How to Wear Over The Knee Boots (3 Ways)

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How to Wear Over The Knee Boots

I want to discuss how to wear over-the-knee boots in this article.

I’ll go through how to wear over-the-knee boots in three distinct ways.

This trend has been present for a long time. The fact that I purchased my over the knee boots in 2005 should give you some idea of how long they have been in circulation.

They don’t seem to be going anywhere, at least not that I can tell. They are, in fact, becoming higher and more fitting. A tiny bit of change is occurring in their height and shape.

However, they’re still going strong. You should not be concerned about purchasing a pair at this time.

If you feel you’re too old for these, don’t be afraid to try them. Just like with anything else, you must approach it strategically.

Think carefully and cautiously about your pairings. Because things with these boots in particular can go wrong very rapidly.

They are naturally very sexy, so you have to adjust the rest of your outfit to match that sexiness.

Let’s look at three alternative ways to wear over-the-knee boots.

Look 1

The first style involves pairing your over-the-knee boots with a legging, whether it’s made of imitation leather or real leather, or some type of black jean.

Given that your over the knee boots and the surrounding clothing will blend together, this will probably be the easiest thing for you to do.

Of course, this assumes that you have a pair in black. If you’re going to buy a pair, I’d strongly advise getting a black pair.

It is entirely up to you, your lifestyle, your feet, and your joints whether or not you purchase heels or flats.

Some of you are limited to flats because you are unable to wear heels. It’s alright. The flat boots look great.

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I have three pairs in black. I have one pair that is flat, one pair that is wedge-shaped, and one pair that has a chunky heel.

They are a touch less sexy than a stiletto due to the heel shape. If you choose to wear stilettos, you are going to need to be even more careful about what you pair them with.

The wedge boots, flat boots, and boots with a chunkier heel all offer a slightly more subdued appearance.

Invest in suede and black if you’re just going to buy one. I would buy a flat, a wedge, or a chunky heel. Again, it depends on your lifestyle and any potential foot or joint issues.

This first look is the safest. They blend in when you wear them with black, giving you a long, lean line. There is nothing too sexy about it at all.

You can wear it with a t-shirt and a blazer or a button-down shirt and a leather jacket. You could pull it off with a sweater, a blouse with a tie neck, or a silk blouse.

To balance the slim pants, you only need to add a tiny bit of volume to the top.

You get the gist of it. It’s a much simpler look with black or dark pants because it’s more subtle.

That is the look I would choose if you are wary of the trend.

Look 2

Taking things a bit farther is what the second look does. Wear a lighter jean or a classic blue jean instead of a dark pair of pants to really make the boot stand out.

When you want to take it to the next level, that would be another option; with option number two, the boots will stand out a little bit more and you’re making a bigger statement.

So the first choice is between that midnight blue jean or a dark color. The most safe option is that.

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You want the boots in option number two to stand out a little bit more. You can choose a blue jean with a lighter color or a classic style. The boots will stand up much more as a result of that.

Look 3

The third option is both the riskiest and most sexy.

Don’t try look number three if you’re anxious about it, don’t want to be over the top, and are concerned about your age.

There is no reason for you to perform look number three. I’m just giving you a choice of look number three.

This is what you do on a date night or if you’re feeling a little bit more bold and sexy.

You put on a skirt or dress that is one to three inches higher than the top of your boot. That serves as your reference point.

The distance between the bottom of the skirt or dress and the boot shouldn’t be very wide.

Because the more space you have there on the leg, the sexier it will look, and the more we’ll be leaning toward trashy, rather than classy.

Try a shift dress, an a-line dress, or a fit-and-flare dress with a slightly more feminine feel if you want to wear a dress or a skirt but want to be a bit more conservative about it.

A small portion of the sexiness will be lost if you do something that is a little looser and less fitting.


Finding a pair of boots that fit snugly around your calves would be difficult for you if you do have a wider calf.

To make sure that the size and fit match your calf circumference, I recommend measuring the widest area of your calf and double-checking the information on the website.

On the other hand, you can place an order for a pair that has a panel in the back that stretches with your leg. In this case, you won’t have to worry about the fit because the panel will stretch along with your leg.

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When wearing over the knee boots, you can be confused regarding flared or bootcut jeans. No!

It just doesn’t make any sense because if you put these jeans under your boots, it will produce all this extra thickness around your leg, and it will look lumpy and sloppy.

You must stick to skinny jeans, leggings, or dresses and skirts.

Do you wear pointy or round toe boots? My toes are mostly almond-shaped. They are a good medium. I feel the pointy toe on this boot is a bit excessive. The almond toe, however, is, in my opinion, somewhere in the middle.

You could then wonder if you could pair these boots with a dress or skirt that was actually longer than the boots.

Yes, you can, but if you do so, your legs will look bigger. So I personally don’t do it. However, there is no reason why you can’t.

what to wear with over the knee boots


  • Gloria

    Gloria is a top-performing fashion designer with more than eight years of experience in developing fashion concepts.

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