I 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 a pair of knee high boots 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, 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.
What To Wear With Knee High Boots
Knee High Boots with Skinny Jeans
Coat (similar) | Sweater (similar) | Jeans (similar) | Boots | Bag (similar) | Sunglasses
Sweater (similar) | Jeans (similar) | Boots | Bag (similar) | 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 Slip Skirt
Vest (similar) | Turtleneck | Skirt | Boots (similar) | Bag (similar) | 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
Dress (similar) | Boots (similar) | Bag (similar) | Sunglasses
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 Short Dresses
Dress (similar) | Boots (similar) | Bag | Sunglasses
Dress | 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.
Knee High Boots with Dress Shorts
Coat (similar) | Sweater (similar) | Shorts (similar) | Boots (similar) | Sunglasses
This is definitely a more fashion forward way to style knee high boots but one that I will forever love. The best kind of shorts to wear with knee high boots are dressier shorts, something like this high-waisted style I am wearing in the above photo. Make sure the shorts are at least mid-thigh length but not a bermuda length that goes all the way to the knees. You want a bit of leg to show in order to balance out the outfit proportions.
Knee High Boots with Straight Leg Jeans
Coat | Jeans | Boots | Bag | Sunglasses
It is possible to style your straight leg jeans with knee high boots but it is definitely a bulkier look. You need to make sure your boots are wide enough to fit the extra fabric from the straight leg denim but this is a nice modern and updated way to style your denim with knee high boots without only wearing skinny jeans. The jeans may naturally bunch around the knees which is fine but trying to do this look with any jeans wider than straight leg may not work as well.
Outfits with Suede Knee High Boots
Dress | Boots | Bag (similar) | Sunglasses
Dress | Boots | Bag (similar) | Sunglasses
Suede boots are my preferred fabric if I had to choose between that and leather. I feel like suede instantly looks polished and more luxe. It’s a fabric that you can wear with any outfit regardless of the material or texture of the clothing you are pairing with it.
How to Style Knee High Boots
Slim Fitting Pants/Jeans
If you plan on tucking your pants or jeans into your boots, it’s best to do that with slim fitting styles. Anything too bulky won’t fit easily into your boot.
Midi/Maxi Dresses and Skirts
I always like to choose knee high boots over ankle boots when I’m wearing them with midi or maxi skirts. Even if the skirt or dress looks long enough to cover the top of the ankle boot, it’s better to not have any gap or skin showing so there is one continuous line from the top to the bottom of the outfit.
Short Dresses
Short dresses will always be a great option to wear with knee high boots but the key is balancing out the proportions properly. If the dress is above mid thigh, opt for a boot with a lower heel. If the dress is closer to the knee or right above, choosing a higher heel actually creates a better silhouette.
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