How To Wear Over-The-Knee Boots This Winter

Happy #fashionwednesday! It FINALLY dropped to chilly weather this week. It was 70 up until yesterday when it got to around 40 and it should stay here for the foreseeable future. I loved being able to get out my fun wool jacket and over-the-knee boots. I haven’t actually owned a pair of this type of boot before so it was so fun for me to be able to style it and feel classy as all get out. These boots are SO COMFORTABLE and I highly recommend you snag yourself a pair ASAP. Let’s dive in to this.


How To Wear Over-The-Knee Boots This Winter

The jacket + boots in this post were sent to me for organic consideration from Soft Surroundings. All opinions are mine and mine alone.

How To Wear Over-The-Knee Boots This Winter

Pick a pair that fits your body length.

This may seem silly – but not all over-the-knee boots are created equal. If you have shorter legs, a super long pair of over-the-knee boots just won’t work for you. They will literally swallow your entire leg whole and look like upside down pants. NO bueno. SO. In order for this trend to work for you, you’ve gotta get a shorter pair of over-the-knee boots so that they just barely graze the top of your knee. That way, you still see your thighs and you rock the trend without losing length. If you’re taller or average height, the majority of over-the-knee boots will work for you (praise the height gods). These are a fairly tall pair of over-the-knee boots, and I sit at about 5’6. If my 5’0 sister wore them, however, they’d look really silly. They cover my entire knee and are tight up my calves.

How To Wear Over-The-Knee Boots This Winter

Pick a pair that fits your calves.

This is a tough one. My sister joked yesterday that she could never wear these because she has muscular calves – but she totally could because of the fact that these particular pair of boots have lace up backs. hallelujah, amiright? I have smaller calves (I know – I’m working on it. #upinthegym #justworkinonmyfitness), so I actually had to tighten them when I received them. But if you are of average calve size, you most likely won’t need to adjust them and if you have wider calves, you have the option to loosen them up. They’re SO versatile. The ties in the back also give them a unique look so they stand out in a crowd!

How To Wear Over-The-Knee Boots This Winter

Throw on a wool jacket & fitted turtle neck to look SO CHIC.

To complete this outfit, I opted for a black fitted turtle neck that flatters my torso and was on the shorter side. I chose this because my over-the-knee boots go above my knee, and I wanted to give my legs as much length as possible. With my top being shorter, you see almost all of my jeans up to the waist band. That gives the illusion my legs are longer than they actually are. I threw on my maroon + black gingham wool jacket for some color (I wasn’t trying to match kim possible, ya feel?) and threw on a pair of oversized statement earrings. You can also opt for a large statement necklace but I felt the jacket and boot combo kind of spoke for itself. 

How To Wear Over-The-Knee Boots This Winter

I really love this outfit. It is SO cute on and is incredibly easy to throw together. I had several people compliment me yesterday and I had to laugh because it took approx. 2 seconds to choose this outfit. If you are wondering what kind of warm holiday colors you should be wearing, it’s always a safe bet to go with black! It’s slimming, universally flattering and always looks professional. 

How To Wear Over-The-Knee Boots This Winter

Let me know what you think of this outfit in the comments below!! 

About The Author

Taylor Mobley


  1. Becca | 6th Dec 17

    Such a cute outfit!!

  2. Mel | 6th Dec 17

    My fav thing to wear in the winter!

  3. Sam | 6th Dec 17

    Love that jacket! So festive and perfect for the season!

  4. Lily | 6th Dec 17

    Gorgeous lady! I love these boots and that cute jacket!

  5. cara | 6th Dec 17

    Could you be any cuter?! Seriously loving both those boots and the jacket! So perfect for the season!

  6. Beth | 6th Dec 17

    That’s a great outfit! It looks warm! I love my over-the-knee boots. I feel great when I wear them ๐Ÿ™‚

    Beth ||

  7. Nikki Vergakes | 6th Dec 17

    I want a pair so badly!

  8. Krystin | 6th Dec 17

    These look gorgeous on you! I’m looking for a new pair so thanks for sharing!

  9. Jenny | 6th Dec 17

    Those boots are so cute on you! I love my OTK boots.

  10. Christina | 6th Dec 17

    Love these OTK boots! I love that coat too.

  11. Kristen Jones | 6th Dec 17

    I need to get another pair of OTN boots! I just love the lace up detail on the back!

  12. Alison @ Puppies & Pretties | 6th Dec 17

    I’m loving this entire outfit! I hear you on the right height for OTK boots. I am a bit taller (5’8″ ish) but so many boots that I’ve tried on are pretty much knee height. Sigh. But I guess that means I have actual knee high boots ๐Ÿ™‚

  13. Kiara | 6th Dec 17

    I was in the same boat with thinking I couldnโ€™t wear over-the-knee boots because my calves are very muscular. But, I found a pair that fit perfectly! Love seeing how you styled these lace ones!

  14. Nikki Gwin | 6th Dec 17

    I love it and I want it! ha! I don’t have OTK boots yet and I NEED some!
    ๐Ÿ™‚ gwingal

  15. Mary Leigh | 6th Dec 17

    So pretty! I need to bring my boots back out this year. It’s just now getting some what cold enough here though! I love how you’ve styled these boots!

  16. Felicia | 6th Dec 17

    I love over the knee boots, I”m just so afraid I’ll look even shorter haha I’m already only 5′!

  17. Lecy | A Simpler Grace | 6th Dec 17

    I LOVE those boots! They look great with that outfit.

  18. kallie | 7th Dec 17

    I think we’re boot twins! I have almost identical ones and I wear them ALL OF THE TIME. so versatile.

  19. Monica | 7th Dec 17

    I’ve always thought about over-the-knee boots, but I haven’t had the courage to do them yet! Maybe this will be the year. ๐Ÿ™‚

  20. Melissa | 7th Dec 17

    I love the look of over the knee boots! So perfect for winter!

  21. Erica @ Coming Up Roses | 7th Dec 17

    You are only the cutest thing on the planet. You know that?

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