Knee High Boot OutfitsI will forever be a knee high boot fan. Even more than ankle boots, I tend to gravitate towards knee high boots and how they can look so chic with a ton of different looks. And they are more versatile than ankle boots because they can be worn under jeans/trousers and look like an ankle boot and then also still be styled with short dresses and skirts too. I don’t always love the look of ankle boots with a shorter dress/skirt as I find it’s not as flattering and can make my legs look a bit shorter.

It’s great to buy colorful, trendy or unique knee high boots (I still love the combat boots trend), but my preference will always be a simple pointy toe style in a neutral tone. I have both suede and leather in my closet and love both, though I always think suede looks a tad more elevated and polished. Especially in fall and winter when the added warmth is needed, knee high boots are a must have.

10 Knee High Boot Outfits

When choosing a knee high boot, I always prefer for a simple style with little to no details on them so as not to compete with my outfit. A pointy toe is also my preferred toe shape because it lengthens the leg and is a classic style that will can be worn over and over each season. A simple pointy toe boot will never go out of style and is something you can count on wearing for many years. If you want something with no heel, I love the look of riding boots. They can be simple and classic but still give you a chic polished look.  I’ve styled knee high boots a ton of different ways over the years and am rounding up a bunch of different looks to give you some inspiration on how to style your own knee high boots.

Knee High Boots with Skinny Jeans

Knee High Boot Outfit ideasCoat (similar) | Sweater | Jeans | Boots | Bag | Sunglasses

Knee High Boots Outfit ideasBlazer (similar) | Shirt (similar) | Jeans (similar) | Boots (similar) | Bag (similar) | Sunglasses

Knee High Boots with jeansSweater | Jeans | Boots | Bag | Sunglasses

I know skinny jeans have taken a back seat at the moment and straight leg/wide leg jeans are front and center but skinny jeans are still the best denim to wear with knee high boots. While you can tuck straight leg jeans into knee high boots, I don’t love the look as much as a skinny jean. When balancing out proportions for a skinny jean outfit, I will often keep the upper part of my look a bit more oversized. Wearing a super skinny top with super skinny jeans can be too much so balance out the look with a chunky sweater or slightly roomy blazer. Also a button down blouse would work well too as I have shown in the photo with the brown blazer.

Knee High Boots with Midi Skirts

Knee High Boots with Midi SkirtsVest (similar) | Turtleneck | Skirt (similar) | Boots | Bag (similar) | Sunglasses

Knee High Boots with Midi Skirt outfitTurtleneck | Skirt | Boots | Bag | Sunglasses

This is a perfect example of why I will always opt for a knee high boot over an ankle boot when shopping. When wearing a midi skirt, I like the skirt to go past the boot and create a longer silhouette. And if there is a high slit in the front like with the denim skirt I am wearing, a knee high boot works so much better than an ankle boot. An ankle boot cuts off the line of the outfit and can make the legs look shorter.

Knee High Boots Styled with a Dress with Slits

Knee High Boots Styled with a Dress with SlitsDress | Boots (similar) | Bag | Sunglasses

slit dress and knee high boots outfitDress | Boots (similar) | Bag

Especially during the fall and winter, wearing knee high boots with a dress that has a high slit is necessary. It will help keep your legs warm LOL but balances out the slit only allowing for a small bit of leg to show.

Knee High Boots with Leggings

Knee High Boot Outfits with leggingsSweater (similar) | Leggings | Boots (similar)

Since the silhouette of leggings is the same as that of skinny jeans, I will often style them the same way when wearing knee high boots. I opt for something looser or more oversized on the top to balance out the fitted shape of the leggings. If I had to choose between wearing leggings or skinny jeans with knee high boots, I would go for skinny jeans because they are a tad less casual and look better with a dressier type of knee high boot.

Knee High Boots with Short Dresses

Knee High Boot Outfits with short dressesDress | Boots

short dress and boots outfitJacket (similar) | Dress (similar) | Boots

sweater dress with knee high bootsDress | Boots (similar) | Bag | Sunglasses

short sweater dress outfitDress | Boots (similar) | Headband (similar) | Bag (similar)

A classic way to style boots is always with a shorter dress or mini skirt. I love the way this looks! For me the key to making this look polished and elevated still is to choose a slim fitting boot with a pointier toe. It looks more refined and understated and is easy to pair with a short sweater dress or skirt.

Another tip is to choose a skirt/dress length that hits above the knee. There needs to be a slight gap between where the boot ends and where the dress begins to balance out the look. Wearing knee high boots with a skirt or dress that hits exactly at the knee or slightly lower can be difficult to style. I prefer to either go with a midi length that completely covers the top of the boot and creates on seamless line or a shorter style which allows for the boot to be fully shown.