Fall/Winter OTK Boots

Fall is in full swing & Winter will be here before we know it. That means it is time to start bringing out all of the layers to keep you warm as the temps drop. Over the knee (OTK) boots are one of my favorite things to wear during this time of year. I love them styled with dresses, jeans, & skirts. Today, I’m sharing a roundup of the cutest Fall/Winter OTK boots & two styled looks featuring over the knee boots to give you a few different styling ideas. There is also a fun, very easy to enter giveaway at the end of this post, so be sure to scroll ALL the way down so you can enter!


I’m sharing all the cutest over the knee boots for fall & winter. This style of boot helps you take your dresses or skirts into cooler weather & instantly upgrade any look. I have shorter legs, so I gravitate more towards OTK boots with heels. I’ve included both those with heels & flats below for you all to shop. I found boots in every price range & color, too!



Sharing a ton of cute Fall/Winter OTK boots & a few outfits featuring inspiration for how to style your over-the-knee boots.

OTK boots look so cute paired with skirts. I love styled them with a flowy or fitted skirt. I wore a cropped sweater tucked in to this skirt for a Fall date night look. You can also style longer skirts with OTK boots for when it’s even colder outside & you don’t necessarily want any part of your legs to be bare. Another option would be to wear a longer coat over this look so it can transition to winter! I’m wearing a size XS in the jacket & a 2 in the skirt, but a 0 in the skirt would have fit better, as it is flowy & has a relaxed fit.

Sweater // Skirt // OTK Boots // Bag // Layered Necklace // Evil Eye Necklace


Sharing a ton of cute Fall/Winter OTK boots & a few outfits featuring inspiration for how to style your over-the-knee boots.

I love the color & cable knit detail of this sweater dress. I belted it here, but it looks so cute without one, too. You can style it with leggings for a work look! I’m wearing a size XS in this sweater dress & it fits TTS. I love OTK boots & sweater dresses, because it’s such an effortless outfit. You can switch up how you style them with pieces like scarves, jackets, & hats to make the look feel different!

Sweater Dress // Scarf // OTK Boots // Bag // Layered Necklace // Evil Eye Necklace

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  1. 11.6.19

    So cute! Even though the OTK boots have been popular for years now, I still have yet to find my perfect pair! Will check out your recommendations! ❤️✨

    Charmaine Ng | Architecture & Lifestyle Blog

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