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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- see this post here on how to style and wear ankle boots with denim.

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 Some may argue these are out of style and outdated.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!




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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.