block heel boot (these are the same Loeffler Randall boots mentioned above). If you want to elevate a knit dress, leather boots are a great way to do that. I love this combo for Thanksgiving, date night, or a special dinner. To make it even dressier, I’d swap the block heel for stiletto boots.

With a Sweater Dress and a Faux Fur Vest

Similar Vest / Similar Sweater Dress Here and Here / Knee-High Boots

I absolutely love this combination for cold days when I want to be put together and comfortable. Faux fur always feels a little elevated, and opting for a vest allows the sweater dress to shine through. The leather boots add contrast agains the white. I wore this outfit for holiday photos and received so many compliments!

With a Short Black Sweater Dress

Similar Sweater Dress / Similar Boots / Similar Bag

You can also style knee-high boots with a short black sweater dress. Similar to a mini dress and boots, I like to choose a short sweater dress that hits well above the knee to give the illusion of length to my legs. I’m wearing an old Everlane dress, but this similar style is available this year.

With a Short White Sweater Dress

Similar Coat Here and Here / Sweater Dress / Similar Boots / Similar Bag Here and Here

This look is nearly identical to the above but with a chunkier turtleneck sweater dress. The sweater dress pictured is one of my best Amazon finds ever, and it also goes well with OTK boots too, which you can see in this over the knee boots outfit roundup post.

With a Popover and a Dress

Popover / Dress / Similar Boots / Earrings

This is a fun and unexpected look if you have a popover sweater in your wardrobe. Mine is by Marie Oliver (also available in cream) and has cable knitting for a cozy, textural finish. It adds warmth to the torso when it’s too chilly to wear a long sleeve midi like the Doen dress I’m wearing alone. The boots are the same Loeffler Randall knee-high boots in cognac.

Evening and Heeled Boots

Similar Dress (Exact Dress Available in Blue and Black) / Similar Boots / Bag

For date night, girls’ night out, a show, or a special event, I love heeled knee-high boots paired with a dress in an elevated fabric like silk, chiffon velvet, and lace. I think a stiletto heel is best but a block heel boot with a slim shaft can also work. I try to avoid wide shafts for nicer dresses as they can add bulk under delicate fabrics. Both leather and suede boots work, but I like to choose the texture that contrasts the dress. For example, leather boots would look better with a velvet dress than suede. You could also style a short sleeve slip dress with a stiletto boot and an oversized sweater for a dressy but cozy layered look.