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Should Your Knee High Boots Take a Hike?

January 20, 2022

There’s a little rumor going around that knee high boots are out of style. But it’s just not true. These boots were made for walking. And you can definitely keep them and wear them. So let’s talk about why it’s a myth that your knee high boots should take a hike. And then I’ll share a few pointers for wearing them stylishly this winter.

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Are Knee High Boots Out of Style?

Knee high boots are a wardrobe staple, especially if you live in a colder climate and want to wear dresses or skirts. Wardrobe staples never go out of style. So saying that knee high boots are out of style is akin to proclaiming that sweaters or t-shirts are out of favor. Sure, certain silhouettes or heel structures will look more in vogue than others. But I don’t think we’ll ever see the day when knee high boots are completely a no-go. We just need them too much.

And I’m seeing every kind of knee high boot imaginable on the store websites right now. Although, granted, the pickings are slim, as many are selling out with the passing of the season. But yes, you can absolutely still wear your riding boots as well as your dressier versions. I’m not seeing as much of the over-the-knee boots as we did a few years ago, but they’re still available.

Why I'm Keeping My Skinny Jeans
See the original post for details.

So why did we all hear that nasty rumor about knee high boots taking a hike? Because jean silhouettes have changed. As recently as last winter most of us were wearing skinny jeans almost exclusively. And, as I pointed out in this recent post, skinny jeans work great with riding and other knee high boots. Taller boots definitely saw more daylight when we were all sporting our skinnies every day.

Flannel Shirt Layered
See the original post for details.

But, while many of us are enjoying the new, more relaxed fit denim silhouettes, you can still wear your skinny jeans. They are not completely “out of style,” just less “of the moment.” And the skinny jeans still look great with tall boots.


You can also still enjoy wearing your tall boots with leggings…

Dress on the Move
See original post for details (dress no longer available).

dresses (especially sweater dresses!)…

Are Knee High Boots Out of Style?
cropped cashmere cardigan // skirt (similar and similar) // boots no longer available (similar) // necklace // earrings // bracelet // similar bag

and skirts. In fact, that’s where we’re going to land this discussion today. Because skirts are definitely trending in popularity this winter and beyond. Yes, you can expect to see skirts of all lengths and silhouettes this spring, summer and fall, too. And, at least while it’s cold outside, those skirts look fantastic with tall boots.

Are Knee High Boots Out of Style?
cropped cashmere cardigan // skirt (similar and similar) // boots no longer available (similar) // necklace // earrings // bracelet // similar bag

I wore this outfit last week when we dined at a nice restaurant in celebration of our 34th wedding anniversary. The outfit felt festive and feminine, but my black suede slouch boots kept me warm and toasty.

Are Knee High Boots Out of Style?

And, of course, those boots, also from Ann Taylor, sold out fast. I do love them because these are true slouch boots, meaning they don’t even zip. They just have a wide, flexible shaft so you can slip them on your foot and then they drape easily on your calf. Even my wide calves!

Cropped length sweater with skirt
cropped cashmere cardigan // skirt (similar and similar) // boots no longer available (similar) // necklace // earrings // bracelet // similar bag

I really haven’t worn skirts in a long time. I usually find them hard to navigate for some reason. But realizing that they are really trending and having so many of my readers request that I feature them, I decided to buy a few. I purchased this pleated skirt, which is still available, and this other slip skirt, also available in limited sizes. I plan to show different ways to wear both silhouettes over the coming months, so I guess you could say this is the first in that series.

Cropped length sweater with skirt

To keep the proportions right, I wore a cropped length cashmere cardigan with the midi length skirt and my knee high slouch boots. I’m wearing a v-neck camisole similar to this one under the cardigan for modesty. I did wear these tights, but you wouldn’t have to if you’re warm enough without them.

cropped cashmere cardigan // necklace // earrings // bracelet

I finished the outfit off with pretty jewelry and my black faux fur collar coat. My coat is about 20 years old, but I have no plan to replace it. Like my boots, it’s a wardrobe essential. And it’s still in style!

Black Coat
cropped cashmere cardigan // skirt (similar and similar) // boots no longer available (similar) // necklace // earrings // bracelet // similar bag

So should you tell you knee high boots to take a hike? Absolutely not! Keep wearing them with your skinny jeans, if you choose. Wear them with leggings, if that’s your thing. And definitely wear them with your favorite winter dresses and skirts. You’ll be oh so in style! Oooh! And you can debunk that silly myth for all your gal pals, too. Tell them those boots are still made for walking!

Skirt with Boots
cropped cashmere cardigan // skirt (similar and similar) // boots no longer available (similar) // necklace // earrings // bracelet // similar bag

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Blessed for My Day

Simple kindness. It’s something we expect to receive from others on the regular, but we often fail to share it with others. Jesus taught us that kindness goes beyond just “live and let live.” To be kind means to do good toward someone, especially someone who cannot or will not repay…in kind.

How can we show kindness to those closest to us today? We can listen patiently, attentively. We can ask genuine, thoughtful questions, inviting them to share more. We can serve them first and gladly go last ourselves. We can speak gently and be patient. Regardless of whether the other person will show us kindness instead, we can remember that God is kind to us every day. And that will compel us to do unto others as we’d like to be treated ourselves.

So whatever you wish that others would do to you, do also to them, for this is the Law and the Prophets. ~ Matthew 7:12

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xoxo, Kay
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11 thoughts on “Should Your Knee High Boots Take a Hike?

  1. The outfit you wore for your anniversary dinner is so pretty and sophisticated. I will definitely keep my knee high riding boots in my closet! Have a great day!

  2. I have 2 pairs of tall boots. One black and one brown pair. I still wear them with skinny jeans, leggings, skirts and a sweater dress I just bought last fall/winter season that you posted. I love tall boots with these items and besides, they keep you warm as you pointed out. You look great with long skirts and boots and you should wear them more.
    Yes, kindness to everyone is something we need to practice. Bless you.

  3. Last weekend my daughters and I were hostesses for a bridesmaids luncheon. Without planning, we all three wore sweater dresses and knee high boots. ?

  4. I agree with you about tall boots. I really like the chain skirt, black sweater, and tall boots. I live up here in the snow belt, Chardon, OH, and we have 15+ inches of snow and more expected. I wear cowboy boots, ropers, a lot with my jeans. I especially like my brown ones stitched with pink and pink skinny jeans! Have a kind day!

  5. Kay, once again you knocked it out of the park. I have a question for you though about something different. This may not be the place to ask this and if so I apologize. I received part of my Talbots order today. I was so excited when I took the jeans out of the package with the ribbon trim down the side~they are even nicer in person. I tried them on and they fit me perfectly in the waist but are too big in the hip area. Does this mean they are considered “curvy” fit and I need a regular fit or are all of Talbots jeans made this way? The reason I ask is because the shipping cost was pricey and now I’ll have to most likely pay shipping again to have them returned. I’m still waiting on part of my order so when that comes in I’ll make the decision if the pink t-shirt will need returned. Just trying to save some on shipping costs.
    I have read you mentioning Talbots often and was wondering if you are able to convey my concern to them. I know I would order from them much more frequently if the shipping wasn’t as much of a concern.

    Thank you.
    If this is not the place to be asking such things is there a place we are able to send our questions to you?


    1. Hi Juliet. I’m sorry to hear the jeans didn’t work for you. I’m not sure what size you ordered but it sounds like you ordered the curvy fit and need the regular? If you’re wanting to exchange them I would contact Talbots via phone with their customer service information. I’m sure they’ll want to help you out here. Just tell them what you told me. I don’t have any special inside track with them myself. But I am always pretty bold when dealing with these stores when it comes to customer service type things. They want your business and they want to do all they can to help you enjoy your purchase. So I would call and ask for them to take care of the shipping. I may be wrong, but I think they’ll want to do that.

  6. Kay,
    I think I have been adding an e to your name. Oops!
    Boots are a must in cold weather. Because my back can’t handle walking much with a higher heel I mainly wear 1-2 inch heels. How I wish I could wear your black pair with the blue skirt. So booties and my riding boots are my go-to with cooler temps.
    What a great find for art you have available. Seeking out good quality art is what I do during the summer fairs/exhibits and have bought a few here and there. Good memories are attached to each one.
    Thanks for your post.

  7. Love all the ourfits !! I’m from North West Canada, so knee high boots will always be in my wardrobe. We get to much ice, snow and cold windy days to settle for anything else.