Fall style is all about layers and boots, so if you haven’t yet, now is the time to pull out your knee high boots!
Wearing them with skinny jeans is always an easy go to outfit but if you want to dress things up, here are 15+ ideas on what dresses to wear with knee high boots.
This post contains affiliate links. By using my links to shop I may receive a small commission. Thank you for your support!
Knee high boots paired with dresses create the perfect fall outfits. You feel put stylish, put together and appropriate for the ups and downs of the weather. There are so many different styles of dresses that really look great with knee high boots!
If you are looking for ideas on what dresses to wear with knee high boots, keep reading for lots of inspiration on what to wear!
Adding tall boots, cute/cozy layers and accessories can even turn some of your favorite dresses during warmer months into Fall ready looks.
Here are some previous ways that I have styled classic knee-high boots:
Ruched Bodycon Dress with Knee High Boots
I have this style of dress in multiple different colors and absolutely love it. It is flattering on every body type with the ruching detail, and when paired with tall boots it really feels effortlessly pulled together.
I styled the black ruched dress with black boots and layered different cardigans for a cozy touch. This is a great way for a way to wear a black outfit, without wearing all black.
Drop Waist Dress with Tall Boots
I love the drop waist silhouette style of dresses and they look amazing with thigh-high boots! I paired my dainty floral printed dress with tan boots, a neutral colored cardigan and a pom knit hat.
This is definitely the kind of outfit I would wear all season long. This is a stylish look that would be perfect for all of the Fun fall activities!
Shop dropwaist dresses to wear with boots
Floral Mini Dress with Over the Knee Boots
The older I get the more I really try to make use of the items I have in my closet. Floral dresses are something I wear a lot during the Spring/Summer but they are a great option for Fall as well!
When paired with over the knee boots and cozy layers, your pretty floral dress turns into the cutest Fall look.
I paired mine here with a coat but this look would also be so cute with a blazer or even a chunky knit worn over the dress to give the appearance as if you’re wearing a skirt.
shop floral mini dresses
Outfit inspiration for dresses and knee high boots
Here are some more different outfits and different styles of dresses that would look great with knee high boots! These are definitely on my list to recreate this season.
Flowy Dress with knee high boots:
I am absolutely obsessed with this look! I love the flowy white dress paired with the brown boots. This is the perfect example of your pretty white summer dresses being able to be re-worn in different seasons!
This look would be so cute for family photos or a girls night in the fall. A pair of knee-high boots is a fall staple for all occasions.
Off Shoulder Dress with Knee Boots:
I always love the look of long sleeve off shoulder dresses as I think they are so flattering with the pop of skin. This outfit ideas would be a great option for a fall date night outfit. It looks so cute with the tan boots and I think would also look great with slouchy boots as well.
What a great way to transition to your winter wardrobe as well, with the layering of the scarf. Just add a cozy warm coat and you are set!
T-shirt dress with knee high boots:
What a great casual look! A t-shirt dress is a wardrobe staple! Most of us already have one in our closet and I typically wear mine during the spring or summer but I saw this idea to pair the t-shirt dress with knee high boots and I just love it!
It looks great with a belt around the waist and the pop of the white boots. This is so stylish and on trend for the season. Another outfit idea for the white boots would be a an oversized sweater with denim jeans!
A-line dress with knee high boots:
Another great way to style dress from warmer months for fall. These a-line dresses are so cute and I love it paired with the tan hat and boots.
This would be cute in all different colors and would even look great paired with black tights and black boots for a more dressed up feel. This dress would be cute paired with different type of boots from ankle boots to over the knee boots and even combat boots!
Embroidered dress with knee high boots:
For a boho feel – try pairing an embroidered dress with slouchy knee-high suede boots! This is on the top of my list for an outfit to recreate and the perfect casual outfit for the season and for everyday wear.
What a fun look for Fall family photos and Fall activities. If it’s chillier, just layer with a long coat!
Lace dress with knee high boots:
The perfect date night or co*cktail party all black look! A lace black dress is a closet staple for me and I just love the feminine look with the over the knee boots.
It looks so ute styled with a black leather jacket/moto jacket as seen above and I think it’d also look great with a long blazer for a work event.
Blazer dress with knee high boots:
Do you love the current trend of blazer dresses as much as I do?! This whole look is so stylish and I really love the neutral color palette.
You could recreate this same look with different colors, such as a black blazer and black over the knee boots, or a colorful blazer and tan boots. The options are endless!
Blazer dress with knee high boots:
Shirt dresses are another wardrobe staple in my mind and you really can style them so many different ways. Wear them on their own, layered with the cute pullover or chunky knit, or top with a cute jacket. It’s a cute way to wear a dress that looks like a mini skirt but isn’t!
The shirtdress paired with white boots is such a pretty and unexpected look for Fall. This is something I definitely am going to recreate myself this season. I think this kind of outfit would be a great option for work or dinner out. It feels chic and feminine.
Skater dress with knee high boots:
Skater dresses have such a flirty feel and this a great option to add a feminine look to your knee high boots! I love it paired with the big chunky plaid scarf to add different textures, or as an easy way you could wear it on it’s own with a chunky necklace.
This kind of outfit could be worn to so many different occasions/events and is a go-to Fall outfit for me. Skater dresses look great on all body types and also look so cute styled with tights for cooler months!
Midi length knit dress with knee high boots:
This is a great comfortable look, yet still so chic. Midi-length dresses are great for petite ladies. If you are on the shorter side, maxi lengths can typically be too long.
This knit midi length dress with knee high boots is such a chic look!! I love the black leather boots to contrast off the knit style but really most boot styles would work with this outfit.
If you don’t have a knit dress you could always recreate something similar with knit pencil skirts and a sweater tucked into it! This look would be cute with ankle boots as well.
Bodycon dress with knee high boots:
If you’re looking to wear knee high boots for date night I think a body con dress and a long cardigan is the best choice! It is sexy but still cute and cozy and really flattering. I love it styled like the above with all black and the white sweater. A black dress is always my go to for date night and it is just such an easy way to be dressed up for a night out while still being comfortable!
Sweater dress with knee high boots:
If you don’t have a great sweater dress that you love that is one essential piece I think every woman needs for Fall/winter and it is my favorite way to wear knee high boots! You could create this look with an oversized knit sweater as well!
The chunky knit instantly gives me fall feels and is truly the perfect fall pairing. You can layer it with a long coat, a long cardigan, a moto jacket, flannel shirt or just on it’s own! I love the all neutral color palette shown above.
I hope this helped provide inspiration with what dresses to wear with knee high boots!
