Build your own wardrobe

How to Style & Wear Boots

Over-the-knee boots, knee-high boots, ankle boots, I love them ALL. I wish Houston weather would allow me to get more wear out of mine, but I will take what I can get. Now, let’s dive right into everything we need to know about boots. How to style and wear boots, and everything in between.

Which, BTW- make sure to scroll ALL the way down in this post where I’m sharing how to style and wear ankle boots with denim. I’m telling you, we are covering it ALL ?. 

Over the Knee Boots

Elly Brown wears over the knee boot with a faux leather skirt
Elly Brown wears over the knee boot with a leopard dress and trench coat
Elly Brown wears over the knee boot with a floral dress and a leather jacket

outfit details:
LEFT OUTFIT: Top // Skirt // Boots
MIDDLE OUTFIT: Coat // Dress (Similar) // Hat // Purse // Boots
RIGHT OUTFIT: Jacket // Dress // Boots


Let’s start with over-the-knee boots. Some may argue these are out of style and outdated. I beg to differ. Remember, and I may say this in every single post, and you may get tired of reading this… but at the end of the day, where what you want. I am only here to help guide you and share my tips and how I style things. Style is unique, and what I like you may not like, and vice versa. There is nothing wrong with that.

Back to OTK boots. I love how they make your legs appear longer. Also, they look stunning with skinny jeans, and if you want to wear a dress but want some warmth for your legs, I feel like these are an excellent option. I have a pointy toe because I want to dress them up, and I think a pointed toe shoe is more posh and polished.

Knee High Boots

Elly Brown wears knee high boot with a zara pleated dress and tweed blazer
Elly Brown wears knee high boot with a denim skirt and Revolve fringe sweater
Elly Brown wears knee high boot for an monochromatic brown look

outfit details:
LEFT OUTFIT: Dress (similar) // Jacket (Similar) // Boots
MIDDLE OUTFIT: Sweater // Skirt (Similar) // Purse // Boots
RIGHT OUTFIT: Coat // Sweater // Skirt // Purse // Boots


Knee-high boots may be my favorite, and I’m going to be honest here, you don’t need all these different boots. Look at your closet and access what works best for you and your lifestyle at the end of the day. Then go from there. But I think knee-high boots are the most versatile boots to own. They look GORGEOUS with dresses, pants, skirts, and you name it. Sam Edelman has some excellent quality knee-high boots. Aldo boots are also excellent. My croc boots are almost four years old and from Aldo.

Also, note… when buying boots, I would look at your closet and the colors you have, then decide what color boot to get. I would stick to black/brown, maybe grey or blue. Start with black, though.

Sock Booties

Elly Brown wears Aldo sock bootie with a sweater vest

Elly Brown wears a sock bootie with a leather jacket and bodycon dress
Elly Brown wears Aldo sock bootie with leather pants and a tweed blazer

outfit details:
LEFT OUTFIT: Dress // Sweater (Similar) // Boots
MIDDLE OUTFIT: Jacket // Dress (Similar) // Boots
RIGHT OUTFIT: Jacket (Similar) // Shirt // Pants // Boots


Sock booties are technically a version of ankle boots, but I want to highlight them on their own here, only because I LOVE the one I recently got from Aldo. It’s a versatile boot, and I actually think sock booties are more versatile when it comes to wearing them denim and pants. See below how I styled them with 4 different pants

Ankle Boots

Elly Brown wears a white ankle boot for an all white monochromatic look
Elly Brown wears ankle boots with a lace dress and utility jacket
Elly Brown wears combat  boots with stockings and a floral dress

outfit details:
LEFT OUTFIT: Coat // Dress // Purse // Boots
MIDDLE OUTFIT: Dress // Jacket (Similar) // Belt // Boots
RIGHT OUTFIT: Dress // Stockings // Boots


Finally, we have ankle boots. From combat boots to everything else that’s around your ankle ?. These can be a bit more tricky to wear with your pants or denim but can still be done. Depending on the shaft height of the boot also, I don’t love true ankle booties with dresses. I think they can cut off your leg in a weird way. My workaround is to either visually wear longer dresses to draw the eyes down or wear the same color tights as I did with my combat boots above.

Unpopular opinion here also, I don’t like the ankle cutout bootie (don’t come for me ??‍♀️☠️). But, see, remember style is unique to each, and it’s all okay!

Elly brown shares how to style ankle boots with cropped pants

Tip: Same pants, same shoes. The difference here is the length of the pants. For most body types with any ankle bootie, your pants should be cropped right above your ankle. 

Elly brown shares how to style ankle boots with cropped leather pants


Here are two different types of pants with different boots. Sock booties typically look best worn UNDER your pants, UNLESS they are skinny jeans (both over and under skinny jeans look good). For true ankle booties, pant hem should hit right above the boot (see below how to crop if they are longer). If your boot is knee-high, OTK, or has a higher shaft, always tuck inside pants inside your boot. 


Elly brown shares how to style ankle boots with cropped denim

To cuff or not to cuff? At the end of the day, I think it will come down to personal preference. My opinion? For someone who is borderline petite (I’m 5’3), I would not. Cuffing can look bulky and add unnecessary weight to your legs, and unless you cuff them juuuuust right, it can cut off your legs, making you look shorter. If you need to cuff, I would only cuff your skinny jeans and cuff OUTSIDE IN (just like I did in the right side image with the peep-toe bootie and skinny black jeans).

Elly brown shares how to style ankle boots with cropped jeans

Before I forget too, round vs. pointy toe; which one is better? Again, I think that will be a personal choice. Both are classics and there is no right or wrong answer. For me, pointy-toe tends to be a bit dressier vs round-toe tends to be a bit more casual (not always the case, but as a general rule). I think it’s great to have a mixture of both so you can have it all but without having 15 different pairs of boots.

Elly brown shares how to style ankle boots with skinny jeans

Okay, that’s all for now. I know this is a bit lengthy, but I want to make sure I give you all the tools you need visually and written out! I really love creating these BYOW posts, and I hope you’re enjoying them and learning too to make the best out of your closet! Tag me when you style your outfits!!



Thank you for stopping by, have a great day!








Load Comments (1)
0 0 votes
Article Rating
Notify of
1 Comment
Newest Most Voted
Inline Feedbacks
View all comments
Jonathon Anderson

Thanks for sharing this article with us. I really like your advice and also the information that you have provided in this article. It has helped me a lot to find out about the boot styles of different brands and their features, which is very important for my wife’s shopping purpose.