How To Wear Over The Knee Boots With A Skirt

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After all of those shopping posts, I need to take a five second break from talking all things holiday. Anyone else? Well, I hope so, because I decided to shift gears a little bit today and talk about how to wear over the knee boots with a skirt.

It’s so funny how these looks that are a basic part of my wardrobe now would have almost scandalized me just a few years ago. (Okay, well not scandalized, but you get my point.) Now though? Over the knee boots are such a basic part of my wardrobe, I don’t know how to get through winter or really any cold weather situation without them! And pairing them with a skirt just seems so second nature to me. So it only makes sense that I share all of the ways that I style the look over here too.

J.Crew Sweater (Similar, Similar)
J.Crew Skirt (Similar, Similar)
Sole Society Boots (Similar, Similar)

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J.Crew Sweater (Similar, Similar)
J.Crew Skirt (Similar, Similar)
Sole Society Boots (Similar, Similar)

How To Wear Over The Knee Boots With A Skirt

When you’re styling an OTK boot with a skirt you do have to be careful. You’re walking a pretty fine line with looking really cute and looking..well…let’s just say inappropriate. And you don’t come to this blog for those outfits, so let’s move on.

With Tights

I wear tights with over the knee boots A LOT now. When I first started wearing over the knee boots, I would only throw on a pair of tights in cold weather. I would typically wear a black pair of tights, which really helps to keep your look a little more conservative. Personally, I would stick to that if you’re wearing high boots to your office (if it’s okay for your office).

Lately though, I’ve discovered that I like wearing tights more frequently with all of my thigh high boots. Way back when, I had done a sponsored post for these tights (I refuse to call them nylons) that were amazing. Last year, I ordered a bulk pack of them, and once it get’s cold, I pull them out. You honestly can’t tell I’m wearing tights in them (I’m wearing them in these pictures!) and my legs look so much better. For some reason, it also makes the look with over the knee boots look better too.

Plus, in favor of tights, they add just one more layer to help protect your legs and nothing is wrong with that.

With A Long Cardigan

I love a good cardigan, but in this case, it’s the ultimate trick piece. Why? Well, it’s a distractor. Typically, with with an over the knee boot paired with a skirt, that tends to be the center of attention. But when a cardigan is placed over it, that ties the outfit together and becomes the focal point.

You can do a similar thing with a longer jacket like a trench. The trick though is to keep this layer slim and not bulky. That’s why a trench would work, but a long puffer wouldn’t.

With An Oversized Sweater

An oversized sweater actually goes back to a similar concept that I talked about in my colorblocking post. The oversized sweater balances out your smaller pieces on bottom. Additionally, since you’re wearing fitted boots, you balance that with the loose, over sized sweater. It’s why you can also pull over a loose dress with thigh high boots! They balance each other out perfectly.

A few examples of how to wear over the knee boots with skirts

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(And a few with loose dresses just to show you what I meant)

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Photos by Kimberly Graydon