How to Wear Over-the-Knee Boots

Good morning, friends. Now that the turkey’s put away, the leftovers have been consumed, and the Black Friday/Cyber Monday madness is dying down, it’s officially time to start thinking about the holidays!

Many of my neighbors have decorated their homes, I’m greeted by an array of colorful lights as I drive down my street at night. We have a Christmas tree already set up in our living room that is my view from my desk all day, every day. I’m excited to spend December evenings decking the halls and wrapping presents while Alexa serenades us with Christmas music. I love this time of year!

Today we’re back with day 10 of 25 Days of Winter Fashion, and I’m partnering with Nordstrom to share some tips for buying and wearing the over-the-knee boot trend.

If the bootie is the biggest shoe trend going right now, the over-the-knee boot is surely a close second. Booties are definitely more practical and, perhaps, more versatile, but over-the-knee boots make a statement like no other — with the possible exception of a fabulous stiletto, but they introduce a whole other host of issues… namely, how to walk in them without looking like a drunk sailor or, worse yet, getting injured while crossing a cobblestone street. But I digress.

How to Wear Over-the-Knee Boots

Point being, over-the-knee boots (OTK boots for short) are my favorite way to update an outfit and make a statement without throwing all caution to the wind. OTK boots actually have a few practical purposes and eliminate a few of the complicated issues that arise with booties. For one thing, they keep your legs warm. I tend to be cold-natured, and over-the-knee boots add another layer when it’s cold outside.

How to Wear Over-the-Knee Boots

Jo-Lynne Shane, Fashion over 40 Blogger styling OTK Boots for Fall

They also eliminate the dreaded sock issue. I can’t tell you how many times I’ve had people ask me whether or not they can wear booties with socks, and the answer is that it depends. Don’t you hate that answer? I do.

Chestnut Suede OTK Boots

With OTK boots, socks are a non-issue. Wear them or not, it’s entirely up to you. In fact, they don’t even have to match, which is an awesome thing because I have an aversion to sorting socks. Long live disorganized housekeeping!

How to Wear Over-the-Knee Boots for Fall

The other thing I love about OTK boots is they work with any length of pant. You will definitely want to wear skinny jeans with your OTK boots so the boots pull on easily, but your jeans can be cropped, ankle-length, full length, or anything in between. It doesn’t matter.

STYLE TIP: If your jeans are long, simply create one large cuff and pull your socks on overtop the jeans to keep them smooth under your boots. Easy peasy!

My Favorite OTK Boots!

So now that I’ve sold you on over-the-knee boots the question is, which over-the-knee boots should you buy? (If I haven’t sold you on them yet, I will. Give me time… this post isn’t over yet.)

As with most matters of style, that depends largely on your personal style aesthetic and what you want to wear with them.

How to Wear Over-the-Knee Boots with Jeans

I am a huge fan of the style of OTK boot I’m wearing in today’s post. The nice thing about these boots is their versatility. They slip on easily over jeans, and you can also wear them with tights and a dress or skirt.

These have a 3½-inch stacked heel, which makes them a little dressier than a flat and a great compliment for sweater dresses and shift dresses, but the chestnut-colored suede and the chunky wood heel give them a slightly more rugged look that works well with jeans. (A suede-covered heel is a nice touch, but it tends to make the boots dressier, and it’s also not as durable.)

My Favorite OTK Boots!

And yes, if you are petite, you can probably wear OTK boots. My advice is to look for over-the-knee boots with a lower shaft. Most websites will give you a measurement so you can compare. There’s actually quite a variety of boot heights so that is something to consider for most of us.

I have long legs, but I’m not super tall, so I don’t care for the super-high OTK boots. I like the ones that are more mid-height, generally in the 19-20″ range. Some are as low as 18″ and some are as high as 23″, if that gives you an idea. These have a 20″ shaft.

How to Wear Over-the-Knee Boots

I also like how they are split in the back. Not only does this add interest, but it makes them more comfortable to move around in. I have a pair of black leather OTK boots, and they are gorgeous, but they aren’t split in the back, and they feel very stiff when I sit down. I’m hoping they will loosen up, but it’s just easier if they are open in the back. (If I were taller, it might not be an issue.)

How to Wear Over-the-Knee Boots

The other thing to look at is the circumference. I like my OTK boots to work with jeans or dresses, so I’ve learned that I need at least a 15″ circumference. I ordered a pair of mushroom suede OTK boots with a 14″ circumference, and they look great with dresses, but they are too tight to wear over jeans.

Mushroom Suede OTK Boots with a Swing Dress

If you have thicker calves, look for OTK boots with a wider calf circumference — 16″ or more. I love how easy it is to search the Nordstrom website and sort through the variables. In the instance of over-the-knee boots alone, you can drill down by calf width and shaft height as well as color, price, heel height, and more.

The other popular style of OTK boot is the stretch shaft with the tie in the back. Stuart Weitzman made the original, and many have copied him since.

Stuart Weitzman Lowland OTK Boots

These generally have a super high (23″) and super skinny (14″) boot shaft. I feel that they look best with dresses or over leggings. They can be worn over jeans, but I didn’t feel like they work for me.

For a dressier style, I also have the Halogen Noble that I styled in this post. Again, the split in the back helps make them more comfortable and allows them to fit over jeans as easily as bare legs or leggings. They’re taller than my chestnut boots, at 22″ inches.

Halogen Noble OTK Boots in Grey Suede

When wearing dresses with OTK boots, it is fine to go bare-legged if it’s warm enough, but tights work well too. I generally prefer to keep tights close to the color of the boots. I’ll be styling OTK boots with a dress later this week, and I’ll discuss more of the variables in that post.

Every woman is different, and you have to figure out what works for you as far as style, shaft height, and circumference, but I hope this gives you something to go by.

For today’s outfit, I wore jeans and a corduroy jacket with a faux shearling collar. I just wore a short-sleeve tee underneath, which makes this outfit more suited for fall, but it was a balmy 50 degrees the morning we took these pictures, so it worked. I also think this jacket would also be cute over a striped turtleneck (40% off!) for colder weather.

The website indicated that this jacket runs small and to size up if you’re in between sizes, so I ordered a medium, and it’s perfect, and I like that it has enough room to wear a sweater underneath if I want. I thought the corduroy was a fun alternative to a denim jacket or utility jacket, and the collar adds a nice contrast.

How to Wear Over-the-Knee Boots

This is the perfect outfit to wear shopping or to meet a friend for coffee. It’s the epitome of casual-chic, in my opinion. And who doesn’t want to be casual-chic!?!

This look may not work for a day at the office, but you can totally get away with this look for almost anything life throws at you during the week — a trip to the mall, volunteering at your kid’s school, lunch with a girlfriend, an evening meeting, or whatever else calls for dressed-up casualwear.

Corduroy Jacket with Faux Shearling Collar with OTK Boots and Jeans for Fall

shop the post

corduroy jacket with shearling collar // u-neck tee in Beige Rainy Day // similar skinnies (mine are the Emma, but it’s an older wash) // OTK boots // similar handbag (less expensive option) // earrings // similar necklace // nails: CND Oxblood

Be sure to visit Cyndi and see the winter outfit she’s styling today!

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25 Responses

  1. Love this casual look! This is exactly the type of outfit idea I’ve been looking for. It took me a long time to come over to the otk boot side, haha. I was convinced I couldn’t wear them with my height and calf size, but I want to wear them all the time now! I’m still trying to figure out proportions, but I’m getting there. I’m anxious to see more looks and maybe some tips with dresses (like dress length in relation to the boots).

    1. I’ve seen dresses with the OTK boots a lot of ways. I think it depends on body type and style of the dress and boots. Of course, so many variables! HA! The safe way to wear it is to allow an inch or two between the top of the boot and the bottom of the dress/skirt. I have seen them overlapping, but I don’t like that look so much.

      1. Variables, always variables! Lol
        It’s definitely been tricky for me, and I have yet to find the right combo since dresses are usually longer on me and the boot shaft taller. I have a casual holiday party coming up and was hoping to find something that works!

  2. I have to agree with you on all points, Jo-Lynne!!
    Even an old timer like me loves her OTK boots—especially for the warmth issue!
    Now if I could only get my mom to like them—I think she needs to see them on older women first because she still thinks “pretty Woman” when she sees them!!

    1. Haha! That’s why I started out with this chestnut color. These were my first pair of OTK boots, and I felt less “Pretty Woman” in them because of their casual, rugged styling.

      I finally invested in the black leather ones, and when I wore them with a dress to church, I was worried, so I SOSed a friend and asked her to come find me and tell me if I looked hoochie-mama. She assured me I was fine – her point was that they’re a high quality leather and look expensive, and that does make a difference, I think. This is a trend I don’t skimp on.

      1. I think you’re totally right on the quality part—especially when it comes to leather.
        And the funny thing, when I wear them with regular dresses, no one even knows that they are OTK—that’s how I tiptoed into it!!

  3. I have these boots but have yet to wear them…gotta do it! I’m wishing I got the mushroom colored ones the other day when they were on sale. At 5’2″ my super tall shaft black boots look like waders so I’ll probably give them to a tall friend who wears size 8 LOL! Thanks again for the inspiration!

  4. Thanks Jo-Lynne. I have avoided OTK boots because I have large calves. It is good to know that you can get a wider shaft. I might just be convinced…. 🙂

  5. I know the post was about the OTK boots, but I just wanted to say how cute your jacket is- that rich navy corduroy is really pretty on you- definitely a cute alternative to a denim Jean jacket!

  6. Thanks for all the tips, very helpful! Is there a number of boots that a woman can own? My husband counted mine , yikes…there were 11. I told him that was nothing I needed more, more styles, more colors….right???

    1. Ha! Tell him he’d die if he could see my closet. 😉 My 11-year-old daughter came in the other day and told me I have too many shoes. I told her there was no such thing.

      I really do love the idea of a minimalist closet, but every time I think I’m done, I find something else I think I need to complete a look. Occupational hazards, I guess!! I actually ordered the mushroom boots to style with this outfit (and to wear with white jeans b/c the pastels outfit I did seemed to need a lighter boot.) I was bummed when they were too tight to wear over jeans, but it turns out, I think these boots work fine with this, so maybe I should make do more often. Haha!

      1. You’re funny! Those boots are perfect with the outfit and they match the purse as well. We need boots/shoes and a seperate purse for EVERY outfit! I would not read a blog called minimalist closet lol! Keep up the good work!!

        1. Yes, see, I picked the purse to try to make the boots tie in. 🙂 I had a grey one in mind. See, so it worked! Maybe I should exercise my creativity more often.

          Thanks for the enabling, I mean, er, the encouragement! ????

  7. Jo-Lynne, what an informative post! Thank you! Even though they aren’t for me, I learned a lot. You look great, as usual.

  8. I do love your jacket. Such a rich color. I love the whole outfit and may copy it but with cognac riding boots. Still not convinced the OTK is suitable fir this sixty year old. ????

  9. Well, if you had asked me as recently as two weeks ago, I would have said this wasn’t for me (especially because I’m short). However, as you have said, a trend takes time to take hold. I wore my riding boots today and once looking at myself in the mirror, I realized I have plenty of “room” on the leg for the right OTK boot.
    Thanks for your series; I am enjoying it immensely!

  10. I absolutely LOVE your whole outfit – every part of it is just so perfect together. That blue color looks stunning on you (I also love your hair with the gentle wave!). You’re so right, it looks totally casual-chic!

  11. Whenever I think of OTK boots, I immediately think of Julia Roberts in Pretty Woman. You are the one of 2 ppl I’ve seen who can pull them off. I’m glad to see it is possible, but what are they like to wear all day long? Looks like something I would put on, leave the house, and then totally regret–counting the minutes until I could rip them off. Ha ha!!

    1. Amazingly, no! They aren’t uncomfortable at all. Again, I think buying quality helps. These in particular that I’m wearing in this post area very comfortable and soft inside and out. 🙂

  12. let me say how many over the knee boots I have.about 12 and I wear them every time I want to go out.no matter where I go.I just enjoy my over the knee boots.because I LOVE them!

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